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  <link:labelLink xlink:role="http://www.xbrl.org/2003/role/link" xlink:type="extended">
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Accumulated Amortization</link:label>
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    <link:label id="lab_skwd_GlobalAgricultureMember_label_en-US" xlink:label="lab_skwd_GlobalAgricultureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Global Agriculture [Member]</link:label>
    <link:label id="lab_skwd_GlobalAgricultureMember_documentation_en-US" xlink:label="lab_skwd_GlobalAgricultureMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Global Agriculture</link:label>
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    <link:label id="lab_skwd_SMA1Member_label_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SMA1 [Member]</link:label>
    <link:label id="lab_skwd_SMA1Member_documentation_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">SMA1</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SMA1Member" xlink:href="skwd-20260331.xsd#skwd_SMA1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SMA1Member" xlink:to="lab_skwd_SMA1Member" xlink:type="arc" order="1"/>
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    <link:label id="lab_ecd_AwardTmgPredtrmndFlag_label_en-US" xlink:label="lab_ecd_AwardTmgPredtrmndFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Predetermined [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgPredtrmndFlag" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardTmgPredtrmndFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgPredtrmndFlag" xlink:to="lab_ecd_AwardTmgPredtrmndFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_019bdc32-ab5f-7d70-94e5-775328c250ac_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets [Axis]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent_019bdc32-ac19-75c6-b494-158c5346bdcc_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock based compensation percent</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Tax Expense (Benefit), Share-Based Payment Arrangement, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationShareBasedCompensationExcessTaxBenefitPercent"/>
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    <link:label id="lab_dei_EntityFileNumber_019bdc32-ac18-7dac-a488-0972183727c0_terseLabel_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
    <link:label id="lab_dei_EntityFileNumber_label_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFileNumber" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityFileNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFileNumber" xlink:to="lab_dei_EntityFileNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_019bdc32-ac94-72fe-acc0-3c82006d43c2_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional paid-in capital:</link:label>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional Paid-in Capital [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AdditionalPaidInCapitalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:to="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedMaturitySecuritiesMeasurementInput_019bdc32-ac19-7aeb-9976-6440a52e54f7_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, measurement input</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesMeasurementInput_label_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Measurement Input</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesMeasurementInput_documentation_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:href="skwd-20260331.xsd#skwd_FixedMaturitySecuritiesMeasurementInput"/>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax_019bdc32-ac18-7d0d-a9a6-d5d7dd07b348_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Reclassification adjustment for gains (losses) on securities no longer held, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Reclassification Adjustment from AOCI for Sale of Securities, Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TabularListTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tabular List, Table</link:label>
    <link:label id="lab_ecd_TabularListTableTextBlock_label_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tabular List [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TabularListTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TabularListTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TabularListTableTextBlock" xlink:to="lab_ecd_TabularListTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock_019bdc32-ab60-7b32-b174-8c711ca52ee2_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments</link:label>
    <link:label id="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Investments [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:to="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock_019bdc32-ac19-7868-8318-5b22ca86c2de_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Related Party Transactions</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Related Party Transactions [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommissionsPolicy_019bdc32-ac19-7b78-acac-d982180de626_terseLabel_en-US" xlink:label="lab_us-gaap_CommissionsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and Fee Income and Underwriting Fee Income</link:label>
    <link:label id="lab_us-gaap_CommissionsPolicy_label_en-US" xlink:label="lab_us-gaap_CommissionsPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commissions, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommissionsPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommissionsPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommissionsPolicy" xlink:to="lab_us-gaap_CommissionsPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrMember_019d20c6-513b-7a3a-bbd3-00babd780d69_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Secured Overnight Financing Rate (SOFR)</link:label>
    <link:label id="lab_us-gaap_SecuredOvernightFinancingRateSofrMember_label_en-US" xlink:label="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Secured Overnight Financing Rate (SOFR) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SecuredOvernightFinancingRateSofrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:to="lab_us-gaap_SecuredOvernightFinancingRateSofrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LicenseMember_019bdc32-ab60-761b-9646-de4fe2c8dd03_terseLabel_en-US" xlink:label="lab_us-gaap_LicenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Licenses</link:label>
    <link:label id="lab_us-gaap_LicenseMember_label_en-US" xlink:label="lab_us-gaap_LicenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">License [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LicenseMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LicenseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LicenseMember" xlink:to="lab_us-gaap_LicenseMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_FairValueByMeasurementBasisAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Basis [Axis]</link:label>
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    <link:label id="lab_us-gaap_OtherExpenses_019bdc32-ab5f-7ed3-ab97-bd37c8a3423c_terseLabel_en-US" xlink:label="lab_us-gaap_OtherExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other expenses</link:label>
    <link:label id="lab_us-gaap_OtherExpenses_label_en-US" xlink:label="lab_us-gaap_OtherExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherExpenses" xlink:to="lab_us-gaap_OtherExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToCompAxis_terseLabel_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation:</link:label>
    <link:label id="lab_ecd_AdjToCompAxis_label_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToCompAxis" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AdjToCompAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToCompAxis" xlink:to="lab_ecd_AdjToCompAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_019bdc32-ab5f-730e-a68d-4bef1201b25f_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock_019bdc32-ac18-7488-829a-c3da6147c14e_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party Transactions</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transactions Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RelatedPartyTransactionsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:to="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote</link:label>
    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_label_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_NamedExecutiveOfficersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:to="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SalesCommissionsAndFees_019d20d3-2c98-7685-990d-8ef4db38ec85_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_SalesCommissionsAndFees" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Commission and fee expenses</link:label>
    <link:label id="lab_us-gaap_SalesCommissionsAndFees_label_en-US" xlink:label="lab_us-gaap_SalesCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Sales Commissions and Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SalesCommissionsAndFees" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SalesCommissionsAndFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SalesCommissionsAndFees" xlink:to="lab_us-gaap_SalesCommissionsAndFees" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_019bdc32-ac19-7f44-ba9e-a0d30dd7bd6f_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and Fee Income and Underwriting Fee Income</link:label>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RevenueFromContractWithCustomerTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain_019bdc32-ac19-7b45-ab55-aa0dfee2b609_terseLabel_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Domain]</link:label>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain_label_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FinancingReceivablePortfolioSegmentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:to="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SyndicateMember_019d708a-505b-7724-8678-a0c20786300f_terseLabel_en-US" xlink:label="lab_skwd_SyndicateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate Capacity</link:label>
    <link:label id="lab_skwd_SyndicateMember_label_en-US" xlink:label="lab_skwd_SyndicateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate [Member]</link:label>
    <link:label id="lab_skwd_SyndicateMember_documentation_en-US" xlink:label="lab_skwd_SyndicateMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SyndicateMember" xlink:href="skwd-20260331.xsd#skwd_SyndicateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SyndicateMember" xlink:to="lab_skwd_SyndicateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefit_019bdc32-ac94-74f5-9be0-c52e920cb529_terseLabel_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income tax expense</link:label>
    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CurrentIncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_019bdc32-ab5f-70a6-9991-8498ad445c3d_terseLabel_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unsecured subordinated notes</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_label_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes [Member]</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_documentation_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnsecuredSubordinatedNotesMember" xlink:href="skwd-20260331.xsd#skwd_UnsecuredSubordinatedNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnsecuredSubordinatedNotesMember" xlink:to="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToCompAmt_terseLabel_en-US" xlink:label="lab_ecd_AdjToCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation, Amount</link:label>
    <link:label id="lab_ecd_AdjToCompAmt_label_en-US" xlink:label="lab_ecd_AdjToCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AdjToCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToCompAmt" xlink:to="lab_ecd_AdjToCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeAssetNotionalAmount_019bdc32-ac19-7281-ae29-e1e33621d75b_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative assets, notional amount</link:label>
    <link:label id="lab_us-gaap_DerivativeAssetNotionalAmount_label_en-US" xlink:label="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Asset, Notional Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeAssetNotionalAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DerivativeAssetNotionalAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeAssetNotionalAmount" xlink:to="lab_us-gaap_DerivativeAssetNotionalAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_019bdc32-ac19-77b5-80c9-a2e413c1aecc_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Options</link:label>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_label_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Option [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockOptionMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EmployeeStockOptionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeStockOptionMember" xlink:to="lab_us-gaap_EmployeeStockOptionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_019bdc32-ac18-7989-a9e1-9c3d03565281_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Antidilutive Securities [Axis]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Antidilutive Securities [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquity_019bdc32-ac19-7fe5-8198-3910328b9180_totalLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_019bdc32-ac19-7cfa-b2c5-5a7745eea9fd_periodStartLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Stockholders' equity beginning balance</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_019bdc32-ac19-728a-a080-b567c082b4c4_periodEndLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Stockholders' equity ending balance</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_label_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquity" xlink:to="lab_us-gaap_StockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_019bdc32-ab60-70df-afcf-515133e1ee96_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract_019bdc32-ac94-7498-9c5a-a369716217c7_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTradingPoliciesProcLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_InsiderTradingPoliciesProcLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:to="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_019bdc32-ac94-74e4-bad7-abaa38d4f204_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, shares authorized (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommonStockSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesAuthorized" xlink:to="lab_us-gaap_CommonStockSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagedPremium_019e038b-b0cf-74e9-abef-198d9aba2d0c_terseLabel_en-US" xlink:label="lab_skwd_ManagedPremium" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total managed premiums</link:label>
    <link:label id="lab_skwd_ManagedPremium_label_en-US" xlink:label="lab_skwd_ManagedPremium" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managed Premium</link:label>
    <link:label id="lab_skwd_ManagedPremium_documentation_en-US" xlink:label="lab_skwd_ManagedPremium" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managed Premium Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagedPremium" xlink:href="skwd-20260331.xsd#skwd_ManagedPremium"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagedPremium" xlink:to="lab_skwd_ManagedPremium" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_019bdc32-ab60-793c-be94-c209b404b14f_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale:</link:label>
    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Instruments, Financial Assets, Balance Sheet Groupings [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:to="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_019bdc32-ab5f-7ee8-9ba2-41f89ab0c3fd_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities and stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities and Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilitiesAndStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_019bdc32-ac94-7693-ad03-69ecad0a506a_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Market value of trust funds</link:label>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_label_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held under Reinsurance Agreements, Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsAsset"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:to="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax_019bdc32-ac18-73a1-85dd-0983ae9dd21a_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Gain (Loss), before Adjustment and Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_019bdc32-ab60-7a9f-984b-3b395d2c6b85_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums and commissions receivable, net</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Receivable, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:to="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CoverAbstract_label_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cover [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CoverAbstract" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_CoverAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CoverAbstract" xlink:to="lab_dei_CoverAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember_019bdc32-ab60-788d-8346-ae19b4cd5740_terseLabel_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Portion at Fair Value Measurement</link:label>
    <link:label id="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Portion at Fair Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PortionAtFairValueFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:to="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MaximumMember_019bdc32-ac18-7152-9b65-3b6059c1fb12_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">High</link:label>
    <link:label id="lab_srt_MaximumMember_label_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Maximum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_MaximumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MaximumMember" xlink:to="lab_srt_MaximumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss_019bdc32-ac94-70b2-94e3-f7fe32d2c695_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortized Cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, before Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife_019bdc32-ac94-7678-bc31-09c5bc85b362_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Estimated average useful life (in years)</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Asset, Useful Life</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetUsefulLife"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_019bdc32-ab5f-765e-9ae8-93ea1feddc15_terseLabel_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital</link:label>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_label_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital [Member]</link:label>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_documentation_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:href="skwd-20260331.xsd#skwd_MeasurementInputIncrementalCostOfCapitalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:to="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_019bdc32-ab5f-77f2-afe4-7769e5b59556_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_019bdc32-ab60-790d-9c66-298c40321571_periodEndLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Net, ending balance</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_019bdc32-ab60-7704-897b-b4d28a02aea1_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_019bdc32-ac19-71d6-aab4-100900954082_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available-for-sale and held-to-maturity, fair value</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:href="skwd-20260331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_NonPeoNeoAvgTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:to="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_019bdc32-ac94-7105-bed2-0c316ad15662_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument [Line Items]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentLineItems" xlink:to="lab_us-gaap_DebtInstrumentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums_019d7795-819d-7713-8573-3bd92614f8c6_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Unearned Premiums</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:href="skwd-20260331.xsd#skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:to="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote</link:label>
    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AdjToNonPeoNeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:to="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_019bdc32-ab60-7971-b7c9-8ef8b59192c8_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Direct premiums</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Direct Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DirectPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsEarned" xlink:to="lab_us-gaap_DirectPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated</link:label>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_NonRule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:to="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019bdc32-ac18-7cf1-9b80-0b6f0c2b880f_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Income before income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019bdc32-ac18-7d45-a0c7-0918e8797325_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income before income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations before Income Taxes, Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityShellCompany_019bdc32-ac94-7676-b4a0-a31db877d786_terseLabel_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:label id="lab_dei_EntityShellCompany_label_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityShellCompany" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityShellCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityShellCompany" xlink:to="lab_dei_EntityShellCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds_019d7782-3aa3-756a-bedd-befd7bb8caef_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Funds at Lloyd's</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Lloyd's Funds</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Lloyd's Funds</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:href="skwd-20260331.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:to="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTable_019bdc32-ab5f-7e29-b82c-18dc0b7b909f_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentTable_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentTable" xlink:to="lab_us-gaap_DebtInstrumentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StatementOfStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:to="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingSegmentsMember_019bdc32-ac19-70e4-abc9-a966cfe1d065_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingSegmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating Segments</link:label>
    <link:label id="lab_us-gaap_OperatingSegmentsMember_label_en-US" xlink:label="lab_us-gaap_OperatingSegmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Segments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingSegmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingSegmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingSegmentsMember" xlink:to="lab_us-gaap_OperatingSegmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardTmgMnpiCnsdrdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:to="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_019bdc32-ab5f-78a6-8bfa-5d5f1f7e458d_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations, Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeLossFromContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperations" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_019bdc32-ac94-7dda-b7ef-c89622e9308e_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_label_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Other [Member]</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_documentation_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Other</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:href="skwd-20260331.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:to="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_019bdc32-ab5f-7270-9880-5280d113a797_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalPeriodFocus" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentFiscalPeriodFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalPeriodFocus" xlink:to="lab_dei_DocumentFiscalPeriodFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_019bdc32-ac19-7690-b90c-1c71d1b2ce55_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and intangible assets, net</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets, Net (Including Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IntangibleAssetsNetIncludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Method</link:label>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardTmgMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMethodTextBlock" xlink:to="lab_ecd_AwardTmgMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AwardTypeAxis_019bdc32-ac94-7d76-8ee4-23afba78133f_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:label id="lab_us-gaap_AwardTypeAxis_label_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AwardTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AwardTypeAxis" xlink:to="lab_us-gaap_AwardTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HedgingRelationshipDomain_019bdc32-ac18-706f-ad92-02844d22313d_terseLabel_en-US" xlink:label="lab_us-gaap_HedgingRelationshipDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hedging Relationship [Domain]</link:label>
    <link:label id="lab_us-gaap_HedgingRelationshipDomain_label_en-US" xlink:label="lab_us-gaap_HedgingRelationshipDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedging Relationship [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HedgingRelationshipDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HedgingRelationshipDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HedgingRelationshipDomain" xlink:to="lab_us-gaap_HedgingRelationshipDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EnergyMember_019bdc32-ac18-765e-b17f-76d4110d860b_terseLabel_en-US" xlink:label="lab_skwd_EnergyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Energy Solutions</link:label>
    <link:label id="lab_skwd_EnergyMember_label_en-US" xlink:label="lab_skwd_EnergyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Energy [Member]</link:label>
    <link:label id="lab_skwd_EnergyMember_documentation_en-US" xlink:label="lab_skwd_EnergyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Energy</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EnergyMember" xlink:href="skwd-20260331.xsd#skwd_EnergyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EnergyMember" xlink:to="lab_skwd_EnergyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_019bdc32-ac94-7756-b27e-d00e17efa4cb_terseLabel_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_label_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_EquityMethodInvesteeNameDomain" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_EquityMethodInvesteeNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_EquityMethodInvesteeNameDomain" xlink:to="lab_srt_EquityMethodInvesteeNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_TradingSymbol_019bdc32-ac19-7e1c-8bbb-e5fd81c2481b_terseLabel_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:label id="lab_dei_TradingSymbol_label_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_TradingSymbol" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_TradingSymbol"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_TradingSymbol" xlink:to="lab_dei_TradingSymbol" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CollateralizedSecuritiesMember_019bdc32-ab60-796e-95b8-7288a706d784_terseLabel_en-US" xlink:label="lab_us-gaap_CollateralizedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_CollateralizedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CollateralizedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CollateralizedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CollateralizedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedSecuritiesMember" xlink:to="lab_us-gaap_CollateralizedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_019bdc32-ac94-70a1-b0a4-3709a755f0a3_terseLabel_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hospitality</link:label>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hospitality Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hospitality Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_HospitalityPortfolioSegmentMember" xlink:href="skwd-20260331.xsd#skwd_HospitalityPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_HospitalityPortfolioSegmentMember" xlink:to="lab_skwd_HospitalityPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnderwritingExpense_019bdc32-ac94-7618-8fe8-96da67f0296b_totalLabel_en-US" xlink:label="lab_skwd_UnderwritingExpense" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total underwriting expenses</link:label>
    <link:label id="lab_skwd_UnderwritingExpense_label_en-US" xlink:label="lab_skwd_UnderwritingExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting Expense</link:label>
    <link:label id="lab_skwd_UnderwritingExpense_documentation_en-US" xlink:label="lab_skwd_UnderwritingExpense" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Underwriting Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingExpense" xlink:href="skwd-20260331.xsd#skwd_UnderwritingExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnderwritingExpense" xlink:to="lab_skwd_UnderwritingExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_019bdc32-ac94-733b-9828-9bbaf8671513_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Intangible Assets and Goodwill</link:label>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Intangible Assets and Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation_019bdc32-ac19-7f70-b0d7-dee457e7bd17_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuance of shares (in shares)</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shares Issued, Shares, Share-Based Payment Arrangement, after Forfeiture</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:to="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_StockUnitsMember_019bdc32-ac18-7eec-ae06-1cf869a4f4bc_terseLabel_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock units</link:label>
    <link:label id="lab_skwd_StockUnitsMember_label_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Units [Member]</link:label>
    <link:label id="lab_skwd_StockUnitsMember_documentation_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Stock Units</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_StockUnitsMember" xlink:href="skwd-20260331.xsd#skwd_StockUnitsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_StockUnitsMember" xlink:to="lab_skwd_StockUnitsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressCityOrTown_019bdc32-ab60-7c88-805c-09928b42abc1_terseLabel_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:label id="lab_dei_EntityAddressCityOrTown_label_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressCityOrTown" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressCityOrTown"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressCityOrTown" xlink:to="lab_dei_EntityAddressCityOrTown" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_019bdc32-ab5f-7806-94a6-2615cc83ca99_totalLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:href="skwd-20260331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_019bdc32-ab5f-7295-ab8f-44e9e4aef263_terseLabel_en-US" xlink:label="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_label_en-US" xlink:label="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short Term Investment, Fair Value Disclosure</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_documentation_en-US" xlink:label="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Short Term Investment, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortTermInvestmentFairValueDisclosure" xlink:href="skwd-20260331.xsd#skwd_ShortTermInvestmentFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShortTermInvestmentFairValueDisclosure" xlink:to="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_NonPeoNeoAvgCompActuallyPaidAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:to="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_019bdc32-ac19-71bb-acca-2efc6054648f_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rate, First 8 Years</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period One [Member]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:href="skwd-20260331.xsd#skwd_DebtInstrumentFixedInterestRatePeriodOneMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:to="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_019bdc32-ac18-79a0-8f09-0b8f64295a66_terseLabel_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund II LP units</link:label>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_label_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund 2, L.P. [Member]</link:label>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_documentation_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund 2, L.P.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_HudsonVenturesFund2LPMember" xlink:href="skwd-20260331.xsd#skwd_HudsonVenturesFund2LPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_HudsonVenturesFund2LPMember" xlink:to="lab_skwd_HudsonVenturesFund2LPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Other Measure</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Other Measure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_CompActuallyPaidVsOtherMeasureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_019bdc32-ac19-7965-bb4a-ab26a34422eb_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, consideration transferred</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_019d7776-e210-74ff-84a1-f7e8e1460a84_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total consideration</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferred1_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationConsiderationTransferred1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:to="lab_us-gaap_BusinessCombinationConsiderationTransferred1" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_019bdc32-ac18-731f-b8d7-edc86192582a_terseLabel_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_label_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityEmergingGrowthCompany" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityEmergingGrowthCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityEmergingGrowthCompany" xlink:to="lab_dei_EntityEmergingGrowthCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019bdc32-ab5f-7efe-bf75-c1c63796956c_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Change in Fair Value as of Vesting Date of Prior Year Equity Awards Vested in Covered Year</link:label>
    <link:label id="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember_label_en-US" xlink:label="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Change in Fair Value as of Vesting Date of Prior Year Equity Awards Vested in Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember"/>
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    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_019bdc32-ac18-7592-b053-31d3e7159350_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt issuance costs</link:label>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_label_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Issuance Costs, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredFinanceCostsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredFinanceCostsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredFinanceCostsNet" xlink:to="lab_us-gaap_DeferredFinanceCostsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_019bdc32-ac94-744f-bad5-73a331bd7edc_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted cash</link:label>
    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_label_en-US" xlink:label="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RestrictedCashAndCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedCashAndCashEquivalents" xlink:to="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EnergySolutionsMember_019bdc32-ac19-71f3-af79-6e5e2832cfc0_terseLabel_en-US" xlink:label="lab_skwd_EnergySolutionsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Energy Solutions</link:label>
    <link:label id="lab_skwd_EnergySolutionsMember_label_en-US" xlink:label="lab_skwd_EnergySolutionsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Energy Solutions [Member]</link:label>
    <link:label id="lab_skwd_EnergySolutionsMember_documentation_en-US" xlink:label="lab_skwd_EnergySolutionsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Energy Solutions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EnergySolutionsMember" xlink:href="skwd-20260331.xsd#skwd_EnergySolutionsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EnergySolutionsMember" xlink:to="lab_skwd_EnergySolutionsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_019bdc32-ac94-7ec8-9837-79dd36d18840_periodStartLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_019bdc32-ac94-7d5c-b4c1-35701caa915b_periodEndLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NoninterestIncome_019d209b-b848-74a5-bee4-ba09eec9945a_totalLabel_en-US" xlink:label="lab_us-gaap_NoninterestIncome" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net commission and fee income</link:label>
    <link:label id="lab_us-gaap_NoninterestIncome_label_en-US" xlink:label="lab_us-gaap_NoninterestIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Noninterest Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NoninterestIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NoninterestIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NoninterestIncome" xlink:to="lab_us-gaap_NoninterestIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_019bdc32-ac19-7c87-805b-38beb7627808_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, shares outstanding (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_019bdc32-ac19-7580-bdc7-5bbebddb489e_periodStartLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Common shares balance at beginning of period (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_019bdc32-ac19-7556-944a-e824326f0242_periodEndLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Common shares balance at ending of period (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares, Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesOutstanding" xlink:to="lab_us-gaap_CommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceAbstract_label_en-US" xlink:label="lab_us-gaap_InsuranceAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InsuranceAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceAbstract" xlink:to="lab_us-gaap_InsuranceAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss_019bdc32-ac19-76d8-a0c2-7cdfa9a36e56_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Accumulated Unrecognized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense_019d7794-bb78-71cd-ac0a-1c52e9a22ce5_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and loss adjustment expenses</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability For Claims And Claims Adjustment Expense</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability For Claims And Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:href="skwd-20260331.xsd#skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:to="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock_019bdc32-ac19-7d99-b5cb-cb0c6b01c4a7_terseLabel_en-US" xlink:label="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage Loans</link:label>
    <link:label id="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans, Notes, Trade and Other Receivables Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:to="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTableTextBlock_019bdc32-ac18-7d45-a1b8-111d06afaf59_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Revenue</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DisaggregationOfRevenueTableTextBlock"/>
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    <link:label id="lab_skwd_FHLBLoanMember_019bdc32-ac94-7d17-a203-e749f3b3e3f8_terseLabel_en-US" xlink:label="lab_skwd_FHLBLoanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">FHLB Loan</link:label>
    <link:label id="lab_skwd_FHLBLoanMember_label_en-US" xlink:label="lab_skwd_FHLBLoanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">FHLB Loan [Member]</link:label>
    <link:label id="lab_skwd_FHLBLoanMember_documentation_en-US" xlink:label="lab_skwd_FHLBLoanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">FHLB Loan</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FHLBLoanMember" xlink:href="skwd-20260331.xsd#skwd_FHLBLoanMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FHLBLoanMember" xlink:to="lab_skwd_FHLBLoanMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_019bdc32-ac18-71e9-9311-e120841da2bd_terseLabel_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_label_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain on Sale of Other Investments</link:label>
    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_documentation_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gain on Sale of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GainOnSaleOfOtherInvestments" xlink:href="skwd-20260331.xsd#skwd_GainOnSaleOfOtherInvestments"/>
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    <link:label id="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dividends or Other Earnings Paid on Equity Awards not Otherwise Reflected in Total Compensation for Covered Year</link:label>
    <link:label id="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember_label_en-US" xlink:label="lab_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dividends or Other Earnings Paid on Equity Awards not Otherwise Reflected in Total Compensation for Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_DvddsOrOthrErngsPdOnEqtyAwrdsNtOthrwsRflctdInTtlCompForCvrdYrMember"/>
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    <link:label id="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock_019bdc32-ac18-7941-8493-05fb365a98ca_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Finite-Lived Intangible Assets, Future Amortization Expense</link:label>
    <link:label id="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Finite-Lived Intangible Assets, Future Amortization Expense [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract" xlink:to="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_019bdc32-ac19-7e75-99a6-7b6b141b46f1_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts payable and accrued liabilities</link:label>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounts Payable and Accrued Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:to="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_019bdc32-ac18-78a9-a6e3-af9142396b20_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:label id="lab_dei_EntityAddressPostalZipCode_label_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressPostalZipCode" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressPostalZipCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressPostalZipCode" xlink:to="lab_dei_EntityAddressPostalZipCode" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDeterminationDate_terseLabel_en-US" xlink:label="lab_ecd_RestatementDeterminationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement Determination Date</link:label>
    <link:label id="lab_ecd_RestatementDeterminationDate_label_en-US" xlink:label="lab_ecd_RestatementDeterminationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Determination Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDeterminationDate" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_RestatementDeterminationDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDeterminationDate" xlink:to="lab_ecd_RestatementDeterminationDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_019bdc32-ac18-71dc-8b02-07d9ed32598d_verboseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Income tax expense</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_019bdc32-ac19-7c0a-b2af-3b0d9eb0d0ab_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Margin</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Basis Spread on Variable Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentBasisSpreadOnVariableRate1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:to="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherAssets_019bdc32-ac94-7278-adc0-03dfcbe417b2_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_OtherAssets_label_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAssets" xlink:to="lab_us-gaap_OtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_019bdc32-ac94-7ff4-aec8-428127613023_periodStartLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_019bdc32-ac94-791f-8930-79abc9609dfd_periodEndLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_PnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Adjustments Service Cost</link:label>
    <link:label id="lab_ecd_PnsnAdjsSvcCstMember_label_en-US" xlink:label="lab_ecd_PnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Adjustments Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnAdjsSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PnsnAdjsSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnAdjsSvcCstMember" xlink:to="lab_ecd_PnsnAdjsSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DesignatedAsHedgingInstrumentMember_019bdc32-ac94-76c0-ae73-29c6e101fb33_terseLabel_en-US" xlink:label="lab_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Designated as Hedging Instrument</link:label>
    <link:label id="lab_us-gaap_DesignatedAsHedgingInstrumentMember_label_en-US" xlink:label="lab_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Designated as Hedging Instrument [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DesignatedAsHedgingInstrumentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:to="lab_us-gaap_DesignatedAsHedgingInstrumentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_019bdc32-ac19-7aa2-a2f1-0aac04510c82_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueByFairValueHierarchyLevelAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:to="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis_019bdc32-ac19-7924-89e2-90bb992984af_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hedging Relationship [Axis]</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedging Relationship [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:to="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_019bdc32-ac18-7bbe-b800-1a7c6882ad99_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Incurred, net of reinsurance, related to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract"/>
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    <link:label id="lab_us-gaap_OtherIncomeAndExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_OtherIncomeAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income and Expenses [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncomeAndExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherIncomeAndExpensesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncomeAndExpensesAbstract" xlink:to="lab_us-gaap_OtherIncomeAndExpensesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_019e08c3-b76c-720a-844b-250a9a39ed3a_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_label_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Acquired During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GoodwillAcquiredDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:to="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_019e0539-770a-7d36-946b-eaf4545017a1_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net cash paid in acquisition</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Businesses, Net of Cash Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:to="lab_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_019bdc32-ac93-7de3-bf5b-ccbfc7f71c8f_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash provided by deposit accounting</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_label_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments For) Deposit Accounting</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_documentation_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments For) Deposit Accounting</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:href="skwd-20260331.xsd#skwd_ProceedsFromPaymentsForDepositAccounting"/>
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    <link:label id="lab_ecd_AllTradingArrangementsMember_terseLabel_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Trading Arrangements</link:label>
    <link:label id="lab_ecd_AllTradingArrangementsMember_label_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Trading Arrangements [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllTradingArrangementsMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AllTradingArrangementsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllTradingArrangementsMember" xlink:to="lab_ecd_AllTradingArrangementsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Footnote</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjFnTextBlock_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_EqtyAwrdsAdjFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjFnTextBlock" xlink:to="lab_ecd_EqtyAwrdsAdjFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Vs Peer Group</link:label>
    <link:label id="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock_label_en-US" xlink:label="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Vs Peer Group [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TotalShareholderRtnVsPeerGroupTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:to="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_019bdc32-ac18-7dd0-b98f-e6fdc46d715a_terseLabel_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loans held-for-investment, term</link:label>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_label_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans Held-for-Investment, Term</link:label>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_documentation_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loans Held-for-Investment, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LoansHeldForInvestmentTerm" xlink:href="skwd-20260331.xsd#skwd_LoansHeldForInvestmentTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LoansHeldForInvestmentTerm" xlink:to="lab_skwd_LoansHeldForInvestmentTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommitmentsAndContingenciesDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePayable_019bdc32-ac18-7961-94f3-f616628d3fa3_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance and premium payables</link:label>
    <link:label id="lab_us-gaap_ReinsurancePayable_label_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePayable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsurancePayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePayable" xlink:to="lab_us-gaap_ReinsurancePayable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_019bdc32-ac19-7eca-b264-814b4cde768d_terseLabel_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinate Debt Due 2039</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_label_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes Due 2039 [Member]</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_documentation_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes Due 2039</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:href="skwd-20260331.xsd#skwd_UnsecuredSubordinatedNotesDue2039Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:to="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnrealizedGainLossOnOtherInvestments_019bdc32-ab60-7dfc-987a-30b398a7b3d3_terseLabel_en-US" xlink:label="lab_skwd_UnrealizedGainLossOnOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_UnrealizedGainLossOnOtherInvestments_label_en-US" xlink:label="lab_skwd_UnrealizedGainLossOnOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unrealized Gain (Loss) on Other Investments</link:label>
    <link:label id="lab_skwd_UnrealizedGainLossOnOtherInvestments_documentation_en-US" xlink:label="lab_skwd_UnrealizedGainLossOnOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unrealized Gain (Loss) on Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnrealizedGainLossOnOtherInvestments" xlink:href="skwd-20260331.xsd#skwd_UnrealizedGainLossOnOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnrealizedGainLossOnOtherInvestments" xlink:to="lab_skwd_UnrealizedGainLossOnOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_019bdc32-ac19-7507-9615-ffdf6b7e3c79_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided by operating activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Operating Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_019bdc32-ab60-7c74-a6dc-bf4f3c031202_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Change in receivable/payable for securities</link:label>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_label_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments For (Proceeds From) Sale and Collection of Securities</link:label>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_documentation_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments For (Proceeds From) Sale and Collection of Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:href="skwd-20260331.xsd#skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:to="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTerm_019bdc32-ac19-7a6b-b187-adc3da5893c1_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, term</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentTerm_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTerm" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentTerm" xlink:to="lab_us-gaap_DebtInstrumentTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable_019de30f-4692-77d0-b2fa-8c32bd51564e_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation [Table]</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_019bdc32-ac19-71f6-82e8-332de6798f25_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Joint Ventures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:to="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019bdc32-ab5f-7652-85d8-476d3cdc5d6f_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale, at fair value (net of allowance for credit losses of $6,500 and $7,000, respectively) (amortized cost of $2,208,212 and $1,848,755, respectively)</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019bdc32-ab5f-785d-94f3-1bae755507dd_netLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019bdc32-ab5f-7118-80a1-ff76c7ee1def_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019bdc32-ab5f-77b8-82fd-03399d90bd93_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_019bdc32-ab60-7f23-8319-d70bc0c5aa13_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Sales/Disposals</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Sales</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember_019bdc32-ac19-722f-9000-5b54301d02fd_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee or Group of Investees</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee or Group of Investees [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_019bdc32-ac19-7145-b52a-fbf2f7eb6199_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Equity Method Investments [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Equity Method Investments [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:to="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote</link:label>
    <link:label id="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock_label_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_EquityValuationAssumptionDifferenceFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:to="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoTotalCompAmt_label_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PeoTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoTotalCompAmt" xlink:to="lab_ecd_PeoTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_019bdc32-ac18-7e25-84c8-b1b35e52f7a5_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongtermDebtTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeAxis" xlink:to="lab_us-gaap_LongtermDebtTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss_019bdc32-ab5f-767d-9f57-5547caf0776b_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amortized cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale and Held-to-Maturity, Amortized Cost, before Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract_019d778d-e38a-7499-b42f-a6e4e575521b_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets acquired, excluding goodwill</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Asset [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear_019d77ba-310e-7618-9aea-2d18a46eb7fd_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Remainder of 2026</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Remainder of Fiscal Year</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseRemainderOfFiscalYear" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_Syndicate1971CapacityMember_019d77a8-7836-7bbb-b053-d11cd4b4df8a_terseLabel_en-US" xlink:label="lab_skwd_Syndicate1971CapacityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate 1971 capacity - with fees</link:label>
    <link:label id="lab_skwd_Syndicate1971CapacityMember_label_en-US" xlink:label="lab_skwd_Syndicate1971CapacityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate 1971 Capacity [Member]</link:label>
    <link:label id="lab_skwd_Syndicate1971CapacityMember_documentation_en-US" xlink:label="lab_skwd_Syndicate1971CapacityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate 1971 Capacity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_Syndicate1971CapacityMember" xlink:href="skwd-20260331.xsd#skwd_Syndicate1971CapacityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_Syndicate1971CapacityMember" xlink:to="lab_skwd_Syndicate1971CapacityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_019bdc32-ac94-73a3-b5ac-bb1ea4cdc091_terseLabel_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementEquityComponentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StatementEquityComponentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementEquityComponentsAxis" xlink:to="lab_us-gaap_StatementEquityComponentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ApolloMember_019d7081-878b-73b8-a952-ba647181df22_verboseLabel_en-US" xlink:label="lab_skwd_ApolloMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Apollo</link:label>
    <link:label id="lab_skwd_ApolloMember_label_en-US" xlink:label="lab_skwd_ApolloMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Apollo [Member]</link:label>
    <link:label id="lab_skwd_ApolloMember_documentation_en-US" xlink:label="lab_skwd_ApolloMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Apollo</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ApolloMember" xlink:href="skwd-20260331.xsd#skwd_ApolloMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ApolloMember" xlink:to="lab_skwd_ApolloMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AgencyAgreementMember_019bdc32-ac19-73a3-87d4-b372610b2f50_terseLabel_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agency agreement</link:label>
    <link:label id="lab_skwd_AgencyAgreementMember_label_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Agency Agreement [Member]</link:label>
    <link:label id="lab_skwd_AgencyAgreementMember_documentation_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Agency Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgencyAgreementMember" xlink:href="skwd-20260331.xsd#skwd_AgencyAgreementMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AgencyAgreementMember" xlink:to="lab_skwd_AgencyAgreementMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonRule10b51ArrAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Adopted</link:label>
    <link:label id="lab_ecd_NonRule10b51ArrAdoptedFlag_label_en-US" xlink:label="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonRule10b51ArrAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_NonRule10b51ArrAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrAdoptedFlag" xlink:to="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NumberOfReportableSegments_019bdc32-ac18-7bf9-8270-c483bb09816a_terseLabel_en-US" xlink:label="lab_us-gaap_NumberOfReportableSegments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of reportable segments</link:label>
    <link:label id="lab_us-gaap_NumberOfReportableSegments_label_en-US" xlink:label="lab_us-gaap_NumberOfReportableSegments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Reportable Segments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NumberOfReportableSegments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NumberOfReportableSegments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NumberOfReportableSegments" xlink:to="lab_us-gaap_NumberOfReportableSegments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityDisclosureTextBlock_019bdc32-ac18-70bf-af18-0d816db69b0b_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_VariableInterestEntityDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:to="lab_us-gaap_VariableInterestEntityDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ArenaSOPLPMember_019bdc32-ac18-7ccc-ab0b-ce9b11d5b8e8_terseLabel_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arena SOP LP units</link:label>
    <link:label id="lab_skwd_ArenaSOPLPMember_label_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Arena SOP LP [Member]</link:label>
    <link:label id="lab_skwd_ArenaSOPLPMember_documentation_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Arena SOP LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ArenaSOPLPMember" xlink:href="skwd-20260331.xsd#skwd_ArenaSOPLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ArenaSOPLPMember" xlink:to="lab_skwd_ArenaSOPLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressStateOrProvince_019bdc32-ac94-769f-a8f6-66ab0001df81_terseLabel_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:label id="lab_dei_EntityAddressStateOrProvince_label_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressStateOrProvince" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressStateOrProvince"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressStateOrProvince" xlink:to="lab_dei_EntityAddressStateOrProvince" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_019bdc32-ac18-79ae-9dcd-12483df5df4b_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Antidilutive Security, Excluded EPS Calculation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:to="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_019bdc32-ac19-7cb3-8d20-b21eac3b10e5_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectsOfReinsuranceLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:to="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LoansReceivableFairValueDisclosure_019bdc32-ac18-71d0-bb83-ddd0c0669e75_terseLabel_en-US" xlink:label="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_us-gaap_LoansReceivableFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans Receivable, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LoansReceivableFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LoansReceivableFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LoansReceivableFairValueDisclosure" xlink:to="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_IndividualAxis_terseLabel_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Individual:</link:label>
    <link:label id="lab_ecd_IndividualAxis_label_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Individual [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_IndividualAxis" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_IndividualAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_IndividualAxis" xlink:to="lab_ecd_IndividualAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NumberOfSubsidiaries_019e08b4-81dd-71d4-8f51-0cf22f3fe3bc_terseLabel_en-US" xlink:label="lab_skwd_NumberOfSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of subsidiaries</link:label>
    <link:label id="lab_skwd_NumberOfSubsidiaries_label_en-US" xlink:label="lab_skwd_NumberOfSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number Of Subsidiaries</link:label>
    <link:label id="lab_skwd_NumberOfSubsidiaries_documentation_en-US" xlink:label="lab_skwd_NumberOfSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number Of Subsidiaries</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NumberOfSubsidiaries" xlink:href="skwd-20260331.xsd#skwd_NumberOfSubsidiaries"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NumberOfSubsidiaries" xlink:to="lab_skwd_NumberOfSubsidiaries" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityDomain_019de310-8f59-74ec-817d-1d6ec2167402_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Domain]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityDomain_label_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxAuthorityDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxAuthorityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxAuthorityDomain" xlink:to="lab_us-gaap_IncomeTaxAuthorityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_019bdc32-ac93-79f0-8299-19523345698f_terseLabel_en-US" xlink:label="lab_skwd_SubordinatedDebtNetMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_label_en-US" xlink:label="lab_skwd_SubordinatedDebtNetMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subordinated Debt, Net [Member]</link:label>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_documentation_en-US" xlink:label="lab_skwd_SubordinatedDebtNetMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subordinated Debt, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SubordinatedDebtNetMember" xlink:href="skwd-20260331.xsd#skwd_SubordinatedDebtNetMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SubordinatedDebtNetMember" xlink:to="lab_skwd_SubordinatedDebtNetMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember_019d47f9-e8a0-70a5-aa5b-37c95edd437d_terseLabel_en-US" xlink:label="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Profit commission &amp; consortium overrider charged to Managed Syndicates</link:label>
    <link:label id="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember_label_en-US" xlink:label="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Profit Commission And Consortium Overrider Charged To Managed Syndicates [Member]</link:label>
    <link:label id="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Profit Commission And Consortium Overrider Charged To Managed Syndicates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:href="skwd-20260331.xsd#skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:to="lab_skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_019bdc32-ac19-7e52-b008-463ca9e64340_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Without single maturity date</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, without Single Maturity Date, Amortized Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:to="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_019bdc32-ab60-7af8-9b85-8b8efabcfb15_terseLabel_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_label_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityInteractiveDataCurrent" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityInteractiveDataCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityInteractiveDataCurrent" xlink:to="lab_dei_EntityInteractiveDataCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedGain_019bdc32-ac19-754a-8a2f-bc5f29b7e2c2_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedGain_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Realized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquitySecuritiesFvNiRealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:to="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal_019bdc32-ab5f-7fd3-9636-bada053b449b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period provision for credit losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, Credit Loss Expense (Reversal)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestCreditLossExpenseReversal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTable_019bdc32-ab60-7bbd-a004-8463a0c5d8fc_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Table]</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTable_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DisaggregationOfRevenueTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisaggregationOfRevenueTable" xlink:to="lab_us-gaap_DisaggregationOfRevenueTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019bdc32-ac94-78fc-a47d-54b55343867b_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables, net</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_019bdc32-ac94-7276-a68c-4f4f7e4961b8_totalLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Paid and Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SMA2Member_019bdc32-ac18-75a1-9f00-72f2e2b78e5e_terseLabel_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SMA2</link:label>
    <link:label id="lab_skwd_SMA2Member_label_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SMA2 [Member]</link:label>
    <link:label id="lab_skwd_SMA2Member_documentation_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">SMA2</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SMA2Member" xlink:href="skwd-20260331.xsd#skwd_SMA2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SMA2Member" xlink:to="lab_skwd_SMA2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCentralIndexKey_019bdc32-ac18-7233-bc86-ba8e196890e1_terseLabel_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:label id="lab_dei_EntityCentralIndexKey_label_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCentralIndexKey" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityCentralIndexKey"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCentralIndexKey" xlink:to="lab_dei_EntityCentralIndexKey" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoName_terseLabel_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:label id="lab_ecd_PeoName_label_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoName" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PeoName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoName" xlink:to="lab_ecd_PeoName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Revenues_019bdc32-ac19-79f6-9108-3e931d59f4d4_totalLabel_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total revenues</link:label>
    <link:label id="lab_us-gaap_Revenues_label_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Revenues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Revenues" xlink:to="lab_us-gaap_Revenues" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year</link:label>
    <link:label id="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_label_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:to="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingAggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_OutstandingAggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingAggtErrCompAmt" xlink:to="lab_ecd_OutstandingAggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019bdc32-ac18-7f84-815d-84d4e417051b_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_019bdc32-ac18-7922-92eb-9b8734dae5b0_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Losses and LAE</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_019bdc32-ac19-749f-87e8-84afbbe0b606_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Segment Reporting Information, by Segment [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Segment Reporting Information, by Segment [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:to="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_019bdc32-ac19-716a-bd58-035afc80fac0_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PremiumsWrittenNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenNet" xlink:to="lab_us-gaap_PremiumsWrittenNet" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardExrcPrice_terseLabel_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exercise Price</link:label>
    <link:label id="lab_ecd_AwardExrcPrice_label_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardExrcPrice" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardExrcPrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardExrcPrice" xlink:to="lab_ecd_AwardExrcPrice" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFilerCategory_019bdc32-ac19-7963-b015-12b0e5d183a4_terseLabel_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Filer Category</link:label>
    <link:label id="lab_dei_EntityFilerCategory_label_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Filer Category</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFilerCategory" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityFilerCategory"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFilerCategory" xlink:to="lab_dei_EntityFilerCategory" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate_019bdc32-ac19-7018-8b86-93d73a33c5ac_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income tax expense at federal statutory rate</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, at Federal Statutory Income Tax Rate, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree_019bdc32-ab5f-7ccf-95e7-28aa14fda0b9_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2029</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_019bdc32-ac94-783d-ae09-36df41820061_negatedTotalLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:href="skwd-20260331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_019bdc32-ab60-7fc7-a0b4-08bcbcb71ccc_periodStartLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Gross, beginning balance</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vesting Date Fair Value of Equity Awards Granted and Vested in Covered Year</link:label>
    <link:label id="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember_label_en-US" xlink:label="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Vesting Date Fair Value of Equity Awards Granted and Vested in Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:to="lab_ecd_VstngDtFrValOfEqtyAwrdsGrntdAndVstdInCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_019bdc32-ac94-7155-a89d-a712ffc731cd_totalLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total expenses</link:label>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_label_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Benefits, Losses and Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BenefitsLossesAndExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses" xlink:to="lab_us-gaap_BenefitsLossesAndExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_019bdc32-ac19-7162-88e3-da841dd2ec3f_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total gross written premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGross" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PremiumsWrittenGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGross" xlink:to="lab_us-gaap_PremiumsWrittenGross" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine1_019bdc32-ac19-7a22-b988-9817697533cb_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine1_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine1" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressAddressLine1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine1" xlink:to="lab_dei_EntityAddressAddressLine1" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine2_019bdc32-ac18-7cba-9109-8ed18a3013e1_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine2_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine2" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityAddressAddressLine2"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine2" xlink:to="lab_dei_EntityAddressAddressLine2" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_019bdc32-ab60-7bd2-9031-467fde954909_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated other comprehensive loss:</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">AOCI Attributable to Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_019bdc32-ab5f-7f1e-8789-587f90bf8732_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments [Domain]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InvestmentTypeCategorizationMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:to="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019bdc32-ac19-7aca-98ce-df62d44c6564_negatedPeriodStartLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2009/role/negatedPeriodStartLabel" xlink:type="resource" xml:lang="en-US">Less: reinsurance recoverable on unpaid claims, beginning of period</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019bdc32-ac19-7fdc-8f91-2e9879a8cf6a_periodEndLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Plus: reinsurance recoverable on unpaid claims, end of period</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019bdc32-ac19-7a27-9dce-31b0f7a2652a_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded unpaid losses and LAE</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:to="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Asset Acquisition, Transaction between Entities under Common Control, and Joint Venture Formation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationAndAssetAcquisitionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract" xlink:to="lab_us-gaap_BusinessCombinationAndAssetAcquisitionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue_019d7780-a001-7bdc-8043-fd0f166adba3_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale, at fair value</link:label>
    <link:label id="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue_label_en-US" xlink:label="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Fixed Maturity Securities, Available-for-sale, at fair value</link:label>
    <link:label id="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Fixed Maturity Securities, Available-For-Sale, At Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:href="skwd-20260331.xsd#skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:to="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_019bdc32-ac18-710b-9f9b-6105c1b60175_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivatives</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instruments and Hedging Activities Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock"/>
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    <link:label id="lab_ecd_AwardGrantDateFairValue_terseLabel_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value as of Grant Date</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_019bdc32-ac93-7217-901f-d146643e0967_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfDebtInstrumentsTextBlock"/>
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    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_019bdc32-ac93-7f8b-bc41-22014e96016b_terseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted effect of awards (in shares)</link:label>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionLineItems_019bdc32-ac19-7108-a336-f28d60943c1a_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Line Items]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionLineItems_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RelatedPartyTransactionLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionLineItems" xlink:to="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_FairValueHedgeAssetsAtFairValue_label_en-US" xlink:label="lab_us-gaap_FairValueHedgeAssetsAtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hedge Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueHedgeAssetsAtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueHedgeAssetsAtFairValue"/>
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    <link:label id="lab_dei_DocumentQuarterlyReport_019bdc32-ac19-7d7f-a13c-92d9d71e824a_terseLabel_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:label id="lab_dei_DocumentQuarterlyReport_label_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Quarterly Report</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_019bdc32-ac94-7a55-a4f6-389125b97e0f_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months"/>
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    <link:label id="lab_us-gaap_LongTermDebtFairValue_019bdc32-ac19-7306-b818-d0386d989fd1_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_label_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongTermDebtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtFairValue" xlink:to="lab_us-gaap_LongTermDebtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_019bdc32-ac19-7b69-aea4-a5b281034c51_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value Measurement Inputs and Valuation Techniques</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock"/>
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    <link:label id="lab_ecd_ChangedPeerGroupFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote</link:label>
    <link:label id="lab_ecd_ChangedPeerGroupFnTextBlock_label_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChangedPeerGroupFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ChangedPeerGroupFnTextBlock"/>
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    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_019bdc32-ac18-7e03-9777-c67dbe84f6d2_terseLabel_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_label_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_RepurchaseAgreementCounterpartyNameDomain"/>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019bdc32-ac19-7959-ad2b-7d1ec83a1270_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
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    <link:label id="lab_skwd_TermLoanCreditFacilityMember_019bdc32-ab5f-759d-9b5c-aca916a5bbed_terseLabel_en-US" xlink:label="lab_skwd_TermLoanCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Term Loan Credit Facility</link:label>
    <link:label id="lab_skwd_TermLoanCreditFacilityMember_label_en-US" xlink:label="lab_skwd_TermLoanCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Term Loan Credit Facility [Member]</link:label>
    <link:label id="lab_skwd_TermLoanCreditFacilityMember_documentation_en-US" xlink:label="lab_skwd_TermLoanCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Term Loan Credit Facility</link:label>
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    <link:label id="lab_us-gaap_InvestmentTypeAxis_019bdc32-ac18-772b-a7f3-d18fab724023_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Type [Axis]</link:label>
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    <link:label id="lab_us-gaap_Investments_019bdc32-ac94-7d5e-8271-e06d3922502b_totalLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total investments</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Investments"/>
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    <link:label id="lab_ecd_TrdArrIndTitle_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PeerGroupTotalShareholderRtnAmt"/>
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    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesGross_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Businesses, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquireBusinessesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireBusinessesGross" xlink:to="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenGrossAbstract_019bdc32-ab5f-72f9-89e8-7972cb96e307_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Written</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGrossAbstract_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Gross [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGrossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PremiumsWrittenGrossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGrossAbstract" xlink:to="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoMember_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO</link:label>
    <link:label id="lab_ecd_NonPeoNeoMember_label_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_NonPeoNeoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoMember" xlink:to="lab_ecd_NonPeoNeoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FeeIncome_019d477d-77c1-7611-a0db-6289f7da8de8_terseLabel_en-US" xlink:label="lab_us-gaap_FeeIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underwriting fee income</link:label>
    <link:label id="lab_us-gaap_FeeIncome_label_en-US" xlink:label="lab_us-gaap_FeeIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fee Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FeeIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FeeIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FeeIncome" xlink:to="lab_us-gaap_FeeIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments_019bdc32-ac19-7d15-b495-2fdd428640a4_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Change in short-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for (Proceeds from) Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsForProceedsFromShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:to="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_019bdc32-ab5f-7b50-9834-93719eabc152_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Accumulated Gross Unrealized Gain, before Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_019bdc32-ab60-7a6b-9dd8-9121debdde05_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjsMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjsMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_EqtyAwrdsAdjsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsMember" xlink:to="lab_ecd_EqtyAwrdsAdjsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnBnftsAdjFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Benefits Adjustments, Footnote</link:label>
    <link:label id="lab_ecd_PnsnBnftsAdjFnTextBlock_label_en-US" xlink:label="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Benefits Adjustments, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnBnftsAdjFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PnsnBnftsAdjFnTextBlock"/>
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    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_019bdc32-ac94-7a1c-b538-9b6433a329c8_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Line Items]</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DisaggregationOfRevenueLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisaggregationOfRevenueLineItems" xlink:to="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherIncome_019bdc32-ab5f-7abf-b87a-dcfb5531917f_terseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other income</link:label>
    <link:label id="lab_us-gaap_OtherIncome_019bdc32-ab5f-7922-8bfe-c6b9f5c51a48_verboseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Other income</link:label>
    <link:label id="lab_us-gaap_OtherIncome_label_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncome" xlink:to="lab_us-gaap_OtherIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingRecoveryCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_OutstandingRecoveryCompAmt"/>
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    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_019bdc32-ac19-764d-8c8a-1a333ccb6fe4_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentNameDomain" xlink:to="lab_us-gaap_DebtInstrumentNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_019bdc32-ac19-7046-be24-fa4eb6395e4d_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Liability for Unpaid Claims and Claims Adjustment Expense</link:label>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Liability for Unpaid Claims and Claims Adjustment Expense [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_ecd_RecoveryOfErrCompDisclosureLineItems_label_en-US" xlink:label="lab_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Recovery of Erroneously Awarded Compensation Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_RecoveryOfErrCompDisclosureLineItems"/>
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    <link:label id="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember_019bdc32-ab5f-7e85-b6e9-08787632b0fa_terseLabel_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Estimate of Fair Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EstimateOfFairValueFairValueDisclosureMember"/>
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    <link:label id="lab_us-gaap_ReportingUnitDomain_019bdc32-ab60-7c3c-873d-afd7549b1078_terseLabel_en-US" xlink:label="lab_us-gaap_ReportingUnitDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reporting Unit [Domain]</link:label>
    <link:label id="lab_us-gaap_ReportingUnitDomain_label_en-US" xlink:label="lab_us-gaap_ReportingUnitDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reporting Unit [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReportingUnitDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReportingUnitDomain"/>
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    <link:label id="lab_ecd_MnpiDiscTimedForCompValFlag_label_en-US" xlink:label="lab_ecd_MnpiDiscTimedForCompValFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">MNPI Disclosure Timed for Compensation Value [Flag]</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_019bdc32-ac19-7772-a3e2-d01ec871e57f_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after one year through five years</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract_019bdc32-ac19-747e-93c3-85c175b4caaa_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unrealized gains and losses on investments:</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Unrealized Gain (Loss) [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesUnrealizedGainLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:to="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets_019d7786-2ad3-7a9b-a21d-e6bbcb036cb5_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Deferred Tax Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_019bdc32-ac94-73df-8a6f-2f6e2d3b3bb2_terseLabel_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revenues:</link:label>
    <link:label id="lab_us-gaap_RevenuesAbstract_label_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenues [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenuesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RevenuesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenuesAbstract" xlink:to="lab_us-gaap_RevenuesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_019bdc32-ac94-7efa-91c5-322125b29cff_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after five years through ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost"/>
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    <link:label id="lab_skwd_NumberOfUSSubsidiaries_019d9e93-2d37-77ab-be59-70f6efd93276_terseLabel_en-US" xlink:label="lab_skwd_NumberOfUSSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number Of US Subsidiaries</link:label>
    <link:label id="lab_skwd_NumberOfUSSubsidiaries_label_en-US" xlink:label="lab_skwd_NumberOfUSSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number Of US Subsidiaries</link:label>
    <link:label id="lab_skwd_NumberOfUSSubsidiaries_documentation_en-US" xlink:label="lab_skwd_NumberOfUSSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number Of US Subsidiaries</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NumberOfUSSubsidiaries" xlink:href="skwd-20260331.xsd#skwd_NumberOfUSSubsidiaries"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NumberOfUSSubsidiaries" xlink:to="lab_skwd_NumberOfUSSubsidiaries" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019bdc32-ab5f-7aa9-8ea2-d3825a0a8e33_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated other comprehensive (loss) income</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillGross_019bdc32-ac18-79d1-a700-2c8237c919d4_verboseLabel_en-US" xlink:label="lab_us-gaap_GoodwillGross" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Goodwill, gross balance</link:label>
    <link:label id="lab_us-gaap_GoodwillGross_label_en-US" xlink:label="lab_us-gaap_GoodwillGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillGross" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GoodwillGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillGross" xlink:to="lab_us-gaap_GoodwillGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_019bdc32-ac19-7b78-ad91-3290f1d3db38_terseLabel_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_label_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:to="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_019bdc32-ac18-73ee-b6bf-fe5de7871754_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchases</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Purchases</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:type="arc" order="1"/>
    <link:label id="lab_country_BM_019de310-f4b0-7f90-a5bd-f762a58c79fd_terseLabel_en-US" xlink:label="lab_country_BM" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">BERMUDA</link:label>
    <link:label id="lab_country_BM_label_en-US" xlink:label="lab_country_BM" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">BERMUDA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_BM" xlink:href="https://xbrl.sec.gov/country/2025/country-2025.xsd#country_BM"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_BM" xlink:to="lab_country_BM" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentCreditSpreadAdjustment_019d9ef1-6e15-7f1d-ab1d-904ae1a83b2d_verboseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, variable rate</link:label>
    <link:label id="lab_skwd_DebtInstrumentCreditSpreadAdjustment_label_en-US" xlink:label="lab_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Credit Spread Adjustment</link:label>
    <link:label id="lab_skwd_DebtInstrumentCreditSpreadAdjustment_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Credit Spread Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:href="skwd-20260331.xsd#skwd_DebtInstrumentCreditSpreadAdjustment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:to="lab_skwd_DebtInstrumentCreditSpreadAdjustment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_019bdc32-ac18-7a2d-a527-bcfa28873ac3_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive (loss) income:</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost</link:label>
    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_label_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AggtPnsnAdjsSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:to="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_019bdc32-ab60-7c9d-85af-a1768b01ed1c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_019bdc32-ac19-771a-8e75-d70a1298846c_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets by Major Class [Axis]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets by Major Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition_019e0402-fc31-7046-8eab-7ac5db1411a2_negatedTerseLabel_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less: reinsurance recoverable on unpaid claims, beginning of period</link:label>
    <link:label id="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition_label_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments, After Acquisition</link:label>
    <link:label id="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition_documentation_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments, After Acquisition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:href="skwd-20260331.xsd#skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:to="lab_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MinimumMember_019bdc32-ac18-73e8-9fe4-cc330efca40f_terseLabel_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Low</link:label>
    <link:label id="lab_srt_MinimumMember_label_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Minimum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MinimumMember" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_MinimumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MinimumMember" xlink:to="lab_srt_MinimumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems_019bdc32-ac18-7a37-9f7a-5cc080c8210d_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts, Notes, Loans and Financing Receivable [Line Items]</link:label>
    <link:label id="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems_label_en-US" xlink:label="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounts, Notes, Loans and Financing Receivable [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccountsNotesAndLoansReceivableLineItems"/>
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    <link:label id="lab_ecd_CoSelectedMeasureName_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureName_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
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    <link:label id="lab_us-gaap_USGovernmentDebtSecuritiesMember_019bdc32-ac19-7655-af41-053ca886121c_terseLabel_en-US" xlink:label="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">U.S. government securities</link:label>
    <link:label id="lab_us-gaap_USGovernmentDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">US Government Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_USGovernmentDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_USGovernmentDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_USGovernmentDebtSecuritiesMember" xlink:to="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionsProFormaNetIncomeLoss_019d77bd-86aa-76b6-8c83-52b8ea526001_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionsProFormaNetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net Income</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionsProFormaNetIncomeLoss_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionsProFormaNetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Pro Forma Information, Pro Forma Income (Loss), after Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionsProFormaNetIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessAcquisitionsProFormaNetIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionsProFormaNetIncomeLoss" xlink:to="lab_us-gaap_BusinessAcquisitionsProFormaNetIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_019bdc32-ac19-79d8-af7e-4e413d6ff348_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueDisclosureItemAmountsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:to="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShortTermInvestmentsAndCashMember_019bdc32-ac18-7a97-9ef4-bc8d22f85932_terseLabel_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments and cash</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentsAndCashMember_label_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-term Investments And Cash [Member]</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentsAndCashMember_documentation_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Short-term Investments And Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortTermInvestmentsAndCashMember" xlink:href="skwd-20260331.xsd#skwd_ShortTermInvestmentsAndCashMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShortTermInvestmentsAndCashMember" xlink:to="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_019bdc32-ac18-724a-8df8-6b0af01ceaea_netLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Notes Payable &amp; Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureTextBlock" xlink:to="lab_us-gaap_DebtDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_terseLabel_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Available</link:label>
    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_label_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Securities Aggregate Available Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TrdArrSecuritiesAggAvailAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:to="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockAppreciationRightsSARSMember_terseLabel_en-US" xlink:label="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Appreciation Rights (SARs)</link:label>
    <link:label id="lab_us-gaap_StockAppreciationRightsSARSMember_label_en-US" xlink:label="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Appreciation Rights (SARs) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockAppreciationRightsSARSMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockAppreciationRightsSARSMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockAppreciationRightsSARSMember" xlink:to="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance_019d47c3-f4a9-7bfe-adc7-25e8e50a6935_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, covenant, limitation on additional indebtedness maximum</link:label>
    <link:label id="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance_label_en-US" xlink:label="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Limitation On Additional Indebtedness, Maximum with a Debt Balance</link:label>
    <link:label id="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Covenant, Limitation On Additional Indebtedness, Maximum with a Debt Balance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:href="skwd-20260331.xsd#skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:to="lab_skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillRollForward_019bdc32-ab60-7446-8d2d-04ded24f8690_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_GoodwillRollForward_label_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GoodwillRollForward"/>
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    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_019bdc32-ab5f-7c75-8098-64fee9fab8aa_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommitmentsAndContingenciesDisclosureTextBlock"/>
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    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019bdc32-ac94-7acd-aeb0-f52469452593_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019bdc32-ac94-744f-9c01-8b73be010363_totalLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Diluted weighted-average common share equivalents (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
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    <link:label id="lab_ecd_NonGaapMeasureDescriptionTextBlock_label_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_NonGaapMeasureDescriptionTextBlock"/>
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    <link:label id="lab_dei_EntitySmallBusiness_019bdc32-ac18-751c-876e-b7914870a94c_terseLabel_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:label id="lab_dei_EntitySmallBusiness_label_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntitySmallBusiness" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntitySmallBusiness"/>
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    <link:label id="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired_019bdc32-ac94-7f74-850f-7293a24e628e_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business combination, voting equity interest acquired, percentage</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Voting Equity Interest Acquired, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired"/>
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    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxDisclosureAbstract"/>
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    <link:label id="lab_us-gaap_OtherCostAndExpenseOperating_019bdc32-ab5f-709b-8e0f-6207e848ea83_terseLabel_en-US" xlink:label="lab_us-gaap_OtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other operating and general expenses</link:label>
    <link:label id="lab_us-gaap_OtherCostAndExpenseOperating_label_en-US" xlink:label="lab_us-gaap_OtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Cost and Expense, Operating</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentTransitionReport" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentTransitionReport"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets_019d778c-52f7-7599-8dce-cc49d9eb2fc6_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_019bdc32-ac19-7df6-bdfe-59e7cef4bc89_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after one year through five years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue"/>
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    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_019bdc32-ab60-7645-82a0-e9d3da3997cb_terseLabel_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross realized losses</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_label_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Losses [Abstract]</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_documentation_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Losses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossRealizedInvestmentLossesAbstract" xlink:href="skwd-20260331.xsd#skwd_GrossRealizedInvestmentLossesAbstract"/>
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    <link:label id="lab_ecd_AwardUndrlygSecuritiesAmt_terseLabel_en-US" xlink:label="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Securities</link:label>
    <link:label id="lab_ecd_AwardUndrlygSecuritiesAmt_label_en-US" xlink:label="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Underlying Securities Amount</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardUndrlygSecuritiesAmt" xlink:to="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_019bdc32-ac18-7749-bff2-c845aabbd6b6_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityComponentDomain_019bdc32-ab5f-7598-9c26-1343041b0ce1_terseLabel_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityComponentDomain_label_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityComponentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityComponentDomain" xlink:to="lab_us-gaap_EquityComponentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentPeriodEndDate_019bdc32-ac18-76ca-a725-5fdcbeb7f9ce_terseLabel_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Period End Date</link:label>
    <link:label id="lab_dei_DocumentPeriodEndDate_label_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Period End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentPeriodEndDate" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentPeriodEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentPeriodEndDate" xlink:to="lab_dei_DocumentPeriodEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock_019bdc32-ac19-74ef-a768-cec8c0b8ee23_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Held-to-Maturity, Changes in Allowance for Credit Loss</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Allowance for Credit Loss [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_019bdc32-ac19-76a0-809c-c911f0fb2ad0_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:to="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromLinesOfCredit_019bdc32-ab5f-76cf-995e-dbd83619f229_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from long term borrowings</link:label>
    <link:label id="lab_us-gaap_ProceedsFromLinesOfCredit_label_en-US" xlink:label="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Lines of Credit</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromLinesOfCredit" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromLinesOfCredit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromLinesOfCredit" xlink:to="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:type="arc" order="1"/>
    <link:label id="lab_country_GB_019d47d1-44a3-781b-8b3a-5c4b3716e0ef_terseLabel_en-US" xlink:label="lab_country_GB" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">UK</link:label>
    <link:label id="lab_country_GB_label_en-US" xlink:label="lab_country_GB" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">UNITED KINGDOM</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_country_GB" xlink:href="https://xbrl.sec.gov/country/2025/country-2025.xsd#country_GB"/>
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    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Table</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardsCloseToMnpiDiscTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_019bdc32-ab60-7d6b-8d42-450d64d9fd6f_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans, at fair value</link:label>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_019bdc32-ab60-70ac-8987-33619636d0ff_verboseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total mortgage loans</link:label>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_label_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans on Real Estate, Commercial and Consumer, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet"/>
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    <link:label id="lab_dei_DocumentType_019bdc32-ac18-77c0-9865-6560a41f7012_terseLabel_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Type</link:label>
    <link:label id="lab_dei_DocumentType_label_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Type</link:label>
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    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_019bdc32-ac19-7d2e-85ef-6f2554803e29_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level 3</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 3 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel3Member" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueInputsLevel3Member"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract_019bdc32-ac94-7038-b38a-2883fffd7f99_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available for sale, fair value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract"/>
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    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_019bdc32-ac94-72ea-80e8-765aa30a907e_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earnings Per Share</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EarningsPerShareTextBlock"/>
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    <link:label id="lab_ecd_OutstandingRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
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    <link:label id="lab_us-gaap_AdditionalPaidInCapital_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional Paid in Capital</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AdditionalPaidInCapital"/>
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    <link:label id="lab_srt_ProductOrServiceAxis_019bdc32-ab5f-7f8c-8434-4c26b0530ae2_terseLabel_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and Service [Axis]</link:label>
    <link:label id="lab_srt_ProductOrServiceAxis_label_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service [Axis]</link:label>
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    <link:label id="lab_skwd_MortgageLoansMember_019bdc32-ac19-7ca8-9761-face8e70c43f_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_skwd_MortgageLoansMember_label_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans [Member]</link:label>
    <link:label id="lab_skwd_MortgageLoansMember_documentation_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage Loans</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansMember" xlink:href="skwd-20260331.xsd#skwd_MortgageLoansMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MortgageLoansMember" xlink:to="lab_skwd_MortgageLoansMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NotesPayable_019bdc32-ac19-7795-92f2-73222acb9a3f_terseLabel_en-US" xlink:label="lab_us-gaap_NotesPayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notes payable</link:label>
    <link:label id="lab_us-gaap_NotesPayable_label_en-US" xlink:label="lab_us-gaap_NotesPayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesPayable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NotesPayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NotesPayable" xlink:to="lab_us-gaap_NotesPayable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_019bdc32-ab60-722f-bd56-029a0d530ea9_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total commission and fee revenue</link:label>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer, Excluding Assessed Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_019bdc32-ac19-7a9e-a39b-5addebfd0b2c_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed premiums</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssumedPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsEarned" xlink:to="lab_us-gaap_AssumedPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_019bdc32-ac94-7273-827a-4a4d98634024_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeAxis_019bdc32-ab5f-7bc7-a261-74511d6c21f1_terseLabel_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:label id="lab_srt_RangeAxis_label_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeAxis" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_RangeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeAxis" xlink:to="lab_srt_RangeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1_019bdc32-ab5f-72f9-96dc-fe7a38766b4d_terseLabel_en-US" xlink:label="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1_label_en-US" xlink:label="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FinitelivedIntangibleAssetsAcquired1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:to="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage_019d47c8-0e5b-7958-ad26-b6e66ae8b8b4_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of credit facility, unused capacity, commitment fee percentage</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit Facility, Unused Capacity, Commitment Fee Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:to="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems_019bdc32-ac19-73ea-aba5-d2fdbe6d37af_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Line Items]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_AggtErrCompAmt_label_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompAmt" xlink:to="lab_ecd_AggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_019bdc32-ab60-7b32-834e-e8f9fc782b1d_terseLabel_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net unrealized gains (losses) on investments</link:label>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_label_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Unrealized Losses and Gains on Investments [Abstract]</link:label>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_documentation_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Net Unrealized Losses and Gains on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:href="skwd-20260331.xsd#skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:to="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote</link:label>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_label_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PeerGroupIssuersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:to="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019bdc32-ac19-7ac8-8fc4-81742cb76abc_totalLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total other comprehensive (loss) income</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019bdc32-ac19-7ceb-a06b-f8c944484dad_verboseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive (loss) income, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax, Portion Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent"/>
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    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_019bdc32-ac18-7770-ad92-4a04f652e076_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Useful life</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_label_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Difference in Net Assets, Amortization Period</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_documentation_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Difference in Net Assets, Amortization Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:href="skwd-20260331.xsd#skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:to="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue_019bdc32-ab5f-7c4b-bc17-72968bc99e3d_terseLabel_en-US" xlink:label="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Securities held as collateral, at fair value</link:label>
    <link:label id="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue_label_en-US" xlink:label="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Securities Held as Collateral, at Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SecuritiesHeldAsCollateralAtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:to="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_019bdc32-ac19-7692-8e21-3199088fe6d9_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level 1</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 1 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel1Member" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueInputsLevel1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel1Member" xlink:to="lab_us-gaap_FairValueInputsLevel1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable_019d7797-17d2-7a90-a2e1-9a60727eff24_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts payable and accrued liabilities</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Accounts Payable, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable"/>
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    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable_019bdc32-ab5f-7fce-b9ed-820e8e7a59c1_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Related Party Transactions, by Related Party [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Table]</link:label>
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    <link:label id="lab_us-gaap_EarningsPerShareDiluted_019bdc32-ac19-7247-946a-d76bb9b03c39_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings per share (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDiluted" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EarningsPerShareDiluted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDiluted" xlink:to="lab_us-gaap_EarningsPerShareDiluted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward_019bdc32-ac19-793b-a2eb-22befebab8a4_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Held-to-Maturity</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Allowance for Credit Loss [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_019bdc32-ac18-7881-96fe-adc90d9ca3c9_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after five years through ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery_019bdc32-ab5f-7577-b6c1-85f9f28a6ef9_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Recoveries of amounts previously written off</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, Allowance for Credit Loss, Recovery</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_019bdc32-ab60-7742-b0b2-5e4767f80873_negatedTerseLabel_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_label_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loss on Sale of Other Investments</link:label>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_documentation_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loss on Sale of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LossOnSaleOfOtherInvestments" xlink:href="skwd-20260331.xsd#skwd_LossOnSaleOfOtherInvestments"/>
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    <link:label id="lab_us-gaap_TreasuryStockCommonShares_019bdc32-ac94-7f1e-b474-4e23124985bc_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonShares" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockCommonShares_019dcf6b-e771-7529-b8d6-b8530dee7656_periodStartLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonShares" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Treasury Shares balance at beginning of period (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockCommonShares_019dcf6c-d039-7a3e-b960-c0cb180918ed_periodEndLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonShares" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Shares balance at Ending of period (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockCommonShares_label_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Common, Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockCommonShares" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_TreasuryStockCommonShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockCommonShares" xlink:to="lab_us-gaap_TreasuryStockCommonShares" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidationItemsDomain_019bdc32-ab60-76d2-be5c-6bd0d1fe6263_terseLabel_en-US" xlink:label="lab_srt_ConsolidationItemsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation Items [Domain]</link:label>
    <link:label id="lab_srt_ConsolidationItemsDomain_label_en-US" xlink:label="lab_srt_ConsolidationItemsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation Items [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidationItemsDomain" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_ConsolidationItemsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidationItemsDomain" xlink:to="lab_srt_ConsolidationItemsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract_label_en-US" xlink:label="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments, Debt and Equity Securities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:to="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_019bdc32-ac19-78b5-a4f9-86e2a61ff77b_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Other</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Joint Ventures Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestmentsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis_019bdc32-ac18-73e6-84a4-6b1e2dc872f5_terseLabel_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Axis]</link:label>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis_label_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FinancingReceivablePortfolioSegmentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:to="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium_019d7784-9a32-7374-a544-ae98cffad068_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Ceded Unearned Premium</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Ceded Unearned Premium</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:href="skwd-20260331.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium"/>
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    <link:label id="lab_skwd_SpecialtyProgramsMember_019bdc32-ac18-7c67-935b-e79feed648c0_terseLabel_en-US" xlink:label="lab_skwd_SpecialtyProgramsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Specialty Programs</link:label>
    <link:label id="lab_skwd_SpecialtyProgramsMember_label_en-US" xlink:label="lab_skwd_SpecialtyProgramsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Specialty Programs [Member]</link:label>
    <link:label id="lab_skwd_SpecialtyProgramsMember_documentation_en-US" xlink:label="lab_skwd_SpecialtyProgramsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Specialty Programs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SpecialtyProgramsMember" xlink:href="skwd-20260331.xsd#skwd_SpecialtyProgramsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SpecialtyProgramsMember" xlink:to="lab_skwd_SpecialtyProgramsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_019bdc32-ab60-7805-970f-cc3a6892f413_terseLabel_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_label_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Intangible Assets [Roll Forward]</link:label>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_documentation_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Total Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TotalIntangibleAssetsRollForward" xlink:href="skwd-20260331.xsd#skwd_TotalIntangibleAssetsRollForward"/>
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    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_019bdc32-ac19-7ab1-a66f-1f7ec0256800_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from the sales of equity securities</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_019bdc32-ac19-787a-bdf8-9797c68617e5_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Equity Securities, FV-NI</link:label>
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    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_019bdc32-ac19-7d91-b12e-38bab828e2bd_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash paid for income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_label_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Taxes Paid, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxesPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxesPaidNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxesPaidNet" xlink:to="lab_us-gaap_IncomeTaxesPaidNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo_019bdc32-ab5f-774a-bbfc-28bc54f6d923_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2028</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo"/>
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    <link:label id="lab_skwd_ApolloSegmentMember_019dbfca-35c3-7fff-a050-fba6fc915379_terseLabel_en-US" xlink:label="lab_skwd_ApolloSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Apollo Segment</link:label>
    <link:label id="lab_skwd_ApolloSegmentMember_label_en-US" xlink:label="lab_skwd_ApolloSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Apollo Segment [Member]</link:label>
    <link:label id="lab_skwd_ApolloSegmentMember_documentation_en-US" xlink:label="lab_skwd_ApolloSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Apollo Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ApolloSegmentMember" xlink:href="skwd-20260331.xsd#skwd_ApolloSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ApolloSegmentMember" xlink:to="lab_skwd_ApolloSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_019bdc32-ac19-74c9-9ab9-ae5d6465569f_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Principal</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:to="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_019bdc32-ac19-76bc-a7be-97aa4c1f5174_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rage Range [Axis]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Axis]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:href="skwd-20260331.xsd#skwd_DebtInstrumentFixedRatePeriodAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:to="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingAgencyFeePercentage_019d77c8-5a03-70c7-8c05-48c0a77c4546_terseLabel_en-US" xlink:label="lab_skwd_ManagingAgencyFeePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agency fees from syndicates (in percent)</link:label>
    <link:label id="lab_skwd_ManagingAgencyFeePercentage_label_en-US" xlink:label="lab_skwd_ManagingAgencyFeePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing Agency Fee Percentage</link:label>
    <link:label id="lab_skwd_ManagingAgencyFeePercentage_documentation_en-US" xlink:label="lab_skwd_ManagingAgencyFeePercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing Agency Fee Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingAgencyFeePercentage" xlink:href="skwd-20260331.xsd#skwd_ManagingAgencyFeePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingAgencyFeePercentage" xlink:to="lab_skwd_ManagingAgencyFeePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradeNamesMember_019d77ac-8246-73fb-b627-ab17e566a1f9_terseLabel_en-US" xlink:label="lab_us-gaap_TradeNamesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trade name</link:label>
    <link:label id="lab_us-gaap_TradeNamesMember_label_en-US" xlink:label="lab_us-gaap_TradeNamesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trade Names [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradeNamesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_TradeNamesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradeNamesMember" xlink:to="lab_us-gaap_TradeNamesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AgentRelationshipMember_019bdc32-ac94-7efc-93dc-ac8d1579e24f_terseLabel_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agent Relationships</link:label>
    <link:label id="lab_skwd_AgentRelationshipMember_label_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Agent Relationship [Member]</link:label>
    <link:label id="lab_skwd_AgentRelationshipMember_documentation_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Agent Relationship</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgentRelationshipMember" xlink:href="skwd-20260331.xsd#skwd_AgentRelationshipMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AgentRelationshipMember" xlink:to="lab_skwd_AgentRelationshipMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_019bdc32-ab60-75e8-b9fd-2d8c5c536f40_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrExpirationDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrExpirationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expiration Date</link:label>
    <link:label id="lab_ecd_TrdArrExpirationDate_label_en-US" xlink:label="lab_ecd_TrdArrExpirationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Expiration Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrExpirationDate" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TrdArrExpirationDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrExpirationDate" xlink:to="lab_ecd_TrdArrExpirationDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments_019bdc32-ab60-77b7-8dba-243237025b10_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Sales of and distributions from equity method and other long-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for (Proceeds from) Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsForProceedsFromLongtermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:to="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_019bdc32-ab60-7c72-acc3-94f283d352fa_verboseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Unrealized Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember_019dbf0a-2d3e-714e-b9a3-d89ca9fe460c_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non U.S government securities</link:label>
    <link:label id="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Security, Government, Non-US [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ForeignGovernmentDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:to="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_019bdc32-ab5f-712b-be3c-44df45fbb0c7_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Allowance for credit losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_019bdc32-ab5f-7699-8e01-13859881a1c5_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Allowance for Credit Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_019bdc32-ab5f-7957-b202-1e115f2677aa_periodStartLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_019bdc32-ab5f-7454-831e-610ec538e7ec_periodEndLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Allowance for Credit Loss, Excluding Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_019bdc32-ac94-7615-b54a-dde9d403eb1f_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Carrying Value of Equity Method Investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsWritten_019bdc32-ac18-7b85-81dc-6880202a688e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Ceded premiums</link:label>
    <link:label id="lab_us-gaap_CededPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CededPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsWritten" xlink:to="lab_us-gaap_CededPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_CompActuallyPaidVsNetIncomeTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCurrentReportingStatus_019bdc32-ab5f-7142-94ee-209702e3dfa6_terseLabel_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:label id="lab_dei_EntityCurrentReportingStatus_label_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCurrentReportingStatus" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityCurrentReportingStatus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCurrentReportingStatus" xlink:to="lab_dei_EntityCurrentReportingStatus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReceivablesAbstract_label_en-US" xlink:label="lab_us-gaap_ReceivablesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Receivables [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReceivablesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReceivablesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReceivablesAbstract" xlink:to="lab_us-gaap_ReceivablesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardsCloseToMnpiDiscTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_019bdc32-ac94-75e4-a040-a29512973166_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesDomain" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_ConsolidatedEntitiesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesDomain" xlink:to="lab_srt_ConsolidatedEntitiesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_019bdc32-ab5f-7ad5-8287-df8ec2396503_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due in less than one year</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_019bdc32-ac18-78fb-927a-31466cf8c0d9_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded paid losses and LAE</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables on Paid Losses, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsuranceRecoverablesOnPaidLossesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_019bdc32-ac19-7c79-abde-338621cef943_terseLabel_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agreement, ownership interest</link:label>
    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_label_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party, Ownership Interest</link:label>
    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_documentation_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Related Party, Ownership Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RelatedPartyOwnershipInterest" xlink:href="skwd-20260331.xsd#skwd_RelatedPartyOwnershipInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RelatedPartyOwnershipInterest" xlink:to="lab_skwd_RelatedPartyOwnershipInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialInstrumentAxis_019bdc32-ab5f-779d-a7f3-45db89d29039_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_FinancialInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FinancialInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentAxis" xlink:to="lab_us-gaap_FinancialInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfFinancialPositionAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Financial Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StatementOfFinancialPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:to="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ExecutiveCategoryAxis_terseLabel_en-US" xlink:label="lab_ecd_ExecutiveCategoryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Executive Category:</link:label>
    <link:label id="lab_ecd_ExecutiveCategoryAxis_label_en-US" xlink:label="lab_ecd_ExecutiveCategoryAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Executive Category [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ExecutiveCategoryAxis" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ExecutiveCategoryAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ExecutiveCategoryAxis" xlink:to="lab_ecd_ExecutiveCategoryAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019bdc32-ac18-73e9-91ff-6b220a9e6e0d_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_019bdc32-ac94-7017-947d-3d86d376b940_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from long term borrowings</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Issuance of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromIssuanceOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:to="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestExpense_019bdc32-ac19-70e8-a822-5f2bfe4649fe_terseLabel_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest expense</link:label>
    <link:label id="lab_us-gaap_InterestExpense_label_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Expense, Operating and Nonoperating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InterestExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestExpense" xlink:to="lab_us-gaap_InterestExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_019bdc32-ac19-7498-8b42-4bebf3ec55b7_terseLabel_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_label_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CurrentFiscalYearEndDate" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_CurrentFiscalYearEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CurrentFiscalYearEndDate" xlink:to="lab_dei_CurrentFiscalYearEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RealizedInvestmentLosses_019bdc32-ab5f-7e37-9f4a-7710bf95d091_negatedTotalLabel_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_RealizedInvestmentLosses_label_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Realized Investment Losses</link:label>
    <link:label id="lab_skwd_RealizedInvestmentLosses_documentation_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Realized Investment Losses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RealizedInvestmentLosses" xlink:href="skwd-20260331.xsd#skwd_RealizedInvestmentLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RealizedInvestmentLosses" xlink:to="lab_skwd_RealizedInvestmentLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019bdc32-ac94-720f-85bf-638671339f27_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_019bdc32-ab60-7f22-90cb-2b52fc2e9421_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rate, After Year 8</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period Two [Member]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:href="skwd-20260331.xsd#skwd_DebtInstrumentFixedInterestRatePeriodTwoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:to="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_019bdc32-ac19-7aba-8123-5c8103b09393_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_019bdc32-ac18-763c-bb3d-5ea75a2550fa_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock"/>
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    <link:label id="lab_us-gaap_ProfessionalFees_019bdc32-ac19-76b6-98cf-6d67f306c5ea_terseLabel_en-US" xlink:label="lab_us-gaap_ProfessionalFees" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Professional fees</link:label>
    <link:label id="lab_us-gaap_ProfessionalFees_label_en-US" xlink:label="lab_us-gaap_ProfessionalFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Professional Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProfessionalFees" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProfessionalFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProfessionalFees" xlink:to="lab_us-gaap_ProfessionalFees" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019bdc32-ac18-75a7-aa7e-dc6b6b9b8cfd_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior years</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Prior Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
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    <link:label id="lab_skwd_TransactionalESMember_019bdc32-ac19-7155-a9c9-dd146d287a02_terseLabel_en-US" xlink:label="lab_skwd_TransactionalESMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Transactional E&amp;S</link:label>
    <link:label id="lab_skwd_TransactionalESMember_label_en-US" xlink:label="lab_skwd_TransactionalESMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Transactional E&amp;S [Member]</link:label>
    <link:label id="lab_skwd_TransactionalESMember_documentation_en-US" xlink:label="lab_skwd_TransactionalESMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Transactional E&amp;S</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TransactionalESMember" xlink:href="skwd-20260331.xsd#skwd_TransactionalESMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TransactionalESMember" xlink:to="lab_skwd_TransactionalESMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_019bdc32-ac93-778d-ab0b-21329c95d7f2_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, held-to-maturity:</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale and Held-to-Maturity, Fair Value to Amortized Cost, after Allowance for Credit Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in Compensation Table</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in the Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:to="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_Syndicate1971Member_019d77d1-fea3-759a-bb74-d69daa5eaa3e_terseLabel_en-US" xlink:label="lab_skwd_Syndicate1971Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate 1971</link:label>
    <link:label id="lab_skwd_Syndicate1971Member_label_en-US" xlink:label="lab_skwd_Syndicate1971Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate 1971 [Member]</link:label>
    <link:label id="lab_skwd_Syndicate1971Member_documentation_en-US" xlink:label="lab_skwd_Syndicate1971Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate 1971</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_Syndicate1971Member" xlink:href="skwd-20260331.xsd#skwd_Syndicate1971Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_Syndicate1971Member" xlink:to="lab_skwd_Syndicate1971Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DepositContractsAssets_019bdc32-ac94-7c72-a2fc-fae39df69a02_verboseLabel_en-US" xlink:label="lab_us-gaap_DepositContractsAssets" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Deposit contracts, assets</link:label>
    <link:label id="lab_us-gaap_DepositContractsAssets_label_en-US" xlink:label="lab_us-gaap_DepositContractsAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deposit Contracts, Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepositContractsAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DepositContractsAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DepositContractsAssets" xlink:to="lab_us-gaap_DepositContractsAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_019bdc32-ac18-73cf-b090-4312f95ac192_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_019bdc32-ab5f-78db-a071-2d452133d0ff_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value, Assets and Liabilities Measured on Recurring Basis</link:label>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value, Assets and Liabilities Measured on Recurring Basis [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_019bdc32-ab5f-7dd1-8313-0c9e999c2f0d_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from the sales of fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale and Maturity of Marketable Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:to="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_019e0547-aa7e-7e3d-8b11-df3ce8659218_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Fair value of net assets acquired, excluding goodwill</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired to Liability Assumed, Excess (Less)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_019bdc32-ab5f-7743-a954-d54a1b3c2c79_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Antidilutive securities (in shares)</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount_019bdc32-ac94-792c-811c-5556bfa66896_terseLabel_en-US" xlink:label="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unrecorded unconditional purchase obligation</link:label>
    <link:label id="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount_label_en-US" xlink:label="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unrecorded Unconditional Purchase Obligation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:to="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CaptivesMember_019bdc32-ac19-7738-be57-290694c868bc_terseLabel_en-US" xlink:label="lab_skwd_CaptivesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Captives</link:label>
    <link:label id="lab_skwd_CaptivesMember_label_en-US" xlink:label="lab_skwd_CaptivesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Captives [Member]</link:label>
    <link:label id="lab_skwd_CaptivesMember_documentation_en-US" xlink:label="lab_skwd_CaptivesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Captives</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CaptivesMember" xlink:href="skwd-20260331.xsd#skwd_CaptivesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CaptivesMember" xlink:to="lab_skwd_CaptivesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ApolloGroupHoldingsLimitedMember_019d776c-6415-7645-a6ca-2bab637fce05_terseLabel_en-US" xlink:label="lab_skwd_ApolloGroupHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Apollo Group Holdings Limited</link:label>
    <link:label id="lab_skwd_ApolloGroupHoldingsLimitedMember_label_en-US" xlink:label="lab_skwd_ApolloGroupHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Apollo Group Holdings Limited [Member]</link:label>
    <link:label id="lab_skwd_ApolloGroupHoldingsLimitedMember_documentation_en-US" xlink:label="lab_skwd_ApolloGroupHoldingsLimitedMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Apollo Group Holdings Limited</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ApolloGroupHoldingsLimitedMember" xlink:href="skwd-20260331.xsd#skwd_ApolloGroupHoldingsLimitedMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ApolloGroupHoldingsLimitedMember" xlink:to="lab_skwd_ApolloGroupHoldingsLimitedMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_019bdc32-ac19-7b0a-b9bf-407b124c43da_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided by financing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Financing Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MeasureAxis_terseLabel_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measure:</link:label>
    <link:label id="lab_ecd_MeasureAxis_label_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureAxis" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_MeasureAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MeasureAxis" xlink:to="lab_ecd_MeasureAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeFairValueOfDerivativeNet_019bdc32-ac94-7ac1-9134-82b1ec39ac55_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivatives</link:label>
    <link:label id="lab_us-gaap_DerivativeFairValueOfDerivativeNet_label_en-US" xlink:label="lab_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative, Fair Value, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DerivativeFairValueOfDerivativeNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:to="lab_us-gaap_DerivativeFairValueOfDerivativeNet" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PvpTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure, Table</link:label>
    <link:label id="lab_ecd_PvpTableTextBlock_label_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PvpTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PvpTableTextBlock" xlink:to="lab_ecd_PvpTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_019bdc32-ac93-7feb-b6f4-4a9d1256f992_terseLabel_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Dowling Capital Partners LP units</link:label>
    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_label_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Dowling Capital Partners LP [Member]</link:label>
    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_documentation_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Dowling Capital Partners LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DowlingCapitalPartnersLPMember" xlink:href="skwd-20260331.xsd#skwd_DowlingCapitalPartnersLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DowlingCapitalPartnersLPMember" xlink:to="lab_skwd_DowlingCapitalPartnersLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_019bdc32-ac19-7131-a38e-f7d7ad3d8e43_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Investment expenses</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income, Investment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InvestmentIncomeInvestmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:to="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_019bdc32-ab60-7526-a393-4b5fdb68f851_terseLabel_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_label_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityTaxIdentificationNumber" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityTaxIdentificationNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityTaxIdentificationNumber" xlink:to="lab_dei_EntityTaxIdentificationNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_019bdc32-ac19-7377-99d4-9f878d61b5f5_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Without single maturity date</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, without Single Maturity Date, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock_019bdc32-ac19-7d41-b2ed-ed74d289008c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Assets And Liabilities</link:label>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Variable Interest Entities [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfVariableInterestEntitiesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:to="lab_us-gaap_ScheduleOfVariableInterestEntitiesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_019bdc32-ac94-75c4-8a1f-703979ae403b_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommonStockSharesIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesIssued" xlink:to="lab_us-gaap_CommonStockSharesIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_019bdc32-ab60-7829-b5c1-cc0cb2e7ccfb_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commercial mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commercial Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommercialMortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_019bdc32-ac18-7218-9993-aa6620eb2c7a_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and Intangible Assets</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill and Intangible Assets Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward_019bdc32-ab5f-7caf-835a-0c01708f64d5_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Available-For-Sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest, Allowance for Credit Loss [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfGoodwillTextBlock_019bdc32-ab5f-73d0-ad2b-b49772943041_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Goodwill</link:label>
    <link:label id="lab_us-gaap_ScheduleOfGoodwillTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfGoodwillTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfGoodwillTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfGoodwillTextBlock" xlink:to="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TradingArrAxis_terseLabel_en-US" xlink:label="lab_ecd_TradingArrAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Arrangement:</link:label>
    <link:label id="lab_ecd_TradingArrAxis_label_en-US" xlink:label="lab_ecd_TradingArrAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TradingArrAxis" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TradingArrAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TradingArrAxis" xlink:to="lab_ecd_TradingArrAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_TotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TotalShareholderRtnAmt" xlink:to="lab_ecd_TotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CorporateNonSegmentMember_019e0955-16cd-70f0-a635-a71531c26de6_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateNonSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Corporate expenses</link:label>
    <link:label id="lab_us-gaap_CorporateNonSegmentMember_label_en-US" xlink:label="lab_us-gaap_CorporateNonSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting, Reconciling Item, Corporate Nonsegment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateNonSegmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CorporateNonSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateNonSegmentMember" xlink:to="lab_us-gaap_CorporateNonSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_SecurityExchangeName_019bdc32-ac94-75e5-ac51-fbfcda1ea258_terseLabel_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:label id="lab_dei_SecurityExchangeName_label_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_SecurityExchangeName" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_SecurityExchangeName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_SecurityExchangeName" xlink:to="lab_dei_SecurityExchangeName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_019bdc32-ab5f-7b1e-a010-ee3395c6d245_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Allowance for credit losses</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsuranceRecoverablesAllowance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:to="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsEarned_019bdc32-ac18-7afa-bcda-116f6a2de039_negatedLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Ceded premiums</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CededPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsEarned" xlink:to="lab_us-gaap_CededPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_019bdc32-ab60-72e1-a4a8-1e5d2f7d2c7e_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain_019bdc32-ac19-7f76-b8a5-91a36b5912fc_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Class [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansUncollectableWriteOff_019bdc32-ac94-7bdf-a2bc-b5ee4de480cd_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansUncollectableWriteOff" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans uncollectable write-off</link:label>
    <link:label id="lab_skwd_MortgageLoansUncollectableWriteOff_label_en-US" xlink:label="lab_skwd_MortgageLoansUncollectableWriteOff" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans Uncollectable Write-Off</link:label>
    <link:label id="lab_skwd_MortgageLoansUncollectableWriteOff_documentation_en-US" xlink:label="lab_skwd_MortgageLoansUncollectableWriteOff" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage Loans Uncollectable Write-Off</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansUncollectableWriteOff" xlink:href="skwd-20260331.xsd#skwd_MortgageLoansUncollectableWriteOff"/>
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    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_019bdc32-ac94-7fe1-9ce4-47ff8403bef9_verboseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total losses for the period recognized in net investment gains</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Gain (Loss) Included in Earnings</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1"/>
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    <link:label id="lab_us-gaap_StatementLineItems_019bdc32-ab5f-7adf-9497-ab620f59968e_terseLabel_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statement [Line Items]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StatementLineItems"/>
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    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
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    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable"/>
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    <link:label id="lab_us-gaap_CommonStockMember_label_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommonStockMember"/>
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    <link:label id="lab_us-gaap_SignificantAccountingPoliciesTextBlock_019bdc32-ac18-7d47-8ea4-fcc8a76af1df_terseLabel_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Summary of Significant Accounting Policies</link:label>
    <link:label id="lab_us-gaap_SignificantAccountingPoliciesTextBlock_label_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Significant Accounting Policies [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SignificantAccountingPoliciesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:to="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeMember_019bdc32-ac19-787a-b172-499d0ca2302a_terseLabel_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:label id="lab_srt_RangeMember_label_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_RangeMember"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019bdc32-ac18-7fc8-9ed9-36bf7ba65318_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortized Cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019bdc32-ac18-743e-8cc3-a3f7a6c445b7_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019bdc32-ac19-72e1-bddf-ea051779bf8d_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior years</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prior Year Claims and Claims Adjustment Expense</link:label>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionAxis_019bdc32-ab5f-781a-84b8-e65aa4c41de9_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Axis]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionAxis_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RelatedPartyTransactionAxis"/>
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    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_019bdc32-ac94-7768-ba14-e6ec375a222f_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross, beginning balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets, Gross (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IntangibleAssetsGrossExcludingGoodwill"/>
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    <link:label id="lab_us-gaap_FairValueByAssetClassAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByAssetClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByAssetClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueByAssetClassAxis"/>
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    <link:label id="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember_019bdc32-ac18-7448-af09-ec5a6ecd4451_terseLabel_en-US" xlink:label="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents and Other Assets</link:label>
    <link:label id="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember_label_en-US" xlink:label="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents and Other Assets [Member]</link:label>
    <link:label id="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember_documentation_en-US" xlink:label="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents and Other Assets</link:label>
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    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_019bdc32-ac19-7978-9a8a-8c115098fb13_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_label_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Available-for-sale [Member]</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_documentation_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Available-for-sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:href="skwd-20260331.xsd#skwd_FixedMaturitySecuritiesAvailableForSaleMember"/>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:href="skwd-20260331.xsd#skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables"/>
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    <link:label id="lab_us-gaap_FederalFundsEffectiveSwapRateMember_019d47bb-b13a-7ab9-929a-4b68c2de3e74_terseLabel_en-US" xlink:label="lab_us-gaap_FederalFundsEffectiveSwapRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fed Funds Effective Rate Overnight Index Swap Rate</link:label>
    <link:label id="lab_us-gaap_FederalFundsEffectiveSwapRateMember_label_en-US" xlink:label="lab_us-gaap_FederalFundsEffectiveSwapRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fed Funds Effective Rate Overnight Index Swap Rate [Member]</link:label>
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    <link:label id="lab_us-gaap_EarningsPerShareBasic_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EarningsPerShareBasic"/>
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    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2025Member_documentation_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2025</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:href="skwd-20260331.xsd#skwd_RevolvingLineOfCreditDueDecember2025Member"/>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax_019bdc32-ac93-745f-9364-7a8936ec9b55_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Gain (Loss), before Adjustment, Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax"/>
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    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Segment Reporting Information, by Segment [Table Text Block]</link:label>
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    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_019bdc32-ac94-7a83-8c9a-e1be4d17a2a0_verboseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Indirect loans</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_019bdc32-ac94-73d5-9837-3bc8c3a7d5fb_terseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in indirect loans and loan collateral</link:label>
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    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountingPoliciesAbstract" xlink:to="lab_us-gaap_AccountingPoliciesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockCommonMember_019bdc32-ac19-7300-bc81-d1409eabe49e_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock:</link:label>
    <link:label id="lab_us-gaap_TreasuryStockCommonMember_label_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Common [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockCommonMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_TreasuryStockCommonMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockCommonMember" xlink:to="lab_us-gaap_TreasuryStockCommonMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PayVsPerformanceDisclosureLineItems_label_en-US" xlink:label="lab_ecd_PayVsPerformanceDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PayVsPerformanceDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PayVsPerformanceDisclosureLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PayVsPerformanceDisclosureLineItems" xlink:to="lab_ecd_PayVsPerformanceDisclosureLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageReceivablesMember_019bdc32-ac18-7a78-8f13-eff89844b187_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage Loans</link:label>
    <link:label id="lab_us-gaap_MortgageReceivablesMember_label_en-US" xlink:label="lab_us-gaap_MortgageReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Receivable [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageReceivablesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_MortgageReceivablesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageReceivablesMember" xlink:to="lab_us-gaap_MortgageReceivablesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_019bdc32-ac19-7852-899a-676b50a15327_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectsOfReinsuranceTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTable" xlink:to="lab_us-gaap_EffectsOfReinsuranceTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_019bdc32-ac94-7d8d-9908-e27551a5d965_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities:</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAbstract" xlink:to="lab_us-gaap_LiabilitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationDisclosureTextBlock_019d20ac-637c-7e74-abc8-8bb22589886e_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Acquisitions</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:to="lab_us-gaap_BusinessCombinationDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_019bdc32-ac94-764c-aa66-d0b190c33fc4_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity_019bdc32-ac18-71e8-9f49-68374911ba61_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Difference</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Difference Between Carrying Amount and Underlying Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:to="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable_019bdc32-ac18-7722-a7f4-dc427656e5be_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfVariableInterestEntitiesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:to="lab_us-gaap_ScheduleOfVariableInterestEntitiesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfCashFlowsAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Cash Flows [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StatementOfCashFlowsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:to="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_CoSelectedMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureAmt" xlink:to="lab_ecd_CoSelectedMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_019bdc32-ac19-745c-818b-fd079f659729_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_019bdc32-ac18-78b9-858d-885b55aaa953_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_MeasurementInputTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeAxis" xlink:to="lab_us-gaap_MeasurementInputTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MeasureName_terseLabel_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_MeasureName_label_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureName" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_MeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MeasureName" xlink:to="lab_ecd_MeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingAgentsFeesMember_019d47f8-c346-7247-8770-0c83ae1da0f8_terseLabel_en-US" xlink:label="lab_skwd_ManagingAgentsFeesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Managing agents fees</link:label>
    <link:label id="lab_skwd_ManagingAgentsFeesMember_label_en-US" xlink:label="lab_skwd_ManagingAgentsFeesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing Agents Fees [Member]</link:label>
    <link:label id="lab_skwd_ManagingAgentsFeesMember_documentation_en-US" xlink:label="lab_skwd_ManagingAgentsFeesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing Agents Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingAgentsFeesMember" xlink:href="skwd-20260331.xsd#skwd_ManagingAgentsFeesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingAgentsFeesMember" xlink:to="lab_skwd_ManagingAgentsFeesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_019bdc32-ac19-719a-b210-21245790c721_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due in less than one year</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue"/>
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    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues_019bdc32-ab5f-79f8-9429-87b3eb4be210_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuances</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Issuances</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_019bdc32-ac19-7592-acb0-1cb0a6a36466_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maturities, calls, transfers and paydowns of fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Maturities, Prepayments and Calls of Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward_019bdc32-ab5f-7f54-abc4-74700a0c20d8_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Finite-Lived</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsRollForward"/>
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    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilitiesNet_019d9e4b-d637-7173-939d-101aba42c239_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilitiesNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax liabilities</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilitiesNet_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilitiesNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Income Tax Liabilities, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxLiabilitiesNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredIncomeTaxLiabilitiesNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxLiabilitiesNet" xlink:to="lab_us-gaap_DeferredIncomeTaxLiabilitiesNet" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProfessionalLinesMember_019bdc32-ac18-7dfa-8a5b-c5d5ba238ef2_terseLabel_en-US" xlink:label="lab_skwd_ProfessionalLinesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Professional Lines</link:label>
    <link:label id="lab_skwd_ProfessionalLinesMember_label_en-US" xlink:label="lab_skwd_ProfessionalLinesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Professional Lines [Member]</link:label>
    <link:label id="lab_skwd_ProfessionalLinesMember_documentation_en-US" xlink:label="lab_skwd_ProfessionalLinesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Professional Lines</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProfessionalLinesMember" xlink:href="skwd-20260331.xsd#skwd_ProfessionalLinesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProfessionalLinesMember" xlink:to="lab_skwd_ProfessionalLinesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_019bdc32-ab5f-7b47-8ff3-93566409b4a2_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed premiums</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssumedPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsWritten" xlink:to="lab_us-gaap_AssumedPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_019bdc32-ac19-7e0d-b531-0d2abb5dc81e_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SUA fee income</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_label_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Fee Icome [Member]</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_documentation_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Fee Icome</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:href="skwd-20260331.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:to="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnsecuredDebtMember_019d9eb1-0904-7452-9a00-505691c5ab59_terseLabel_en-US" xlink:label="lab_us-gaap_UnsecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unsecured Debt</link:label>
    <link:label id="lab_us-gaap_UnsecuredDebtMember_label_en-US" xlink:label="lab_us-gaap_UnsecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unsecured Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnsecuredDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_UnsecuredDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnsecuredDebtMember" xlink:to="lab_us-gaap_UnsecuredDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019bdc32-ab5f-730f-a789-a8276a19b4c9_negatedTerseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="skwd-20260331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Assets_019bdc32-ac18-75f7-aebf-d0420ab24c47_totalLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total assets</link:label>
    <link:label id="lab_us-gaap_Assets_label_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Assets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Assets" xlink:to="lab_us-gaap_Assets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_019bdc32-ac18-7bb2-aa7b-341a7d46394c_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2027</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_019e0546-7105-78f9-a633-b65544b42934_verboseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Estimated Annual Amortization Expense</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_019bdc32-ac18-7312-a0fa-4d4efbc55dd2_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from operating activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Operating Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife_019d77b4-0136-73af-9b4b-d0f9d22e944e_terseLabel_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Estimated average useful life (in years)</link:label>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife_label_en-US" xlink:label="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Acquired Finite-Lived Intangible Assets, Weighted Average Useful Life</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:to="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableInterestEntityLineItems_019bdc32-ac19-7f63-a9c6-33390748cceb_terseLabel_en-US" xlink:label="lab_us-gaap_VariableInterestEntityLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Line Items]</link:label>
    <link:label id="lab_us-gaap_VariableInterestEntityLineItems_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_VariableInterestEntityLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableInterestEntityLineItems" xlink:to="lab_us-gaap_VariableInterestEntityLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour_019bdc32-ab5f-72e6-a3bb-e443737e716e_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2030</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesFairValue_019bdc32-ac18-74ef-935b-7b1501dde88d_verboseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesFairValue_019bdc32-ac18-7069-8e24-b51b8702ed68_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity securities, held-to-maturity</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_019bdc32-ab60-723f-8d19-211547e51418_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_label_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCommonStockSharesOutstanding" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityCommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCommonStockSharesOutstanding" xlink:to="lab_dei_EntityCommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_019bdc32-ac18-78e7-ba1d-996d75dcc29c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:to="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_019d778e-3141-725a-8d89-ee1ca456680b_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total assets acquired, excluding goodwill</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_019bdc32-ab5f-7471-8b80-10eec25cabcc_terseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_019bdc32-ab5f-74f4-b4fe-9d17fa0f1308_verboseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prepaid Reinsurance Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidReinsurancePremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PrepaidReinsurancePremiums"/>
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    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_019bdc32-ac19-7790-a5a1-0d4a4fd16e29_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level 2</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 2 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel2Member" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueInputsLevel2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel2Member" xlink:to="lab_us-gaap_FairValueInputsLevel2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_OtherSectorsMember_019bdc32-ac94-7bfd-b8f6-251e4fad9798_terseLabel_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_OtherSectorsMember_label_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Sectors [Member]</link:label>
    <link:label id="lab_skwd_OtherSectorsMember_documentation_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Sectors</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_OtherSectorsMember" xlink:href="skwd-20260331.xsd#skwd_OtherSectorsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OtherSectorsMember" xlink:to="lab_skwd_OtherSectorsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestments_019bdc32-ac19-7779-ad24-5dc0aea8335e_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_019bdc32-ac19-7ec5-b3ea-09fdcbc25858_netLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_019bdc32-ac19-7387-bb5a-9800c36e1488_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recorded investment balance</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestments" xlink:to="lab_us-gaap_EquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted</link:label>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted [Text Block]</link:label>
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    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_019bdc32-ab5f-7c74-87d4-fe38c813b89d_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Domain]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessAcquisitionAcquireeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:to="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredCedingCommission_019bdc32-ac18-7220-9a1a-6f2d4ea8a92f_terseLabel_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred ceding commission</link:label>
    <link:label id="lab_skwd_DeferredCedingCommission_label_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Ceding Commission</link:label>
    <link:label id="lab_skwd_DeferredCedingCommission_documentation_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Ceding Commission</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredCedingCommission" xlink:href="skwd-20260331.xsd#skwd_DeferredCedingCommission"/>
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    <link:label id="lab_us-gaap_RelatedPartyMember_019bdc32-ab60-7896-977c-f180fde50e3b_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party</link:label>
    <link:label id="lab_us-gaap_RelatedPartyMember_label_en-US" xlink:label="lab_us-gaap_RelatedPartyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RelatedPartyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyMember" xlink:to="lab_us-gaap_RelatedPartyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsMember_019bdc32-ac93-742c-a785-24b01d8873fd_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsMember" xlink:to="lab_us-gaap_EquityMethodInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock_019bdc32-ab60-7855-8a96-872f0ddf317b_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Components of Income Tax Expense</link:label>
    <link:label id="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Components of Income Tax Expense (Benefit) [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock"/>
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    <link:label id="lab_ecd_PeoMember_terseLabel_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO</link:label>
    <link:label id="lab_ecd_PeoMember_label_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO [Member]</link:label>
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    <link:label id="lab_us-gaap_RetainedEarningsMember_019bdc32-ac18-7520-b79e-33c6710f6619_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retained earnings:</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsMember_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retained Earnings [Member]</link:label>
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    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_019bdc32-ac19-7f8c-a54c-fcc8fecce9b3_totalLabel_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total paid</link:label>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
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    <link:label id="lab_us-gaap_IncomeTaxAuthorityAxis_019de310-8f59-7cac-a333-8d958f0265fe_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Axis]</link:label>
    <link:label id="lab_us-gaap_IncomeTaxAuthorityAxis_label_en-US" xlink:label="lab_us-gaap_IncomeTaxAuthorityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Jurisdiction [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxAuthorityAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxAuthorityAxis"/>
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    <link:label id="lab_us-gaap_InvestmentsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments, Fair Value Disclosure</link:label>
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    <link:label id="lab_srt_ProductsAndServicesDomain_019bdc32-ac18-747e-a9a0-e521a2e98c92_terseLabel_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:label id="lab_srt_ProductsAndServicesDomain_label_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductsAndServicesDomain" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_ProductsAndServicesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductsAndServicesDomain" xlink:to="lab_srt_ProductsAndServicesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetInvestmentIncome_019bdc32-ac19-73b9-a212-692ee776821e_terseLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_019bdc32-ac19-7dc8-be5f-196d2a949370_totalLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_label_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Investment Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetInvestmentIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetInvestmentIncome" xlink:to="lab_us-gaap_NetInvestmentIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_terseLabel_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement does not require Recovery</link:label>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_label_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Does Not Require Recovery [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_RestatementDoesNotRequireRecoveryTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:to="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable_019d776a-acd7-7391-8024-3c888abf91ac_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:to="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_019bdc32-ac18-7c86-9e4f-3de65e824aaa_terseLabel_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross realized gains</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_label_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Gains [Abstract]</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_documentation_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Gains</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossRealizedInvestmentGainsAbstract" xlink:href="skwd-20260331.xsd#skwd_GrossRealizedInvestmentGainsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossRealizedInvestmentGainsAbstract" xlink:to="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_019bdc32-ab60-7506-8657-6ae9e95f8978_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Realized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquitySecuritiesFvNiRealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_019d777b-2ed0-7bfd-b257-09e10c454746_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Preliminary Purchase Price Allocation</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired and Liability Assumed [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CityAreaCode_019bdc32-ab60-72da-ada7-95c7fa52ffec_terseLabel_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">City Area Code</link:label>
    <link:label id="lab_dei_CityAreaCode_label_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">City Area Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CityAreaCode" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_CityAreaCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CityAreaCode" xlink:to="lab_dei_CityAreaCode" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardTmgHowMnpiCnsdrdTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:to="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LoansReceivableMeasurementInput_019bdc32-ac18-7a5c-aaf3-01722fb8ff80_terseLabel_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loans receivable</link:label>
    <link:label id="lab_skwd_LoansReceivableMeasurementInput_label_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans Receivable, Measurement Input</link:label>
    <link:label id="lab_skwd_LoansReceivableMeasurementInput_documentation_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loans Receivable, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LoansReceivableMeasurementInput" xlink:href="skwd-20260331.xsd#skwd_LoansReceivableMeasurementInput"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LoansReceivableMeasurementInput" xlink:to="lab_skwd_LoansReceivableMeasurementInput" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_019bdc32-ac18-785f-b41c-a21a4cd777bf_totalLabel_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total incurred, net of reinsurance</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_label_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Net</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_documentation_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:href="skwd-20260331.xsd#skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:to="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_019dcf65-f294-7362-8f5c-68256729cd8e_terseLabel_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Corporate expenses</link:label>
    <link:label id="lab_us-gaap_GeneralAndAdministrativeExpense_label_en-US" xlink:label="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">General and Administrative Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeneralAndAdministrativeExpense" xlink:to="lab_us-gaap_GeneralAndAdministrativeExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_019bdc32-ac94-77af-b209-3973a5789183_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from investing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Investing Activity, Including Discontinued Operation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PvpTable_terseLabel_en-US" xlink:label="lab_ecd_PvpTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure</link:label>
    <link:label id="lab_ecd_PvpTable_label_en-US" xlink:label="lab_ecd_PvpTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTable" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PvpTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PvpTable" xlink:to="lab_ecd_PvpTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueHedgingMember_019bdc32-ac18-7311-907f-a0ac6b1d3fb0_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueHedgingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hedging</link:label>
    <link:label id="lab_us-gaap_FairValueHedgingMember_label_en-US" xlink:label="lab_us-gaap_FairValueHedgingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hedging [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueHedgingMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueHedgingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueHedgingMember" xlink:to="lab_us-gaap_FairValueHedgingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsAbstract_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transactions [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RelatedPartyTransactionsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionsAbstract" xlink:to="lab_us-gaap_RelatedPartyTransactionsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems_019de30f-4692-70ad-968f-2470737f7211_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation [Line Items]</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationLineItems"/>
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    <link:label id="lab_us-gaap_Goodwill_019bdc32-ac19-790b-a392-3c6f63df5918_netLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Goodwill, net balance</link:label>
    <link:label id="lab_us-gaap_Goodwill_019d779b-1e7c-774b-929e-8c6ca79458a9_terseLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
    <link:label id="lab_us-gaap_Goodwill_label_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Goodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Goodwill" xlink:to="lab_us-gaap_Goodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_019bdc32-ac94-70a8-a344-08de961faa15_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity securities, at fair value</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_019bdc32-ac94-796a-a15b-d49ab1970c72_verboseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:to="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019bdc32-ac18-7622-a33f-8670424a7367_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Current Year</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019bdc32-ac94-786e-8ec2-60c34b3efc33_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019bdc32-ac94-7963-944c-ead5f37bf310_totalLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net investment gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019bdc32-ac94-7bce-937e-441b7ef61f70_verboseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net investment gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GainLossOnInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestments" xlink:to="lab_us-gaap_GainLossOnInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_019bdc32-ab60-7266-9319-8086b6eb29fc_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Supplemental disclosure of cash flow information:</link:label>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_label_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Supplemental Cash Flow Information [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SupplementalCashFlowInformationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:to="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables_019d7783-28b6-795e-bfc5-464871c7ecf2_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums receivable, net</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Receivable, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss_019bdc32-ab5f-7684-8497-6faab7a410f1_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Accumulated impairment</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss_label_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Impaired, Accumulated Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GoodwillImpairedAccumulatedImpairmentLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:to="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_label_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OtherPerfMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_OtherPerfMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OtherPerfMeasureAmt" xlink:to="lab_ecd_OtherPerfMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_019bdc32-ac19-7d91-80b7-1e4633202bea_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasurementPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:to="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyDomain_019bdc32-ac94-7280-a394-9fce106c40bb_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party [Domain]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyDomain_label_en-US" xlink:label="lab_us-gaap_RelatedPartyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related and Nonrelated Parties [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RelatedPartyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyDomain" xlink:to="lab_us-gaap_RelatedPartyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_019bdc32-ac19-703d-9924-241d8fe0aa10_terseLabel_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II LP units</link:label>
    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_label_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II, L.P. [Member]</link:label>
    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_documentation_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II, L.P.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BrewerLaneVenturesFundIILPMember" xlink:href="skwd-20260331.xsd#skwd_BrewerLaneVenturesFundIILPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BrewerLaneVenturesFundIILPMember" xlink:to="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareReconciliationAbstract_019bdc32-ac94-731e-ab5b-bbc838a6e711_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted-average common shares outstanding</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareReconciliationAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share Reconciliation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareReconciliationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EarningsPerShareReconciliationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareReconciliationAbstract" xlink:to="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SkywardSpecialtySegmentMember_019dbfc9-c958-7742-af28-341ee38e688a_terseLabel_en-US" xlink:label="lab_skwd_SkywardSpecialtySegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Skyward Specialty Segment</link:label>
    <link:label id="lab_skwd_SkywardSpecialtySegmentMember_label_en-US" xlink:label="lab_skwd_SkywardSpecialtySegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Skyward Specialty Segment [Member]</link:label>
    <link:label id="lab_skwd_SkywardSpecialtySegmentMember_documentation_en-US" xlink:label="lab_skwd_SkywardSpecialtySegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Skyward Specialty Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SkywardSpecialtySegmentMember" xlink:href="skwd-20260331.xsd#skwd_SkywardSpecialtySegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SkywardSpecialtySegmentMember" xlink:to="lab_skwd_SkywardSpecialtySegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsAbstract_019bdc32-ac94-728d-a05f-9f51ad93f061_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments:</link:label>
    <link:label id="lab_us-gaap_InvestmentsAbstract_label_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InvestmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsAbstract" xlink:to="lab_us-gaap_InvestmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_019bdc32-ac19-7946-b265-46aa3f68a97e_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash used in investment activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash Provided by (Used in) Investing Activity, Including Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_019bdc32-ac18-7ab1-9d31-f62c6523a39f_terseLabel_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total investment income</link:label>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_label_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_documentation_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossInvestmentIncomeExpenseOperating" xlink:href="skwd-20260331.xsd#skwd_GrossInvestmentIncomeExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossInvestmentIncomeExpenseOperating" xlink:to="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table</link:label>
    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_label_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:to="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnderwritingIncomeNet_019bdc32-ac94-7c05-ab93-01cf204c9dd3_totalLabel_en-US" xlink:label="lab_skwd_UnderwritingIncomeNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Underwriting income</link:label>
    <link:label id="lab_skwd_UnderwritingIncomeNet_label_en-US" xlink:label="lab_skwd_UnderwritingIncomeNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting Income, Net</link:label>
    <link:label id="lab_skwd_UnderwritingIncomeNet_documentation_en-US" xlink:label="lab_skwd_UnderwritingIncomeNet" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Underwriting Income, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingIncomeNet" xlink:href="skwd-20260331.xsd#skwd_UnderwritingIncomeNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnderwritingIncomeNet" xlink:to="lab_skwd_UnderwritingIncomeNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestPaidNet_019bdc32-ac19-737c-ab55-a1e00505db56_terseLabel_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash paid for interest</link:label>
    <link:label id="lab_us-gaap_InterestPaidNet_label_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Interest Paid, Excluding Capitalized Interest, Operating Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InterestPaidNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestPaidNet" xlink:to="lab_us-gaap_InterestPaidNet" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalYearFocus_019bdc32-ac19-7ba2-9fb7-05f795e35963_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalYearFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalYearFocus" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_DocumentFiscalYearFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalYearFocus" xlink:to="lab_dei_DocumentFiscalYearFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_019bdc32-ac94-7da5-b29d-831612b28bf0_verboseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Effects of Reinsurance</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effects of Reinsurance [Table Text Block]</link:label>
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    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Basis of Accounting, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BasisOfAccountingPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_019bdc32-ac94-76be-9b87-bfa86747c8ba_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective tax rate</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_019bdc32-ab60-7791-830a-bc8dea7f70c5_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Axis]</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:type="arc" order="1"/>
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    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_019bdc32-ac18-723c-a83b-908bee143798_totalLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total underwriting, acquisition and insurance expenses</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_label_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense And Other Cost And Expense, Operating</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_documentation_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense And Other Cost And Expense, Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:href="skwd-20260331.xsd#skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:to="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_019bdc32-ac94-7f6a-b04a-468936b28bae_terseLabel_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reported Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CarryingReportedAmountFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:to="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityAbstract_019bdc32-ac94-7616-8c7f-454958551000_terseLabel_en-US" xlink:label="lab_us-gaap_EquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_EquityAbstract_label_en-US" xlink:label="lab_us-gaap_EquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityAbstract" xlink:to="lab_us-gaap_EquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RealizedInvestmentGains_019bdc32-ac94-74ae-ba6e-b9e4590b9a78_totalLabel_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_RealizedInvestmentGains_label_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Realized Investment Gains</link:label>
    <link:label id="lab_skwd_RealizedInvestmentGains_documentation_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Realized Investment Gains</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RealizedInvestmentGains" xlink:href="skwd-20260331.xsd#skwd_RealizedInvestmentGains"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RealizedInvestmentGains" xlink:to="lab_skwd_RealizedInvestmentGains" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_019bdc32-ac19-74df-8d22-3cbaa68ff5e6_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in direct and indirect loans</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_label_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments To Acquire) Equity Method Investments</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_documentation_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments To Acquire) Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:href="skwd-20260331.xsd#skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:to="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_019bdc32-ab5f-7ee4-a36e-92f308be26ab_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earned</link:label>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_label_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract"/>
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    <link:label id="lab_us-gaap_SegmentReportingDisclosureTextBlock_019bdc32-ac19-7af9-8365-3d66d9e43eee_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments</link:label>
    <link:label id="lab_us-gaap_SegmentReportingDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SegmentReportingDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingDisclosureTextBlock" xlink:to="lab_us-gaap_SegmentReportingDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CoverHolderRelationshipsMember_019d77ac-024e-7b21-8fb0-4de88ddecc45_terseLabel_en-US" xlink:label="lab_skwd_CoverHolderRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cover holder relationships</link:label>
    <link:label id="lab_skwd_CoverHolderRelationshipsMember_label_en-US" xlink:label="lab_skwd_CoverHolderRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cover Holder Relationships [Member]</link:label>
    <link:label id="lab_skwd_CoverHolderRelationshipsMember_documentation_en-US" xlink:label="lab_skwd_CoverHolderRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Cover Holder Relationships</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CoverHolderRelationshipsMember" xlink:href="skwd-20260331.xsd#skwd_CoverHolderRelationshipsMember"/>
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    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_019bdc32-ac94-74a2-a8a7-9e04e8a693cd_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems"/>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_019bdc32-ac18-7af8-bbb1-23dadd0ec30a_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="skwd-20260331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger"/>
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    <link:label id="lab_us-gaap_TrademarksMember_019bdc32-ac18-7316-b8ca-47e3fc85add9_terseLabel_en-US" xlink:label="lab_us-gaap_TrademarksMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trademarks</link:label>
    <link:label id="lab_us-gaap_TrademarksMember_label_en-US" xlink:label="lab_us-gaap_TrademarksMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trademarks [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TrademarksMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_TrademarksMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TrademarksMember" xlink:to="lab_us-gaap_TrademarksMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_019bdc32-ab5f-7d0e-847c-a8acd2463893_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInStockholdersEquityRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:to="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract_019bdc32-ac18-7e81-93ea-ffea445915af_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available for sale, gross unrealized losses</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Accumulated Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems_019bdc32-ac19-7259-910f-dab3511dccac_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets [Line Items]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Total Shareholder Return</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Total Shareholder Return [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_019bdc32-ac19-7524-9d90-0286d4a2ae04_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Recurring and Nonrecurring [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Recurring and Nonrecurring [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable"/>
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    <link:label id="lab_srt_WeightedAverageMember_019bdc32-ab5f-72ff-9c1c-4baf6e0d9e07_terseLabel_en-US" xlink:label="lab_srt_WeightedAverageMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted average</link:label>
    <link:label id="lab_srt_WeightedAverageMember_label_en-US" xlink:label="lab_srt_WeightedAverageMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_WeightedAverageMember" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_WeightedAverageMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_WeightedAverageMember" xlink:to="lab_srt_WeightedAverageMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_019bdc32-ac18-71a0-9b5a-e8e69934c254_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Amortization</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_019bdc32-ac18-7b65-bf36-b3cbf4ec3233_verboseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amortization of intangible assets</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amortization of Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AmortizationOfIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:to="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RISCOMMember_019bdc32-ac94-7a7e-8f99-652e29fd87e9_terseLabel_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">RISCOM</link:label>
    <link:label id="lab_skwd_RISCOMMember_label_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">RISCOM [Member]</link:label>
    <link:label id="lab_skwd_RISCOMMember_documentation_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">RISCOM</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RISCOMMember" xlink:href="skwd-20260331.xsd#skwd_RISCOMMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RISCOMMember" xlink:to="lab_skwd_RISCOMMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_019bdc32-ac94-7c01-a01d-d84971e5fdd0_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax assets</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Income Tax Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredIncomeTaxAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxAssetsNet" xlink:to="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_019bdc32-ac19-7673-828d-4b20438c8017_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss)</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss) [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireProductiveAssets_019e08bd-1a8c-7a86-b024-318ed10efb10_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireProductiveAssets" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from the sales of (payments for the purchase of) property and equipment</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireProductiveAssets_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireProductiveAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Productive Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireProductiveAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquireProductiveAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireProductiveAssets" xlink:to="lab_us-gaap_PaymentsToAcquireProductiveAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_019bdc32-ac19-7823-bffb-79f5071d5daa_terseLabel_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Spread Adjustment</link:label>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_label_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Spread Adjustment [Member]</link:label>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_documentation_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Credit Spread Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditSpreadAdjustmentMember" xlink:href="skwd-20260331.xsd#skwd_CreditSpreadAdjustmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CreditSpreadAdjustmentMember" xlink:to="lab_skwd_CreditSpreadAdjustmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_019bdc32-ab5f-74c1-bcfd-3ed219f4aaeb_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:href="skwd-20260331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months"/>
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    <link:label id="lab_skwd_ProfitCommissionPercentage_019d77d0-d803-7edd-beeb-d196d1e9b3c8_terseLabel_en-US" xlink:label="lab_skwd_ProfitCommissionPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Profit commission (in percent)</link:label>
    <link:label id="lab_skwd_ProfitCommissionPercentage_label_en-US" xlink:label="lab_skwd_ProfitCommissionPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Profit Commission Percentage</link:label>
    <link:label id="lab_skwd_ProfitCommissionPercentage_documentation_en-US" xlink:label="lab_skwd_ProfitCommissionPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Profit Commission Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProfitCommissionPercentage" xlink:href="skwd-20260331.xsd#skwd_ProfitCommissionPercentage"/>
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    <link:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_019bdc32-ac18-7512-95eb-f237ce1123d7_terseLabel_en-US" xlink:label="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Residential mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Residential Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ResidentialMortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_019bdc32-ac19-7051-aed1-3ddaa34aa659_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Funds held for others</link:label>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_label_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Funds Held under Reinsurance Agreements, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:to="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_019bdc32-ab5f-767b-ae50-59683e62461c_terseLabel_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility [Member]</link:label>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_label_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevolvingCreditFacilityMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RevolvingCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevolvingCreditFacilityMember" xlink:to="lab_us-gaap_RevolvingCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_019bdc32-ac19-7749-9754-6ad37200cd84_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Direct premiums</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Direct Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DirectPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsWritten" xlink:to="lab_us-gaap_DirectPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrDuration_terseLabel_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arrangement Duration</link:label>
    <link:label id="lab_ecd_TrdArrDuration_label_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Duration</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrDuration" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TrdArrDuration"/>
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    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_019bdc32-ac93-72e2-86e5-3396c246d3af_terseLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Debt Securities, Trading, and Equity Securities, FV-NI</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_label_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI [Table Text Block]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:to="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract_019bdc32-ac19-723c-be67-4021c237cb2f_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Held-to-maturity, fair value</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_019bdc32-ac94-7198-903c-83a066ff1283_terseLabel_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementBusinessSegmentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StatementBusinessSegmentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementBusinessSegmentsAxis" xlink:to="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_LocalPhoneNumber_019bdc32-ab5f-706f-ba13-e88a5ced549c_terseLabel_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Local Phone Number</link:label>
    <link:label id="lab_dei_LocalPhoneNumber_label_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Local Phone Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LocalPhoneNumber" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_LocalPhoneNumber"/>
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    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure</link:label>
    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_label_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Additional402vDisclosureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_Additional402vDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Additional402vDisclosureTextBlock" xlink:to="lab_ecd_Additional402vDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_019bdc32-ac18-739c-9e95-454c410aa2f3_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SUA commission revenue</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_label_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Commission Revenue [Member]</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_documentation_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managing General Insurance Agent And Broker, Commission Revenue</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:href="skwd-20260331.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:to="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GlobalAndPropertyMember_019bdc32-ac18-7fc8-92c9-79fb6270a7f2_terseLabel_en-US" xlink:label="lab_skwd_GlobalAndPropertyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Global Property</link:label>
    <link:label id="lab_skwd_GlobalAndPropertyMember_label_en-US" xlink:label="lab_skwd_GlobalAndPropertyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Global and Property [Member]</link:label>
    <link:label id="lab_skwd_GlobalAndPropertyMember_documentation_en-US" xlink:label="lab_skwd_GlobalAndPropertyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Global and Property</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GlobalAndPropertyMember" xlink:href="skwd-20260331.xsd#skwd_GlobalAndPropertyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GlobalAndPropertyMember" xlink:to="lab_skwd_GlobalAndPropertyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_019d7788-ff4c-7e91-8c81-818eae7e6a1a_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible assets, excluding goodwill, net</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_019d77b0-034d-7e3a-aa93-f034a4b4bc25_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Excluding Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_019d7781-5591-7679-958a-d9e1c81abbca_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash and cash equivalents</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Cash and Cash Equivalent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents"/>
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    <link:label id="lab_us-gaap_AssetsAbstract_019bdc32-ab5f-71b5-8f45-fefa315c1b44_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assets</link:label>
    <link:label id="lab_us-gaap_AssetsAbstract_label_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsAbstract" xlink:to="lab_us-gaap_AssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityAxis_019bdc32-ac19-7772-be41-e93901b4f27c_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityAxis_label_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CreditFacilityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityAxis" xlink:to="lab_us-gaap_CreditFacilityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NumberOfMortgageLoansNotProducingIncome_019bdc32-ac19-76fa-8e2c-e4e232b41553_terseLabel_en-US" xlink:label="lab_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans not producing income</link:label>
    <link:label id="lab_skwd_NumberOfMortgageLoansNotProducingIncome_label_en-US" xlink:label="lab_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number Of Mortgage Loans Not Producing Income</link:label>
    <link:label id="lab_skwd_NumberOfMortgageLoansNotProducingIncome_documentation_en-US" xlink:label="lab_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number Of Mortgage Loans Not Producing Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:href="skwd-20260331.xsd#skwd_NumberOfMortgageLoansNotProducingIncome"/>
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    <link:label id="lab_ecd_UndrlygSecurityMktPriceChngPct_terseLabel_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change</link:label>
    <link:label id="lab_ecd_UndrlygSecurityMktPriceChngPct_label_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_UndrlygSecurityMktPriceChngPct"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:to="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_019bdc32-ac18-72d4-9b34-5e2f59e82530_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentAxis" xlink:to="lab_us-gaap_DebtInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_019bdc32-ab5f-7e2b-8f54-a88e86b1cb53_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurements</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueDisclosuresTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:to="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionLineItems_019d776a-acd7-791a-a983-5d8bcd719958_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Line Items]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionLineItems_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessAcquisitionLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionLineItems" xlink:to="lab_us-gaap_BusinessAcquisitionLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityDomain_019bdc32-ab60-7aac-a804-67dbf0c7dcf4_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityDomain_label_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CreditFacilityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityDomain" xlink:to="lab_us-gaap_CreditFacilityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockValueAcquiredCostMethod_019dcf77-1881-7a89-bf38-ae16660f10d5_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockValueAcquiredCostMethod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock acquired</link:label>
    <link:label id="lab_us-gaap_TreasuryStockValueAcquiredCostMethod_label_en-US" xlink:label="lab_us-gaap_TreasuryStockValueAcquiredCostMethod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Value, Acquired, Cost Method</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockValueAcquiredCostMethod" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_TreasuryStockValueAcquiredCostMethod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockValueAcquiredCostMethod" xlink:to="lab_us-gaap_TreasuryStockValueAcquiredCostMethod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceCommissions_019bdc32-ac18-7d66-9f58-1bb822a2eb7d_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commissions</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissions_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Commissions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissions" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InsuranceCommissions"/>
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    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate, Stated Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentInterestRateStatedPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:to="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_019bdc32-ac18-7dd9-9732-cc849fa55c47_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_label_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:href="https://xbrl.fasb.org/srt/2025/elts/srt-2025.xsd#srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:to="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_019bdc32-ac19-7333-8458-4f1d29f25ed2_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale:</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value to Amortized Cost, after Allowance for Credit Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_019bdc32-ac19-789c-959c-713733b6b27e_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other long-term investments</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLongTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherLongTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLongTermInvestments" xlink:to="lab_us-gaap_OtherLongTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DerivativeFairValueOfDerivativeAsset_019bdc32-ac19-7100-b05d-544e661bc9f9_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeFairValueOfDerivativeAsset" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative assets, fair value</link:label>
    <link:label id="lab_us-gaap_DerivativeFairValueOfDerivativeAsset_label_en-US" xlink:label="lab_us-gaap_DerivativeFairValueOfDerivativeAsset" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Asset, Subject to Master Netting Arrangement, before Offset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeFairValueOfDerivativeAsset" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DerivativeFairValueOfDerivativeAsset"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeFairValueOfDerivativeAsset" xlink:to="lab_us-gaap_DerivativeFairValueOfDerivativeAsset" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityRegistrantName_019bdc32-ab5f-78ec-96e2-49f8f4c84f62_terseLabel_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:label id="lab_dei_EntityRegistrantName_label_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityRegistrantName" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_EntityRegistrantName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityRegistrantName" xlink:to="lab_dei_EntityRegistrantName" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue_019bdc32-ac94-734b-8bce-45a3bba28e9e_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Percentage of property appraisal value</link:label>
    <link:label id="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue_label_en-US" xlink:label="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans on Real Estate, Principal Amount, Percentage of Property Appraisal Value</link:label>
    <link:label id="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue_documentation_en-US" xlink:label="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage Loans on Real Estate, Principal Amount, Percentage of Property Appraisal Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:href="skwd-20260331.xsd#skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:to="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method</link:label>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_label_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_StkPrcOrTsrEstimationMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:to="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MunicipalBondsMember_019bdc32-ab5f-7931-a383-69b628a378ae_terseLabel_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Municipal securities</link:label>
    <link:label id="lab_us-gaap_MunicipalBondsMember_label_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Municipal Bonds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MunicipalBondsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_MunicipalBondsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MunicipalBondsMember" xlink:to="lab_us-gaap_MunicipalBondsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_Syndicate1971DigitalEconomyMember_019d47d2-8790-7613-ab51-50ddfaf8582f_terseLabel_en-US" xlink:label="lab_skwd_Syndicate1971DigitalEconomyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate 1971</link:label>
    <link:label id="lab_skwd_Syndicate1971DigitalEconomyMember_label_en-US" xlink:label="lab_skwd_Syndicate1971DigitalEconomyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate 1971 - Digital Economy [Member]</link:label>
    <link:label id="lab_skwd_Syndicate1971DigitalEconomyMember_documentation_en-US" xlink:label="lab_skwd_Syndicate1971DigitalEconomyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate 1971 - Digital Economy</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_Syndicate1971DigitalEconomyMember" xlink:href="skwd-20260331.xsd#skwd_Syndicate1971DigitalEconomyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_Syndicate1971DigitalEconomyMember" xlink:to="lab_skwd_Syndicate1971DigitalEconomyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_019bdc32-ac19-72fa-a4fd-c2107b016aea_totalLabel_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssetsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsFairValueDisclosure" xlink:to="lab_us-gaap_AssetsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions_019bdc32-ab5f-7cb4-956e-838e3fa2488b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of securities</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Number of Positions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JVMFundsLLCMember_019bdc32-ab5f-770b-854b-7a87be2b7c7b_terseLabel_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">JVM Funds LLC</link:label>
    <link:label id="lab_skwd_JVMFundsLLCMember_label_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">JVM Funds LLC [Member]</link:label>
    <link:label id="lab_skwd_JVMFundsLLCMember_documentation_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">JVM Funds LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JVMFundsLLCMember" xlink:href="skwd-20260331.xsd#skwd_JVMFundsLLCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JVMFundsLLCMember" xlink:to="lab_skwd_JVMFundsLLCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NumberOfOperatingSegments_019bdc32-ac18-7369-bc27-a8341561c26a_terseLabel_en-US" xlink:label="lab_us-gaap_NumberOfOperatingSegments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of operating segments</link:label>
    <link:label id="lab_us-gaap_NumberOfOperatingSegments_label_en-US" xlink:label="lab_us-gaap_NumberOfOperatingSegments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Operating Segments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NumberOfOperatingSegments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NumberOfOperatingSegments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NumberOfOperatingSegments" xlink:to="lab_us-gaap_NumberOfOperatingSegments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentInterestRateFloor_019d20c6-513b-708c-bed6-02509917edc2_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentInterestRateFloor" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, interest rate floor</link:label>
    <link:label id="lab_skwd_DebtInstrumentInterestRateFloor_label_en-US" xlink:label="lab_skwd_DebtInstrumentInterestRateFloor" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate Floor</link:label>
    <link:label id="lab_skwd_DebtInstrumentInterestRateFloor_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentInterestRateFloor" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate Floor</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentInterestRateFloor" xlink:href="skwd-20260331.xsd#skwd_DebtInstrumentInterestRateFloor"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentInterestRateFloor" xlink:to="lab_skwd_DebtInstrumentInterestRateFloor" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi_019bdc32-ac18-77f0-9828-312e2233e535_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of equity securities</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquireEquitySecuritiesFvNi"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:to="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_019bdc32-ac18-7e7d-a282-c3eddd3350a3_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party [Axis]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related and Nonrelated Parties [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RelatedPartyTransactionsByRelatedPartyAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:to="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MaterialReconcilingItemsMember_019bdc32-ac18-74a8-9cb2-b19a259a7055_terseLabel_en-US" xlink:label="lab_us-gaap_MaterialReconcilingItemsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Corporate Nonsegment</link:label>
    <link:label id="lab_us-gaap_MaterialReconcilingItemsMember_label_en-US" xlink:label="lab_us-gaap_MaterialReconcilingItemsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting, Reconciling Item, Excluding Corporate Nonsegment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MaterialReconcilingItemsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_MaterialReconcilingItemsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MaterialReconcilingItemsMember" xlink:to="lab_us-gaap_MaterialReconcilingItemsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue_019bdc32-ac18-74d7-b7f8-f10f2d539b3a_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDateAxis_terseLabel_en-US" xlink:label="lab_ecd_RestatementDateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement Determination Date:</link:label>
    <link:label id="lab_ecd_RestatementDateAxis_label_en-US" xlink:label="lab_ecd_RestatementDateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Determination Date [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDateAxis" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_RestatementDateAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDateAxis" xlink:to="lab_ecd_RestatementDateAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_019bdc32-ac19-7f48-9684-d51dd427ad65_verboseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Issuance of common stock</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shares Issued, Value, Share-Based Payment Arrangement, after Forfeiture</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CreditAndSuretyMember_019d4796-0e0c-7a62-acdf-1a77cf46c50c_verboseLabel_en-US" xlink:label="lab_skwd_CreditAndSuretyMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Credit &amp; Surety</link:label>
    <link:label id="lab_skwd_CreditAndSuretyMember_019bdc32-ab60-7bfe-9a5e-d6080a7dbaaa_terseLabel_en-US" xlink:label="lab_skwd_CreditAndSuretyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit &amp; Surety</link:label>
    <link:label id="lab_skwd_CreditAndSuretyMember_label_en-US" xlink:label="lab_skwd_CreditAndSuretyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit And Surety [Member]</link:label>
    <link:label id="lab_skwd_CreditAndSuretyMember_documentation_en-US" xlink:label="lab_skwd_CreditAndSuretyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Credit And Surety</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditAndSuretyMember" xlink:href="skwd-20260331.xsd#skwd_CreditAndSuretyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CreditAndSuretyMember" xlink:to="lab_skwd_CreditAndSuretyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReportingUnitAxis_019bdc32-ac94-7c71-a382-75c6c2b6e226_terseLabel_en-US" xlink:label="lab_us-gaap_ReportingUnitAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reporting Unit [Axis]</link:label>
    <link:label id="lab_us-gaap_ReportingUnitAxis_label_en-US" xlink:label="lab_us-gaap_ReportingUnitAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reporting Unit [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReportingUnitAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReportingUnitAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReportingUnitAxis" xlink:to="lab_us-gaap_ReportingUnitAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract_019d7797-755f-7262-9edc-8552283391e3_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities assumed</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrIndName_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_TrdArrIndName_label_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndName" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_TrdArrIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndName" xlink:to="lab_ecd_TrdArrIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_019bdc32-ac94-7ceb-90c2-fb06939dce47_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Face amount</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Face Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentFaceAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentFaceAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentFaceAmount" xlink:to="lab_us-gaap_DebtInstrumentFaceAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019bdc32-ac18-7a9e-88a9-795e997618c5_negatedTerseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="skwd-20260331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_019d7775-387b-7532-aca5-105b9cc13cdc_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consideration of Skyward Specialty Insurance Group, Inc. issued common stock</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Consideration Transferred, Equity Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:to="lab_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockMember_019bdc32-ac93-7967-ad23-1d50da74279f_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred stocks</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_label_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PreferredStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockMember" xlink:to="lab_us-gaap_PreferredStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AccidentAndHealthMember_019bdc32-ac18-7c8e-9fc3-597a12c20b46_terseLabel_en-US" xlink:label="lab_skwd_AccidentAndHealthMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident and Health</link:label>
    <link:label id="lab_skwd_AccidentAndHealthMember_label_en-US" xlink:label="lab_skwd_AccidentAndHealthMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accident and Health [Member]</link:label>
    <link:label id="lab_skwd_AccidentAndHealthMember_documentation_en-US" xlink:label="lab_skwd_AccidentAndHealthMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Accident and Health</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AccidentAndHealthMember" xlink:href="skwd-20260331.xsd#skwd_AccidentAndHealthMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AccidentAndHealthMember" xlink:to="lab_skwd_AccidentAndHealthMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscIndName_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscIndName_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscIndName" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardsCloseToMnpiDiscIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscIndName" xlink:to="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtErrCompNotYetDeterminedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined</link:label>
    <link:label id="lab_ecd_AggtErrCompNotYetDeterminedTextBlock_label_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AggtErrCompNotYetDeterminedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:to="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TermLoanDueAugust2029Member_019bdc32-ab60-7e16-b030-3326a3830651_terseLabel_en-US" xlink:label="lab_skwd_TermLoanDueAugust2029Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">FHLB Loan</link:label>
    <link:label id="lab_skwd_TermLoanDueAugust2029Member_label_en-US" xlink:label="lab_skwd_TermLoanDueAugust2029Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Term Loan Due August 2029 [Member]</link:label>
    <link:label id="lab_skwd_TermLoanDueAugust2029Member_documentation_en-US" xlink:label="lab_skwd_TermLoanDueAugust2029Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Term Loan Due August 2029</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TermLoanDueAugust2029Member" xlink:href="skwd-20260331.xsd#skwd_TermLoanDueAugust2029Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TermLoanDueAugust2029Member" xlink:to="lab_skwd_TermLoanDueAugust2029Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansUnrealizedGainLoss_019bdc32-ac94-75f5-9d6b-6897b5abf52c_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_skwd_MortgageLoansUnrealizedGainLoss_label_en-US" xlink:label="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans, Unrealized Gain (Loss)</link:label>
    <link:label id="lab_skwd_MortgageLoansUnrealizedGainLoss_documentation_en-US" xlink:label="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage Loans, Unrealized Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansUnrealizedGainLoss" xlink:href="skwd-20260331.xsd#skwd_MortgageLoansUnrealizedGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MortgageLoansUnrealizedGainLoss" xlink:to="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PlatformPartnerSyndicatesMember_019dcf95-2556-7eaf-8ea4-e0813514f212_terseLabel_en-US" xlink:label="lab_skwd_PlatformPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Partner Syndicates</link:label>
    <link:label id="lab_skwd_PlatformPartnerSyndicatesMember_label_en-US" xlink:label="lab_skwd_PlatformPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Platform Partner Syndicates [Member]</link:label>
    <link:label id="lab_skwd_PlatformPartnerSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_PlatformPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Platform Partner Syndicates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PlatformPartnerSyndicatesMember" xlink:href="skwd-20260331.xsd#skwd_PlatformPartnerSyndicatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PlatformPartnerSyndicatesMember" xlink:to="lab_skwd_PlatformPartnerSyndicatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockValue_019bdc32-ac18-7f83-b3a8-1fa9013007d3_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock, at cost, 185,022 and 0 shares, respectively</link:label>
    <link:label id="lab_us-gaap_TreasuryStockValue_label_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_TreasuryStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockValue" xlink:to="lab_us-gaap_TreasuryStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignCountryMember_019de310-c261-775e-b462-a13c23b3332f_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignCountryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign Tax Jurisdiction</link:label>
    <link:label id="lab_us-gaap_ForeignCountryMember_label_en-US" xlink:label="lab_us-gaap_ForeignCountryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Foreign Tax Jurisdiction [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignCountryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ForeignCountryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ForeignCountryMember" xlink:to="lab_us-gaap_ForeignCountryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentDomain_019bdc32-ac94-7f77-91c6-146582b84c4e_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:label id="lab_us-gaap_SegmentDomain_label_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SegmentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentDomain" xlink:to="lab_us-gaap_SegmentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagedSyndicatesMember_019d77cc-788e-7d69-aefa-c43b8d75cdba_terseLabel_en-US" xlink:label="lab_skwd_ManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Managed Syndicates</link:label>
    <link:label id="lab_skwd_ManagedSyndicatesMember_label_en-US" xlink:label="lab_skwd_ManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Managed Syndicates [Member]</link:label>
    <link:label id="lab_skwd_ManagedSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_ManagedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Managed Syndicates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagedSyndicatesMember" xlink:href="skwd-20260331.xsd#skwd_ManagedSyndicatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagedSyndicatesMember" xlink:to="lab_skwd_ManagedSyndicatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_019bdc32-ac18-7256-b0c8-d18d004455e4_terseLabel_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Available-For-Sale</link:label>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_label_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FixedMaturitiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FixedMaturitiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FixedMaturitiesMember" xlink:to="lab_us-gaap_FixedMaturitiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_019bdc32-ac18-7022-bf21-d1558696295b_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:to="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_019bdc32-ab5f-7eba-a642-977c350d566a_terseLabel_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retail</link:label>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retail Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Retail Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RetailPortfolioSegmentMember" xlink:href="skwd-20260331.xsd#skwd_RetailPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RetailPortfolioSegmentMember" xlink:to="lab_skwd_RetailPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_019bdc32-ab60-7b07-a5fe-b93112915485_terseLabel_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arena Special Opportunities Fund, LP units</link:label>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_label_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Arena Special Opportunities Fund, LP [Member]</link:label>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_documentation_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Arena Special Opportunities Fund, LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:href="skwd-20260331.xsd#skwd_ArenaSpecialOpportunitiesFundLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:to="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_019bdc32-ab60-7b32-9c33-97417256d84b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubordinatedDebt_019bdc32-ac19-7476-b079-8fd05724302e_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
    <link:label id="lab_us-gaap_SubordinatedDebt_label_en-US" xlink:label="lab_us-gaap_SubordinatedDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subordinated Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubordinatedDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SubordinatedDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubordinatedDebt" xlink:to="lab_us-gaap_SubordinatedDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromStockPlans_019df2c5-3ff1-7db1-acd9-41a3ced1625e_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromStockPlans" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from issuance of common stock</link:label>
    <link:label id="lab_us-gaap_ProceedsFromStockPlans_label_en-US" xlink:label="lab_us-gaap_ProceedsFromStockPlans" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Stock Plans</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockPlans" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromStockPlans"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromStockPlans" xlink:to="lab_us-gaap_ProceedsFromStockPlans" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_019d779d-bef8-7517-93c9-43764f576f5e_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities assumed</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubordinatedDebtMember_019bdc32-ac18-78f7-b832-0f8ede3fccd1_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
    <link:label id="lab_us-gaap_SubordinatedDebtMember_label_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subordinated Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubordinatedDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SubordinatedDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubordinatedDebtMember" xlink:to="lab_us-gaap_SubordinatedDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllExecutiveCategoriesMember_terseLabel_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Executive Categories</link:label>
    <link:label id="lab_ecd_AllExecutiveCategoriesMember_label_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Executive Categories [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllExecutiveCategoriesMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AllExecutiveCategoriesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllExecutiveCategoriesMember" xlink:to="lab_ecd_AllExecutiveCategoriesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019bdc32-ac19-799f-9587-6e7205a83b98_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_019bdc32-ac94-75e3-8aa6-2a41d4afa847_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization of policy acquisition costs</link:label>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockValue_019bdc32-ac18-7677-baf0-47f03ae74f36_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, $0.01 par value, 500,000,000 shares authorized, 44,728,087 shares issued and 44,543,065 shares outstanding at March&#160;31, 2026; 40,511,222 shares issued and outstanding at December&#160;31, 2025</link:label>
    <link:label id="lab_us-gaap_CommonStockValue_label_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Value, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommonStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockValue" xlink:to="lab_us-gaap_CommonStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019bdc32-ac18-7bed-97d2-81dd89f409c5_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net earned premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019bdc32-ac18-7078-a3a4-184b42ad10e4_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_019bdc32-ac18-7d9d-a358-3fbd9b594cb2_verboseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net earned premium</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_label_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PremiumsEarnedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsEarnedNet" xlink:to="lab_us-gaap_PremiumsEarnedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable_019bdc32-ac94-760b-ad51-f4ef5e19641f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_VariableInterestEntityAbstract_019bdc32-ac19-73d9-adba-f92b89c2348d_terseLabel_en-US" xlink:label="lab_skwd_VariableInterestEntityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Abstract]</link:label>
    <link:label id="lab_skwd_VariableInterestEntityAbstract_label_en-US" xlink:label="lab_skwd_VariableInterestEntityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity [Abstract]</link:label>
    <link:label id="lab_skwd_VariableInterestEntityAbstract_documentation_en-US" xlink:label="lab_skwd_VariableInterestEntityAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Variable Interest Entity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_VariableInterestEntityAbstract" xlink:href="skwd-20260331.xsd#skwd_VariableInterestEntityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_VariableInterestEntityAbstract" xlink:to="lab_skwd_VariableInterestEntityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_019bdc32-ac19-7c80-b814-1147e8e6f54b_terseLabel_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II LP</link:label>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_label_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Brewer Lane Venture Fund II LP [Member]</link:label>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_documentation_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Brewer Lane Venture Fund II LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BrewerLaneVentureFundIILPMember" xlink:href="skwd-20260331.xsd#skwd_BrewerLaneVentureFundIILPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BrewerLaneVentureFundIILPMember" xlink:to="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles_019d77af-a07b-740e-bc51-a9faff747a14_verboseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Estimated fair value, finite-lived</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Finite-Lived</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember_019bdc32-ac18-7ac9-9a57-3439b8ef690f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measured at Net Asset Value Per Share</link:label>
    <link:label id="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember_label_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measured at Net Asset Value Per Share [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:to="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_019bdc32-ac18-702e-8644-079561e48d76_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Business Combination [Axis]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessAcquisitionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionAxis" xlink:to="lab_us-gaap_BusinessAcquisitionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_019bdc32-ac18-7bc1-8462-b646c74046c4_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Investment Income</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InvestmentIncomeTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeTextBlock" xlink:to="lab_us-gaap_InvestmentIncomeTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_019bdc32-ac19-78f7-867b-80ad7b9d645e_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ownership %</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Ownership Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestmentOwnershipPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:to="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount_019bdc32-ab5f-767b-a69f-1d943432e318_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans in foreclosure</link:label>
    <link:label id="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount_label_en-US" xlink:label="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans in Process of Foreclosure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_MortgageLoansInProcessOfForeclosureAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:to="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_019bdc32-ab60-7037-b8e1-058f411f9e92_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermInvestmentsMember" xlink:to="lab_us-gaap_ShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_019bdc32-ab60-7117-98e7-f426acc05d60_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded losses and LAE incurred</link:label>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_label_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Policyholder Benefits and Claims Incurred, Ceded</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:to="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_label_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoActuallyPaidCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_PeoActuallyPaidCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoActuallyPaidCompAmt" xlink:to="lab_ecd_PeoActuallyPaidCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtTerm_019bdc32-ac18-7658-a69a-351181f1e803_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt term</link:label>
    <link:label id="lab_us-gaap_LongTermDebtTerm_label_en-US" xlink:label="lab_us-gaap_LongTermDebtTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtTerm" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongTermDebtTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtTerm" xlink:to="lab_us-gaap_LongTermDebtTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_019bdc32-ac94-75a2-bb26-517d923579c8_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerAbstract_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RevenueFromContractWithCustomerAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HedgingDesignationAxis_019bdc32-ac18-7536-bfd9-555852331a0c_terseLabel_en-US" xlink:label="lab_us-gaap_HedgingDesignationAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hedging Designation [Axis]</link:label>
    <link:label id="lab_us-gaap_HedgingDesignationAxis_label_en-US" xlink:label="lab_us-gaap_HedgingDesignationAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hedging Designation [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HedgingDesignationAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HedgingDesignationAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HedgingDesignationAxis" xlink:to="lab_us-gaap_HedgingDesignationAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities_019d7796-9c73-73c1-92f0-76efd79c461c_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Deferred Tax Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities"/>
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    <link:label id="lab_skwd_TermLoanFacilityMember_019d203d-969f-72c3-8fe5-e838c07a94e3_terseLabel_en-US" xlink:label="lab_skwd_TermLoanFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Term Loan Facility, net of debt issuance costs</link:label>
    <link:label id="lab_skwd_TermLoanFacilityMember_label_en-US" xlink:label="lab_skwd_TermLoanFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Term Loan Facility [Member]</link:label>
    <link:label id="lab_skwd_TermLoanFacilityMember_documentation_en-US" xlink:label="lab_skwd_TermLoanFacilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Term Loan Facility</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TermLoanFacilityMember" xlink:href="skwd-20260331.xsd#skwd_TermLoanFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TermLoanFacilityMember" xlink:to="lab_skwd_TermLoanFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_019bdc32-ac19-7174-ab20-7076faedb7d0_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Losses and Loss Adjustment Expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock"/>
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    <link:label id="lab_skwd_NotesPayableMember_019bdc32-ac18-7bce-b76a-824ad5727986_terseLabel_en-US" xlink:label="lab_skwd_NotesPayableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notes payable</link:label>
    <link:label id="lab_skwd_NotesPayableMember_label_en-US" xlink:label="lab_skwd_NotesPayableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Payable [Member]</link:label>
    <link:label id="lab_skwd_NotesPayableMember_documentation_en-US" xlink:label="lab_skwd_NotesPayableMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Notes Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NotesPayableMember" xlink:href="skwd-20260331.xsd#skwd_NotesPayableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NotesPayableMember" xlink:to="lab_skwd_NotesPayableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_019bdc32-ab5f-76b7-af8a-6ec0a40b25a1_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllIndividualsMember_terseLabel_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Individuals</link:label>
    <link:label id="lab_ecd_AllIndividualsMember_label_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Individuals [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllIndividualsMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AllIndividualsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllIndividualsMember" xlink:to="lab_ecd_AllIndividualsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_019bdc32-ac19-7f59-bb6b-09504ab011fb_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeDomain" xlink:to="lab_us-gaap_LongtermDebtTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresAbstract_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueDisclosuresAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresAbstract" xlink:to="lab_us-gaap_FairValueDisclosuresAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryIndName_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ForgoneRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryIndName" xlink:to="lab_ecd_ForgoneRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-over-Year Change in Fair Value of Equity Awards Granted in Prior Years That are Outstanding and Unvested</link:label>
    <link:label id="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember_label_en-US" xlink:label="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Year-over-Year Change in Fair Value of Equity Awards Granted in Prior Years That are Outstanding and Unvested [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:to="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_019bdc32-ab5f-7eec-abc5-44976f164ec1_terseLabel_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments, at fair value</link:label>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherShortTermInvestments" xlink:to="lab_us-gaap_OtherShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock_019bdc32-ac93-78e2-bd37-c203406ec5d6_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Derivative Instruments</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Derivative Instruments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfDerivativeInstrumentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:to="lab_us-gaap_ScheduleOfDerivativeInstrumentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis</link:label>
    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_label_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ErrCompAnalysisTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ErrCompAnalysisTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ErrCompAnalysisTextBlock" xlink:to="lab_ecd_ErrCompAnalysisTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_019bdc32-ac18-73fd-8266-e30a948b48b8_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:to="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_019bdc32-ac19-7def-9b84-4b2c794890b9_terseLabel_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_label_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IndefinitelivedIntangibleAssetsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:to="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss_019bdc32-ab5f-7364-a9ca-3b9647819f5f_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IntangibleAssetsAcquired_019bdc32-ac94-7521-a6bf-b9512ee62575_terseLabel_en-US" xlink:label="lab_skwd_IntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_skwd_IntangibleAssetsAcquired_label_en-US" xlink:label="lab_skwd_IntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets Acquired</link:label>
    <link:label id="lab_skwd_IntangibleAssetsAcquired_documentation_en-US" xlink:label="lab_skwd_IntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Intangible Assets Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IntangibleAssetsAcquired" xlink:href="skwd-20260331.xsd#skwd_IntangibleAssetsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IntangibleAssetsAcquired" xlink:to="lab_skwd_IntangibleAssetsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_019bdc32-ac19-7a56-b76d-e9c5682acc57_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net change in unrealized (losses) gains on investments, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Gain (Loss), before Adjustment, after Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialPortfolioSegmentMember_019bdc32-ab5f-7e12-9ece-68fecee13e7f_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commercial</link:label>
    <link:label id="lab_us-gaap_CommercialPortfolioSegmentMember_label_en-US" xlink:label="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commercial Portfolio Segment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialPortfolioSegmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommercialPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialPortfolioSegmentMember" xlink:to="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated</link:label>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_Rule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:to="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition_019e0402-fc31-7f27-b3eb-29a67f47604f_terseLabel_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, beginning of period</link:label>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition_label_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense, After Acquisition</link:label>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition_documentation_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense, After Acquisition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:href="skwd-20260331.xsd#skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:to="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionsProFormaRevenue_019d77bd-5cef-7e09-8ee7-fa974f370f8b_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Revenue</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionsProFormaRevenue_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Pro Forma Information, Pro Forma Revenue</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessAcquisitionsProFormaRevenue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:to="lab_us-gaap_BusinessAcquisitionsProFormaRevenue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward_019bdc32-ac19-71b2-bd43-abcd84e58826_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Indefinite-Lived</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IndefiniteLivedIntangibleAssetsRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ErrCompRecoveryTable_terseLabel_en-US" xlink:label="lab_ecd_ErrCompRecoveryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Erroneously Awarded Compensation Recovery</link:label>
    <link:label id="lab_ecd_ErrCompRecoveryTable_label_en-US" xlink:label="lab_ecd_ErrCompRecoveryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Erroneously Awarded Compensation Recovery [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ErrCompRecoveryTable" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_ErrCompRecoveryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ErrCompRecoveryTable" xlink:to="lab_ecd_ErrCompRecoveryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_Security12bTitle_019bdc32-ac94-7b76-82b3-2bb1c41d2eb6_terseLabel_en-US" xlink:label="lab_dei_Security12bTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title of 12(b) Security</link:label>
    <link:label id="lab_dei_Security12bTitle_label_en-US" xlink:label="lab_dei_Security12bTitle" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Title of 12(b) Security</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_Security12bTitle" xlink:href="https://xbrl.sec.gov/dei/2025/dei-2025.xsd#dei_Security12bTitle"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_Security12bTitle" xlink:to="lab_dei_Security12bTitle" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RestrictedAssetsLloydsFundsHeld_019e16f3-4635-770c-baac-270e56801355_terseLabel_en-US" xlink:label="lab_skwd_RestrictedAssetsLloydsFundsHeld" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Funds at Lloyd's</link:label>
    <link:label id="lab_skwd_RestrictedAssetsLloydsFundsHeld_label_en-US" xlink:label="lab_skwd_RestrictedAssetsLloydsFundsHeld" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Assets, Lloyd's Funds Held</link:label>
    <link:label id="lab_skwd_RestrictedAssetsLloydsFundsHeld_documentation_en-US" xlink:label="lab_skwd_RestrictedAssetsLloydsFundsHeld" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Restricted Assets, Lloyd's Funds Held</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RestrictedAssetsLloydsFundsHeld" xlink:href="skwd-20260331.xsd#skwd_RestrictedAssetsLloydsFundsHeld"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RestrictedAssetsLloydsFundsHeld" xlink:to="lab_skwd_RestrictedAssetsLloydsFundsHeld" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_019bdc32-ab5f-736f-a791-ed086ed6a282_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Per share data:</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EarningsPerShareAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareAbstract" xlink:to="lab_us-gaap_EarningsPerShareAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_019bdc32-ac94-746a-8a09-acbae8f69f10_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Paid, net of reinsurance, related to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NonCompetesMember_019bdc32-ac94-7925-9d0e-b27e76506a69_terseLabel_en-US" xlink:label="lab_skwd_NonCompetesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-competes</link:label>
    <link:label id="lab_skwd_NonCompetesMember_label_en-US" xlink:label="lab_skwd_NonCompetesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Competes [Member]</link:label>
    <link:label id="lab_skwd_NonCompetesMember_documentation_en-US" xlink:label="lab_skwd_NonCompetesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Non-Competes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NonCompetesMember" xlink:href="skwd-20260331.xsd#skwd_NonCompetesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NonCompetesMember" xlink:to="lab_skwd_NonCompetesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProfessionalFeesAndReimbursementsMember_019bdc32-ab5f-740c-ba22-4a9f56dba9f5_terseLabel_en-US" xlink:label="lab_skwd_ProfessionalFeesAndReimbursementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Professional fees and reimbursements</link:label>
    <link:label id="lab_skwd_ProfessionalFeesAndReimbursementsMember_label_en-US" xlink:label="lab_skwd_ProfessionalFeesAndReimbursementsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Professional Fees And Reimbursements [Member]</link:label>
    <link:label id="lab_skwd_ProfessionalFeesAndReimbursementsMember_documentation_en-US" xlink:label="lab_skwd_ProfessionalFeesAndReimbursementsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Professional Fees And Reimbursements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProfessionalFeesAndReimbursementsMember" xlink:href="skwd-20260331.xsd#skwd_ProfessionalFeesAndReimbursementsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProfessionalFeesAndReimbursementsMember" xlink:to="lab_skwd_ProfessionalFeesAndReimbursementsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_019bdc32-ac94-7f6d-a406-f7a297b20c23_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:to="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings_019bdc32-ac19-7363-a9ff-58d1e9c62666_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pre-tax gain (loss) adjustment expenses</link:label>
    <link:label id="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings_label_en-US" xlink:label="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Fair Value Hedges Recognized in Earnings</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:to="lab_us-gaap_GainLossOnFairValueHedgesRecognizedInEarnings" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TrancheBDDTLMember_019bdc32-ab5f-7a66-b2dd-4f8aa26d3bcd_terseLabel_en-US" xlink:label="lab_skwd_TrancheBDDTLMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tranche B DDTL</link:label>
    <link:label id="lab_skwd_TrancheBDDTLMember_label_en-US" xlink:label="lab_skwd_TrancheBDDTLMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tranche B DDTL [Member]</link:label>
    <link:label id="lab_skwd_TrancheBDDTLMember_documentation_en-US" xlink:label="lab_skwd_TrancheBDDTLMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Tranche B DDTL</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TrancheBDDTLMember" xlink:href="skwd-20260331.xsd#skwd_TrancheBDDTLMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TrancheBDDTLMember" xlink:to="lab_skwd_TrancheBDDTLMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NumberOfUnderwritingDivisions_019bdc32-ac19-7770-9c4a-6d8068a6941b_terseLabel_en-US" xlink:label="lab_skwd_NumberOfUnderwritingDivisions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of underwriting divisions</link:label>
    <link:label id="lab_skwd_NumberOfUnderwritingDivisions_label_en-US" xlink:label="lab_skwd_NumberOfUnderwritingDivisions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Underwriting Divisions</link:label>
    <link:label id="lab_skwd_NumberOfUnderwritingDivisions_documentation_en-US" xlink:label="lab_skwd_NumberOfUnderwritingDivisions" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number of Underwriting Divisions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NumberOfUnderwritingDivisions" xlink:href="skwd-20260331.xsd#skwd_NumberOfUnderwritingDivisions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NumberOfUnderwritingDivisions" xlink:to="lab_skwd_NumberOfUnderwritingDivisions" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_019bdc32-ac18-70c4-9eec-cd9a0dec6102_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Held-to-maturity, gross unrealized losses</link:label>
    <link:label id="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Accumulated Loss [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="skwd-20260331.xsd#skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:to="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract_019bdc32-ac94-7d92-bd1b-f30ff0188418_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Denominator</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted, Adjustment [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:to="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_019bdc32-ac94-7456-92cb-e98152bc8ec8_verboseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amortization expense</link:label>
    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_019bdc32-ac94-7aae-95fc-4e46d247a85d_terseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization expense</link:label>
    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_label_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amortization of Deferred Charges</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfDeferredCharges" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AmortizationOfDeferredCharges"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AmortizationOfDeferredCharges" xlink:to="lab_us-gaap_AmortizationOfDeferredCharges" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationLineItems_019bdc32-ac93-709c-b4b5-77131efff1a7_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationLineItems" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockSharesAcquired_019dcf5c-3aac-715d-b136-6faed9828510_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockSharesAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Shares acquired (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockSharesAcquired_label_en-US" xlink:label="lab_us-gaap_TreasuryStockSharesAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Shares, Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockSharesAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_TreasuryStockSharesAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockSharesAcquired" xlink:to="lab_us-gaap_TreasuryStockSharesAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgDiscLineItems_label_en-US" xlink:label="lab_ecd_AwardTmgDiscLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Disclosures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgDiscLineItems" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_AwardTmgDiscLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgDiscLineItems" xlink:to="lab_ecd_AwardTmgDiscLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_019bdc32-ac18-7fb7-8309-96eb763547fd_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rage Range [Domain]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Domain]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:href="skwd-20260331.xsd#skwd_DebtInstrumentFixedRatePeriodDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:to="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_019bdc32-ac19-7659-89df-187d5be5aade_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Gain (Loss) on Securities</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain (Loss) on Securities [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GainLossOnInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:to="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FederalHomeLoanBankAdvancesMember_019bdc32-ac19-712e-8212-b3e7cab95826_terseLabel_en-US" xlink:label="lab_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Federal Home Loan Bank Advances</link:label>
    <link:label id="lab_us-gaap_FederalHomeLoanBankAdvancesMember_label_en-US" xlink:label="lab_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Federal Home Loan Bank Advances [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FederalHomeLoanBankAdvancesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:to="lab_us-gaap_FederalHomeLoanBankAdvancesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019d47db-86e5-7fa6-af9d-6ceb93115119_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, beginning of period, net of reinsurance</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019bdc32-ac94-703e-b9b8-c9a77ee0c90a_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Net reserves for losses and LAE, end of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_StrategicPartnerSyndicatesMember_019d77ac-4c4a-7e82-92cb-226e891aac17_terseLabel_en-US" xlink:label="lab_skwd_StrategicPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Strategic partner syndicates</link:label>
    <link:label id="lab_skwd_StrategicPartnerSyndicatesMember_label_en-US" xlink:label="lab_skwd_StrategicPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Strategic Partner Syndicates [Member]</link:label>
    <link:label id="lab_skwd_StrategicPartnerSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_StrategicPartnerSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Strategic Partner Syndicates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_StrategicPartnerSyndicatesMember" xlink:href="skwd-20260331.xsd#skwd_StrategicPartnerSyndicatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_StrategicPartnerSyndicatesMember" xlink:to="lab_skwd_StrategicPartnerSyndicatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability_019e08ba-52c6-73ea-9a7c-0d08efe57b7f_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Funds held for others</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Funds Held Under Reinsurance Agreements, Liability</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Funds Held Under Reinsurance Agreements, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:href="skwd-20260331.xsd#skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:to="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedFundsHeldUnderReinsuranceAgreementsLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AlignedSyndicatesMember_019de301-9211-7588-b9ea-c30e00918063_terseLabel_en-US" xlink:label="lab_skwd_AlignedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aligned Syndicates</link:label>
    <link:label id="lab_skwd_AlignedSyndicatesMember_label_en-US" xlink:label="lab_skwd_AlignedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aligned Syndicates [Member]</link:label>
    <link:label id="lab_skwd_AlignedSyndicatesMember_documentation_en-US" xlink:label="lab_skwd_AlignedSyndicatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Aligned Syndicates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AlignedSyndicatesMember" xlink:href="skwd-20260331.xsd#skwd_AlignedSyndicatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AlignedSyndicatesMember" xlink:to="lab_skwd_AlignedSyndicatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_019bdc32-ac94-7055-a30e-538f7ebc65c7_terseLabel_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_label_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule Of Underwriting, Acquisition and Insurance Expenses [Table Text Block]</link:label>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_documentation_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Schedule Of Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:href="skwd-20260331.xsd#skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:to="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_019bdc32-ab5f-76de-a586-4f45f5715019_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReinsuranceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceTextBlock" xlink:to="lab_us-gaap_ReinsuranceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLoss_019bdc32-ac19-7ecc-9042-638c11e82eb9_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_019bdc32-ac19-7a44-b1ea-cdfa95cf67a0_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_019bdc32-ac19-7cfd-abe0-eb6ccca71e99_verboseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_label_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLoss" xlink:to="lab_us-gaap_NetIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_019bdc32-ab5f-7fd3-9088-107068c73da3_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_019bdc32-ac19-7751-a81d-2b82a762bbf5_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available-for-sale and held-to-maturity, gross unrealized losses</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="skwd-20260331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AccidentHealthMember_019bdc32-ac93-7e73-927a-9cf6d63d091c_terseLabel_en-US" xlink:label="lab_skwd_AccidentHealthMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident &amp; Health</link:label>
    <link:label id="lab_skwd_AccidentHealthMember_label_en-US" xlink:label="lab_skwd_AccidentHealthMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accident &amp; Health [Member]</link:label>
    <link:label id="lab_skwd_AccidentHealthMember_documentation_en-US" xlink:label="lab_skwd_AccidentHealthMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Accident &amp; Health</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AccidentHealthMember" xlink:href="skwd-20260331.xsd#skwd_AccidentHealthMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AccidentHealthMember" xlink:to="lab_skwd_AccidentHealthMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SPA1925Member_019d77ce-4ba2-7e7f-b184-cc0b1a8dbb48_terseLabel_en-US" xlink:label="lab_skwd_SPA1925Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SPA1925</link:label>
    <link:label id="lab_skwd_SPA1925Member_label_en-US" xlink:label="lab_skwd_SPA1925Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SPA1925 [Member]</link:label>
    <link:label id="lab_skwd_SPA1925Member_documentation_en-US" xlink:label="lab_skwd_SPA1925Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">SPA1925</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SPA1925Member" xlink:href="skwd-20260331.xsd#skwd_SPA1925Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SPA1925Member" xlink:to="lab_skwd_SPA1925Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TrancheADDTLMember_019bdc32-ab5f-7a54-b4f2-98cb1298fa9f_terseLabel_en-US" xlink:label="lab_skwd_TrancheADDTLMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tranche A DDTL</link:label>
    <link:label id="lab_skwd_TrancheADDTLMember_label_en-US" xlink:label="lab_skwd_TrancheADDTLMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tranche A DDTL [Member]</link:label>
    <link:label id="lab_skwd_TrancheADDTLMember_documentation_en-US" xlink:label="lab_skwd_TrancheADDTLMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Tranche A DDTL</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TrancheADDTLMember" xlink:href="skwd-20260331.xsd#skwd_TrancheADDTLMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TrancheADDTLMember" xlink:to="lab_skwd_TrancheADDTLMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_019bdc32-ac94-767a-a0c6-004422333dc1_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting Information [Line Items]</link:label>
    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_label_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting Information [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingInformationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SegmentReportingInformationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingInformationLineItems" xlink:to="lab_us-gaap_SegmentReportingInformationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_019bdc32-ab60-77f7-b7c4-0e74237fd839_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments, unfunded commitment</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_label_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments, Unfunded Commitment</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_documentation_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investments, Unfunded Commitment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:href="skwd-20260331.xsd#skwd_EquityMethodInvestmentsUnfundedCommitment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:to="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_019df2c6-291d-7e85-9c9f-eec92d31275e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock acquired</link:label>
    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_label_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for Repurchase of Common Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsForRepurchaseOfCommonStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:to="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrAdoptionDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adoption Date</link:label>
    <link:label id="lab_ecd_TrdArrAdoptionDate_label_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Adoption Date</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrAdoptionDate" xlink:to="lab_ecd_TrdArrAdoptionDate" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract_019bdc32-ab5f-75f6-b6c8-dd99247095d2_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract"/>
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    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019bdc32-ab60-7956-894b-12cc4a3c9ba5_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019bdc32-ab60-7130-a540-46dda713d224_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, beginning of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_019bdc32-ab60-7756-a75c-704e514f4658_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, end of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrTerminationDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrTerminationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Termination Date</link:label>
    <link:label id="lab_ecd_TrdArrTerminationDate_label_en-US" xlink:label="lab_ecd_TrdArrTerminationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Termination Date</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrTerminationDate" xlink:to="lab_ecd_TrdArrTerminationDate" xlink:type="arc" order="1"/>
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    <link:label id="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_InsiderTrdPoliciesProcAdoptedFlag"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Identifiable Intangible Asset, Indefinite-Lived</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets"/>
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    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_019bdc32-ac94-7136-9d94-999aa1e20881_verboseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Basic (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_019bdc32-ac94-7099-a865-90e6b00c4a0f_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic weighted-average common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
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    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_019bdc32-ac18-7c2d-8b0d-28b4a630b196_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted [Table Text Block]</link:label>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionDomain_019bdc32-ac19-7ba1-bce5-49a93152efdc_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Domain]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionDomain_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transaction [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RelatedPartyTransactionDomain"/>
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    <link:label id="lab_us-gaap_SegmentReportingAbstract_label_en-US" xlink:label="lab_us-gaap_SegmentReportingAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_SegmentReportingAbstract"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Net, Amortization Expense, Fiscal Year Maturity [Abstract]</link:label>
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    <link:label id="lab_us-gaap_DebtDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtDisclosureAbstract"/>
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    <link:label id="lab_us-gaap_CostsAndExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_CostsAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Costs and Expenses [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostsAndExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CostsAndExpensesAbstract"/>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions_019bdc32-ab5f-718d-818f-cd6d4bfe0d6e_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of securities, allowance for credit loss</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Allowance for Credit Loss, Number of Positions</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Allowance for Credit Loss, Number of Positions</link:label>
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    <link:label id="lab_srt_ConsolidatedEntitiesAxis_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
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    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_019bdc32-ab5f-709f-9986-6d2fc7a1ee1b_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, par value (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_label_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Par or Stated Value Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommonStockParOrStatedValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:to="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery_019bdc32-ab5f-7eb3-b974-001a1955d553_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Recoveries of amounts previously written off</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest, Allowance for Credit Loss, Recovery</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UseOfEstimates_019bdc32-ac94-7631-bdcf-59a200bcf812_terseLabel_en-US" xlink:label="lab_us-gaap_UseOfEstimates" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Use of Estimates</link:label>
    <link:label id="lab_us-gaap_UseOfEstimates_label_en-US" xlink:label="lab_us-gaap_UseOfEstimates" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Use of Estimates, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UseOfEstimates" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_UseOfEstimates"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UseOfEstimates" xlink:to="lab_us-gaap_UseOfEstimates" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet_019d7783-eaa8-7706-b900-cc0dfcda29f0_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables, net</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Reinsurance Recoverable, Net</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Reinsurance Recoverable, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:href="skwd-20260331.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:to="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements_019bdc32-ac19-78b3-b026-491394abdafa_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Settlements</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Settlements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSettlements" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_InsiderTradingArrLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingArrLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Arrangements [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingArrLineItems" xlink:href="https://xbrl.sec.gov/ecd/2025/ecd-2025.xsd#ecd_InsiderTradingArrLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingArrLineItems" xlink:to="lab_ecd_InsiderTradingArrLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesMember_019bdc32-ac18-7528-a0b9-1be32ad5824e_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesMember_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_EquitySecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesMember" xlink:to="lab_us-gaap_EquitySecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019bdc32-ab60-7626-9a7d-e3aa165d9da1_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Available-for-sale allowance for credit losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019bdc32-ab60-7a61-ad81-9e5a9d74e83a_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Allowance for Credit Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019bdc32-ab60-7ee2-a905-4f983c50e2ea_periodStartLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019bdc32-ab60-7d5a-89b4-253e39680d4a_periodEndLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Allowance for Credit Loss, Excluding Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Liabilities_019bdc32-ab5f-7789-89f3-9c5068136027_totalLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities</link:label>
    <link:label id="lab_us-gaap_Liabilities_label_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Liabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Liabilities" xlink:to="lab_us-gaap_Liabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_019bdc32-ac18-7335-951f-2ae37702c9e0_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Antidilutive Securities, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Antidilutive Securities, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AntidilutiveSecuritiesNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:to="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage_019d47c0-64b3-7829-affd-921284500b0b_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of credit facility, commitment fee percentage</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit Facility, Commitment Fee Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LineOfCreditFacilityCommitmentFeePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:to="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA_019d7785-8f08-70e1-b820-e68eea40399b_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred policy acquisition costs and VOBA</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Deferred Policy Acquisition Costs and VOBA</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Deferred Policy Acquisition Costs and VOBA</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:href="skwd-20260331.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:to="lab_skwd_BusinessCombinationRecognizedAssetAcquiredDeferredPolicyAcquisitionCostsAndVOBA" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost</link:label>
    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_label_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost [Member]</link:label>
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    <link:label id="lab_ecd_MtrlTermsOfTrdArrTextBlock_label_en-US" xlink:label="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Material Terms of Trading Arrangement [Text Block]</link:label>
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    <link:label id="lab_skwd_FeebasedServiceExpenses_019de2eb-8aa0-71e8-907d-78c82ada31b9_terseLabel_en-US" xlink:label="lab_skwd_FeebasedServiceExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fee&#8209;based service expenses</link:label>
    <link:label id="lab_skwd_FeebasedServiceExpenses_label_en-US" xlink:label="lab_skwd_FeebasedServiceExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fee&#8209;based Service Expenses</link:label>
    <link:label id="lab_skwd_FeebasedServiceExpenses_documentation_en-US" xlink:label="lab_skwd_FeebasedServiceExpenses" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fee&#8209;based Service Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FeebasedServiceExpenses" xlink:href="skwd-20260331.xsd#skwd_FeebasedServiceExpenses"/>
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    <link:label id="lab_skwd_Syndicate1969Member_019d77d1-86af-7f83-8aba-bb5f76d11127_terseLabel_en-US" xlink:label="lab_skwd_Syndicate1969Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate 1969</link:label>
    <link:label id="lab_skwd_Syndicate1969Member_label_en-US" xlink:label="lab_skwd_Syndicate1969Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate 1969 [Member]</link:label>
    <link:label id="lab_skwd_Syndicate1969Member_documentation_en-US" xlink:label="lab_skwd_Syndicate1969Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate 1969</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_Syndicate1969Member" xlink:href="skwd-20260331.xsd#skwd_Syndicate1969Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_Syndicate1969Member" xlink:to="lab_skwd_Syndicate1969Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_Syndicate1969CapacityMember_019d77a8-2f75-7107-a192-9624fa732633_terseLabel_en-US" xlink:label="lab_skwd_Syndicate1969CapacityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Syndicate 1969 capacity - with fees</link:label>
    <link:label id="lab_skwd_Syndicate1969CapacityMember_label_en-US" xlink:label="lab_skwd_Syndicate1969CapacityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Syndicate 1969 Capacity [Member]</link:label>
    <link:label id="lab_skwd_Syndicate1969CapacityMember_documentation_en-US" xlink:label="lab_skwd_Syndicate1969CapacityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Syndicate 1969 Capacity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_Syndicate1969CapacityMember" xlink:href="skwd-20260331.xsd#skwd_Syndicate1969CapacityMember"/>
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