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    <link:label id="lab_ecd_TradingArrByIndTable_label_en-US" xlink:label="lab_ecd_TradingArrByIndTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangements, by Individual [Table]</link:label>
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    <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>
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    <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/2026/elts/us-gaap-2026.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"/>
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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:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GlobalAgricultureMember" xlink:to="lab_skwd_GlobalAgricultureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_Security12bTitle_019e3bd8-6167-78b5-8ba6-dc86960ea509_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>
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    <link:label id="lab_us-gaap_SubsequentEventMember_019fcb32-4cd0-7d6a-91cc-9b0c05832178_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event</link:label>
    <link:label id="lab_us-gaap_SubsequentEventMember_label_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsequentEventMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventMember" xlink:to="lab_us-gaap_SubsequentEventMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SMA1Member_019e3bd8-61f1-7b0d-887a-cdc6dd624c6c_terseLabel_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SMA1</link:label>
    <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-20260630.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"/>
    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_019e3bd8-6168-7b3c-939a-46289848690d_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/2026/elts/us-gaap-2026.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_EquityMethodInvestmentsMember_019e3bd8-6167-7ffc-b676-dc26d6fc9d02_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/2026/elts/us-gaap-2026.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_DebtSecuritiesAvailableForSaleTable_019e3bd8-6167-72dd-9551-b21d3a1810b8_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/2026/elts/us-gaap-2026.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_DerivativeInstrumentsGainLossByHedgingRelationshipByIncomeStatementLocationByDerivativeInstrumentRiskTable_019e3bd8-6167-7d89-b439-20b97a19d3ad_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipByIncomeStatementLocationByDerivativeInstrumentRiskTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative Instruments, Gain (Loss) [Table]</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipByIncomeStatementLocationByDerivativeInstrumentRiskTable_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipByIncomeStatementLocationByDerivativeInstrumentRiskTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instruments, Gain (Loss) [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipByIncomeStatementLocationByDerivativeInstrumentRiskTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsGainLossByHedgingRelationshipByIncomeStatementLocationByDerivativeInstrumentRiskTable"/>
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    <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/2026/ecd-2026.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_FinancialInstrumentAxis_019e3bd8-60c7-7082-991d-bdb48e95f6af_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/2026/elts/us-gaap-2026.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_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/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingAbstract" xlink:to="lab_us-gaap_SegmentReportingAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock_019e3bd8-6168-7b1c-8e24-fa5c33b33844_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">Intangible Asset, Finite-Lived, and Capitalized Cost, Software to be Sold, Leased, or Marketed, Estimated 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">Intangible Asset, Finite-Lived, and Capitalized Cost, Software to be Sold, Leased, or Marketed, Estimated 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/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock"/>
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    <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>
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    <link:label id="lab_us-gaap_TrademarksMember_019e3bd8-60c7-7128-a4d5-c9b2cf7858ba_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>
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    <link:label id="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract_019e3bd8-60c7-77d9-80a0-06f054c80b89_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesUnrealizedGainLossAbstract"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_019e3bd8-60c7-7805-8293-b5a7c5622614_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/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract"/>
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    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_019e3bd8-60c7-72de-a466-593ca3ffcf28_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contract asset after allowance for credit loss</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contract with Customer, Asset, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerAssetNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ContractWithCustomerAssetNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ContractWithCustomerAssetNet" xlink:to="lab_us-gaap_ContractWithCustomerAssetNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePayable_019e3bd8-60c7-75cb-9395-26f2e4c8c30c_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/2026/elts/us-gaap-2026.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"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Investment in Debt and Equity Securities, Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsMarketableSecurities"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease_019e3bd8-5ff8-7557-8b3f-ad0d06d2c248_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease" 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_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease" 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, Period Increase (Decrease)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossPeriodIncreaseDecrease"/>
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    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefit_019e3bd8-61f1-7b94-8c7a-f6873044e471_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/2026/elts/us-gaap-2026.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_srt_ConsolidatedEntitiesAxis_019e3bd8-6167-7e31-bb8b-5c034c6e7084_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <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>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidatedEntitiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesAxis" xlink:to="lab_srt_ConsolidatedEntitiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_019e3bd8-6167-77d2-92c7-67bcda540a7f_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>
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    <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_skwd_SyndicateMember_019e3bd8-6167-7c86-a630-a15407c2a977_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-20260630.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_AssetBackedSecuritiesMember_019e3bd8-6168-7152-8bbd-0fc0fea3e781_terseLabel_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other asset-backed securities</link:label>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetBackedSecuritiesMember" xlink:to="lab_us-gaap_AssetBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_019e3bd8-60c7-7c8e-920e-501ce139ca7c_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-20260630.xsd#skwd_UnsecuredSubordinatedNotesMember"/>
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    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward_019e3bd8-60c7-7159-9d4f-f5fcc845893e_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">Intangible Asset, Indefinite-Lived [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IndefiniteLivedIntangibleAssetsRollForward"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract"/>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_FeeIncome"/>
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    <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>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_019e3bd8-60c8-7ee1-a5a6-9bd955024738_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/2026/elts/us-gaap-2026.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_IntangibleAssetsNetExcludingGoodwill_019f5fe6-f925-7116-958c-95ddfb541a00_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross intangible assets, ending balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Excluding Goodwill, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagedPremium_019e3bd8-61f1-7d46-9e22-a3b1c76168b9_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-20260630.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_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/2026/ecd-2026.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_NumberOfReportableSegments_019e3bd8-6168-731a-9e9a-1e88dd18b8ef_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/2026/elts/us-gaap-2026.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_ScheduleOfDerivativeInstrumentsTextBlock_019e3bd8-6168-7aa6-8194-48f0a17ab9d7_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/2026/elts/us-gaap-2026.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_skwd_MeasurementInputIncrementalCostOfCapitalMember_019e3bd8-60c7-7cd2-8085-a6e718551bc2_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-20260630.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_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_019e3bd8-60c7-7ed2-8457-f89da57d8adc_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_019e3bd8-60c7-7c5f-bfca-89d83cab3d4f_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>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Excluding Accrued Interest, before Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressCityOrTown_019e3bd8-60c7-74b2-9cd4-783903d450f1_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/2026/dei-2026.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_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_019e3bd8-6167-75da-9de8-94b6766b26cd_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-20260630.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_us-gaap_DerivativeFairValueOfDerivativeNet_019e3bd8-60c7-71ec-b41e-d3dcf6619c73_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/2026/elts/us-gaap-2026.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_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/2026/elts/us-gaap-2026.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_skwd_BusinessCombinationRecognizedLiabilityAssumedUnearnedPremiums_019e3bd8-60c7-707f-9961-7f45890eaa37_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-20260630.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_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/2026/elts/us-gaap-2026.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_us-gaap_FiniteLivedIntangibleAssetsNet_019e3bd8-6168-7d96-9205-12f9b50e384c_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">Intangible Asset, Finite-Lived, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_ecd_PeerGroupTotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeerGroupTotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:to="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_019e3bd8-6167-7469-9e15-6e6f4843a237_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/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredLloydsFunds_019e3bd8-6167-74b7-bc83-795bf4da4b4d_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-20260630.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_ProceedsFromStockPlans_019e3bd8-60c7-7a8c-b5d7-c442218177da_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/2026/elts/us-gaap-2026.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_FairValueInputsLevel2Member_019e3bd8-60c7-7626-815c-fb67221e134a_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_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/2026/ecd-2026.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_LicenseMember_019e3bd8-60c8-7897-9c7e-9b882c1e7bb1_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/2026/elts/us-gaap-2026.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"/>
    <link:label id="lab_us-gaap_OtherExpenses_019e3bd8-61f1-7d4a-bff9-29db48c2bae3_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/2026/elts/us-gaap-2026.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_us-gaap_SubsequentEventTypeAxis_019fcb32-4cd0-7d6e-861d-beaba6e1a9d3_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeAxis_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsequentEventTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeAxis" xlink:to="lab_us-gaap_SubsequentEventTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTable_019e3bd8-6168-7090-99d7-5be994ee09a8_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/2026/elts/us-gaap-2026.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_SecuritiesHeldAsCollateralAtFairValue_019e3bd8-5ff8-711f-9b09-f68985eb7458_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/2026/elts/us-gaap-2026.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_InsuranceCommissionsAndFees_019e3bd8-6168-7a97-b264-d684f684ca83_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and fee income</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Commissions and Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissionsAndFees" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceCommissionsAndFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceCommissionsAndFees" xlink:to="lab_us-gaap_InsuranceCommissionsAndFees" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_019e3bd8-60c7-7d7d-af84-39cf9dc38ca1_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-20260630.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_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_019e3bd8-61f1-71fd-b71f-7c1e39ebab8b_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/2026/elts/us-gaap-2026.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_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock_019e3bd8-6167-7fe8-9264-8b42060a3b7c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting</link:label>
    <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">Segment Reporting [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:to="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MunicipalBondsMember_019e3bd8-6168-7f25-b323-6755ca327548_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/2026/elts/us-gaap-2026.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_us-gaap_UseOfEstimates_019e3bd8-5ff8-7589-a258-074b3d671e59_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/2026/elts/us-gaap-2026.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_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_019e3bd8-6168-7e15-a971-f52d5a1684ca_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/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyTransactionsByRelatedPartyAxis"/>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019e3bd8-6168-773b-92d3-ae288b6d1471_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>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_019e3bd8-60c7-7699-8a61-d95754f5601d_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentPeriodEndDate_019e3bd8-6168-7871-8c79-426c71600058_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/2026/dei-2026.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_skwd_EnergyMember_019e3bd8-60c7-7468-af46-44b35f2c59b7_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-20260630.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_us-gaap_DebtInstrumentFaceAmount_019e3bd8-60c7-7f8d-a428-30d65e5c71c9_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/2026/elts/us-gaap-2026.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_us-gaap_DebtInstrumentTerm_019e3bd8-60c7-701b-a9f6-b4fd0b44e881_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/2026/elts/us-gaap-2026.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_DebtSecuritiesAvailableForSaleRealizedLoss_019e3bd8-60c8-7b5c-bad9-8ecdcb3af250_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/2026/elts/us-gaap-2026.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_skwd_HospitalityPortfolioSegmentMember_019e3bd8-6167-715d-9a88-5662d314fc01_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-20260630.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_019e3bd8-60c7-79fa-b057-b69adb2a0df1_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-20260630.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_skwd_StockUnitsMember_019e3bd8-60c7-7fc1-811b-48cbe0482291_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-20260630.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_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_019e3bd8-5ff8-7076-91e7-26f73c3483c4_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/2026/elts/us-gaap-2026.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"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_019e3bd8-6167-7058-979f-57b4a4e7d7e2_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-20260630.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_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_019e3bd8-60c7-78c9-807e-1d3391a6b454_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/2026/elts/us-gaap-2026.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_ShortTermInvestmentFairValueDisclosure_019e3bd8-6167-7ac1-8b97-ff956f6046a3_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-20260630.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_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019e3bd8-60c8-7f71-96f3-7eafa2491bef_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/2026/elts/us-gaap-2026.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_dei_EntityShellCompany_019e3bd8-6168-704c-bc3c-12fdd17eb9e0_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/2026/dei-2026.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_srt_ConsolidationItemsDomain_019e3bd8-6167-7941-b246-ebfa9cfe1fdd_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/2026/elts/srt-2026.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_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_019e3bd8-6168-79b5-a1af-ceb447222263_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-20260630.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_019e3bd8-60c7-7710-ab49-2eefa107ba80_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-20260630.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_us-gaap_EarningsPerShareTextBlock_019e3bd8-61f1-7114-9bbf-4978e972dc60_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/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareTextBlock" xlink:to="lab_us-gaap_EarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_019e3bd8-6168-7e73-82e4-af70bfc64cc3_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/2026/elts/us-gaap-2026.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_dei_DocumentFiscalPeriodFocus_019e3bd8-6167-7fb5-9556-40e368d9ec40_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/2026/dei-2026.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_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/2026/ecd-2026.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_Liabilities_019e3bd8-6168-73e7-9001-c1c54b8a8a75_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/2026/elts/us-gaap-2026.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_dei_TradingSymbol_019e3bd8-6167-7501-b393-67a80d03ca32_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/2026/dei-2026.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_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019e3bd8-60c7-70cf-ac9d-13decb6b3d61_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 $6,228 and $7,000, respectively) (amortized cost of $2,206,626 and $1,848,755, respectively)</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_019e3bd8-60c7-723a-9910-32cf959599dc_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_019e3bd8-60c7-7ced-b18f-6adf893b1d4e_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_019e3bd8-60c7-770c-8ad0-14531c15b78e_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/2026/elts/us-gaap-2026.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_PaymentsToAcquirePropertyPlantAndEquipment_019e3bd8-61f2-79ae-a031-4066f069d0de_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of property and equipment</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Property, Plant, and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:to="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EnergySolutionsMember_019e3bd8-61f1-751d-a61d-a14e898a9b36_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-20260630.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_ScheduleOfRecognizedIdentifiedAssetsAcquiredAndLiabilitiesAssumedTableTextBlock_019e3bd8-60c7-70dd-95c0-c62b56e283d8_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/2026/elts/us-gaap-2026.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_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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_CoSelectedMeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureName" xlink:to="lab_ecd_CoSelectedMeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss_019e3bd8-6168-7ff4-b64d-d81a89d0179c_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total unrealized gains (loss) for the period recognized in accumulated comprehensive income (loss)</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" 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 Other Comprehensive Income (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInOtherComprehensiveIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax_019e3bd8-60c8-7064-9a57-45e155091d58_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/2026/elts/us-gaap-2026.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_PaymentsToAcquireAvailableForSaleSecuritiesDebt_019e3bd8-60c7-76e1-8f1a-893af7932228_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/2026/elts/us-gaap-2026.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_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/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:to="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedLiabilityForClaimsAndClaimsAdjustmentExpense_019e3bd8-6167-7a79-ad0b-7f275044125b_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-20260630.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_skwd_FHLBLoanMember_019e3bd8-60c7-784c-b01d-970cce9b57d5_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-20260630.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_019e3bd8-60c7-76ad-88bb-2125874dfc10_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-20260630.xsd#skwd_GainOnSaleOfOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GainOnSaleOfOtherInvestments" xlink:to="lab_skwd_GainOnSaleOfOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityCommitmentFeePercentage_019e3bd8-6167-78d6-9574-7c988ccd3579_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/2026/elts/us-gaap-2026.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_us-gaap_CreditFacilityDomain_019e3bd8-6167-722b-83a9-6cd79c494904_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/2026/elts/us-gaap-2026.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_LiabilityForClaimsAndClaimsAdjustmentExpense_019e3bd8-6167-7cff-818d-cc20f0d46562_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_019e3bd8-6167-733d-96a9-b6af52fc3b26_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_019e3bd8-6167-79a8-a0c4-8546bdb2e045_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <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_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_019e3bd8-6167-7ef1-8a2c-5fc9647c70de_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/2026/elts/us-gaap-2026.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_SalesCommissionsAndFees_019e3bd8-60c7-7e0b-94d9-46f4cbd3fdf2_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_019e3bd8-6168-74b9-a193-e2255aacbdd2_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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet"/>
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    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_019e3bd8-61f1-7ddd-ac25-eb48814ef7be_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/2026/elts/us-gaap-2026.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_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss_019e3bd8-6168-7234-9d46-f32b49b4546b_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/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss"/>
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    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_019e3bd8-6168-786c-ba7d-0a9766174a43_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" 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 Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_019e3bd8-6168-7e41-8397-1449ff76edbb_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/2026/elts/us-gaap-2026.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_AwardTmgPredtrmndFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgPredtrmndFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Predetermined</link:label>
    <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/2026/ecd-2026.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_UnderwritingIncomeLoss_019e3bd8-60c7-75fe-b552-472ef27b16ec_totalLabel_en-US" xlink:label="lab_us-gaap_UnderwritingIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total underwriting revenues</link:label>
    <link:label id="lab_us-gaap_UnderwritingIncomeLoss_label_en-US" xlink:label="lab_us-gaap_UnderwritingIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting Income (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnderwritingIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnderwritingIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnderwritingIncomeLoss" xlink:to="lab_us-gaap_UnderwritingIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote</link:label>
    <link:label id="lab_ecd_AdjToPeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToPeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AdjToPeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToPeoCompFnTextBlock" xlink:to="lab_ecd_AdjToPeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_019e3bd8-6167-7ee6-a15a-4b164a375f81_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/2026/elts/us-gaap-2026.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_skwd_ProceedsFromPaymentsForDepositAccounting_019e3bd8-60c8-73b0-8e43-54504b84fbb3_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 (used in) 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-20260630.xsd#skwd_ProceedsFromPaymentsForDepositAccounting"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_019e3bd8-6168-750c-829d-f457ceb69b8e_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_019e3bd8-6168-7f60-8104-c3e42e0c6868_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/2026/elts/us-gaap-2026.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_us-gaap_EffectiveIncomeTaxRateContinuingOperations_019e3bd8-6168-7afd-8284-353602ccc6e2_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/2026/elts/us-gaap-2026.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_skwd_LoansHeldForInvestmentTerm_019e3bd8-6167-731b-a7c4-a5132be4f4a2_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-20260630.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_skwd_UnsecuredSubordinatedNotesDue2039Member_019e3bd8-61f1-720d-afe5-a89f7b82b396_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-20260630.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_019e3bd8-60c7-7c2e-963b-4f398f92fd37_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-20260630.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_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_019e3bd8-6168-72b2-bd4c-3c3bd7218591_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>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_label_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Share-Based Payment Arrangements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:to="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_019e3bd8-60c7-76f1-9da7-ca18cf73317c_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-20260630.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_ResidentialMortgageBackedSecuritiesMember_019e3bd8-6167-7b1d-be27-d44d5e87de46_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/2026/elts/us-gaap-2026.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_LongTermDebtFairValue_019e3bd8-60c7-7f4e-b207-a5f9265cbd98_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/2026/elts/us-gaap-2026.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_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_019e3bd8-5ff8-774f-ae87-2a8aa14aa789_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/2026/elts/us-gaap-2026.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_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_019e3bd8-60c7-7c39-ad81-78d0e5b8e758_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/2026/elts/us-gaap-2026.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_CollateralizedSecuritiesMember_019e3bd8-61f1-7d64-ae44-c59bfc78ac23_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/2026/elts/us-gaap-2026.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_Syndicate1971CapacityMember_019e3bd8-60c8-7326-9083-67e50677cbbc_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-20260630.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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_019e3bd8-60c7-7ce4-9e54-c6b8a537b41d_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/2026/elts/us-gaap-2026.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_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_019e3bd8-60c7-7206-b230-48a87e7f4a4b_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>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" 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, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_skwd_ApolloMember_019e3bd8-6168-7248-8c73-c627357582de_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-20260630.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_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_019e3bd8-61f1-7df7-a804-f1e4c9fe71e0_totalLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" 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_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" 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), and Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet" 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/2026/elts/us-gaap-2026.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_skwd_AgencyAgreementMember_019e3bd8-61f1-7afa-9cac-9596ecd97d44_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-20260630.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_us-gaap_DebtInstrumentNameDomain_019e3bd8-6168-703f-a823-ac22be63422f_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_DerivativeInstrumentsGainLossByHedgingRelationshipAxis_019e3bd8-6167-78f6-ab4a-37ceeb15ee8e_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/2026/elts/us-gaap-2026.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_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain_019e3bd8-61f1-759d-9f76-890cc0e78218_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" 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_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Accumulated Unrecognized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract_019e3bd8-6168-78ad-a2d8-7dd09b43f4e6_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:to="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_019e3bd8-6168-7833-89e6-94cd46b28a65_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/2026/elts/us-gaap-2026.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_ArenaSOPLPMember_019e3bd8-6168-7f00-a740-42f5cbdc1fa1_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-20260630.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_us-gaap_SubordinatedDebtMember_019e3bd8-60c7-75f2-a75e-bb055874aa59_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/2026/elts/us-gaap-2026.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_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues_019e3bd8-60c7-71ba-b985-f080a90fdcc2_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/2026/elts/us-gaap-2026.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_srt_AffiliatedEntityMember_019e3bd8-61f1-7a02-bf88-082c876ccf8f_terseLabel_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Affiliated entity</link:label>
    <link:label id="lab_srt_AffiliatedEntityMember_label_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Affiliated Entity [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_AffiliatedEntityMember" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_AffiliatedEntityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_AffiliatedEntityMember" xlink:to="lab_srt_AffiliatedEntityMember" 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/2026/ecd-2026.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_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/2026/elts/us-gaap-2026.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_us-gaap_EarningsPerShareReconciliationAbstract_019e3bd8-6167-71aa-bdb7-e088bc82f321_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/2026/elts/us-gaap-2026.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_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables_019e3bd8-60c7-7b56-8ae6-075148985aad_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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables"/>
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    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_019e3bd8-60c7-7e59-b3f3-45a2e94d9e3d_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/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable"/>
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    <link:label id="lab_skwd_NumberOfSubsidiaries_019e3bd8-61f1-7d8a-9aa0-99a33e116b9d_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-20260630.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_skwd_SubordinatedDebtNetMember_019e3bd8-6168-74db-bce9-5275ca62a25e_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-20260630.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_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_019e3bd8-5ff8-723a-9b87-e974ca03078a_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/2026/elts/us-gaap-2026.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_us-gaap_RelatedPartyTransactionAxis_019e3bd8-6167-72ed-b4b1-a176f3987b48_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/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyTransactionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionAxis" xlink:to="lab_us-gaap_RelatedPartyTransactionAxis" xlink:type="arc" order="1"/>
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    <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-20260630.xsd#skwd_ProfitCommissionAndConsortiumOverriderChargedToManagedSyndicatesMember"/>
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    <link:label id="lab_us-gaap_SegmentDomain_019e3bd8-60c7-7a78-9a8b-a7ea2da4cdea_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/2026/elts/us-gaap-2026.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_us-gaap_DebtDisclosureTextBlock_019e3bd8-60c8-7606-9c42-53365b2f4da4_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/2026/elts/us-gaap-2026.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_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensationForfeited_019fd7f9-5164-7e6a-808b-18ee401b57aa_negatedLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensationForfeited" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">(Acquisition) issuance of common stock (in shares)</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensationForfeited_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensationForfeited" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shares Issued, Shares, Share-Based Payment Arrangement, Forfeited</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensationForfeited" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensationForfeited"/>
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    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_019e3bd8-60c7-733c-ac3e-6e393e45c590_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/2026/elts/us-gaap-2026.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_ScheduleOfBusinessAcquisitionsByAcquisitionTable_019e3bd8-60c8-776a-815e-57558d1e0ac3_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_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/2026/elts/us-gaap-2026.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_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract_019e3bd8-6168-7786-9db1-8e9136cdccb7_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/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract"/>
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    <link:label id="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments_019e3bd8-6167-70f7-b8d0-0a69a3ee424f_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of equity method investments and other long-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:to="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_019e3bd8-61f2-7dc9-a507-41f01583631c_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stated interest rate</link:label>
    <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/2026/elts/us-gaap-2026.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_us-gaap_StockholdersEquity_019e3bd8-60c7-787e-ba1e-5ead7f5d069d_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_019e3bd8-60c7-733d-9d42-cc6b001b4855_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_019e3bd8-60c7-71cd-a27f-38b7ced5fa22_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/2026/elts/us-gaap-2026.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_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets_019e3bd8-61f1-771d-9ed8-d34a8221d382_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>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Asset Acquired, Other Asset, Noncurrent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets"/>
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    <link:label id="lab_us-gaap_AssetsAbstract_019e3bd8-60c7-7bd7-86c7-dc81823252ae_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/2026/elts/us-gaap-2026.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_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued_019e3bd8-5ff8-7308-b721-503cf4e12cbf_netLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Issuance of shares (in shares)</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued_019e3bd8-5ff8-77cb-8988-5120d5e1a32a_verboseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Skyward Specialty Insurance Group, Inc. common stock issued to existing Apollo common stockholders (in shares)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionEquityInterestsIssuedOrIssuableNumberOfSharesIssued"/>
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    <link:label id="lab_skwd_MiscellaneousFeeIncomeMember_019f8a43-0458-7fc7-a71c-7f4d55ea7434_terseLabel_en-US" xlink:label="lab_skwd_MiscellaneousFeeIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Miscellaneous fee income</link:label>
    <link:label id="lab_skwd_MiscellaneousFeeIncomeMember_label_en-US" xlink:label="lab_skwd_MiscellaneousFeeIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Miscellaneous Fee Income [Member]</link:label>
    <link:label id="lab_skwd_MiscellaneousFeeIncomeMember_documentation_en-US" xlink:label="lab_skwd_MiscellaneousFeeIncomeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Miscellaneous Fee Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MiscellaneousFeeIncomeMember" xlink:href="skwd-20260630.xsd#skwd_MiscellaneousFeeIncomeMember"/>
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    <link:label id="lab_skwd_SMA2Member_019e3bd8-60c7-7efc-a4bb-70345367fe78_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-20260630.xsd#skwd_SMA2Member"/>
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    <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/2026/ecd-2026.xsd#ecd_InsiderTradingPoliciesProcLineItems"/>
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    <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/2026/elts/us-gaap-2026.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_VariableRateDomain_019e3bd8-6167-7e0f-a4ac-74f32238f71d_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:label id="lab_us-gaap_VariableRateDomain_label_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableRateDomain"/>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_019e3bd8-61f1-7ee5-8828-ade5d3053928_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_019e3bd8-61f1-78b5-8863-87a72765eb6a_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract"/>
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    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_019e3bd8-60c7-745d-8bb2-31a6a358db18_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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward"/>
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    <link:label id="lab_skwd_BusinessCombinationFixedMaturitySecuritiesAvailableForSaleAtFairValue_019e3bd8-6167-7055-a04f-f35b653c96c9_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-20260630.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_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_019e3bd8-60c8-7faf-864f-376bba18e4c8_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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable"/>
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    <link:label id="lab_us-gaap_StatementLineItems_019e3bd8-60c7-7b2f-abe1-0e1c46615259_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>
    <link:label id="lab_us-gaap_StatementLineItems_label_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StatementLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementLineItems" xlink:to="lab_us-gaap_StatementLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Assets_019e3bd8-60c7-717a-9536-469978a3af8d_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/2026/elts/us-gaap-2026.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_EquityMethodInvestmentNonconsolidatedInvesteeDomain_019e3bd8-61f1-76de-a84a-49db4b0d240a_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/2026/elts/us-gaap-2026.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_us-gaap_OperatingSegmentsMember_019e3bd8-6168-7dd5-a7ff-ac73f107bd34_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/2026/elts/us-gaap-2026.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_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_019e3bd8-6167-79d4-a161-03b96b2ade48_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/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_019e3bd8-61f1-7e7e-8a51-304efb6f7459_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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities"/>
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    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential_019e3bd8-60c8-7023-8ddb-8c13172f0a45_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign operations taxed at statutory tax rates</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Foreign Income Tax Rate Differential, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationForeignIncomeTaxRateDifferential"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_019e3bd8-5ff8-7425-89e6-0b437dbfc306_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/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue"/>
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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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PeoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoMember" xlink:to="lab_ecd_PeoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TermLoanCreditFacilityMember_019e3bd8-60c7-73d5-a299-8bd5ba491cef_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:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TermLoanCreditFacilityMember" xlink:to="lab_skwd_TermLoanCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_019e3bd8-60c8-737c-8182-706098bc3d1a_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/2026/elts/us-gaap-2026.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_Goodwill_019e3bd8-60c7-724a-8565-4cdf909f5b77_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_019e3bd8-60c7-7c78-a64c-456e0635f68c_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">Preliminary allocation to 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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions_019e3bd8-6168-71dd-9e27-134e6837a928_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionNumberOfPositions"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable_019e3bd8-6168-7b53-9480-a5237e4bf34b_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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable"/>
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    <link:label id="lab_us-gaap_RetainedEarningsMember_019e3bd8-60c7-7a36-bda2-003e9ce65084_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsMember" xlink:to="lab_us-gaap_RetainedEarningsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_019e3bd8-61f1-7dbb-bd96-61829407bfd1_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/2026/elts/us-gaap-2026.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_FairValueMeasurementPolicyPolicyTextBlock_019e3bd8-60c7-72a0-8aa6-35af4d4b229f_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/2026/elts/us-gaap-2026.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_IncreaseDecreaseInStockholdersEquityRollForward_019e3bd8-6167-7fdf-8e30-1f83f0c46809_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/2026/elts/us-gaap-2026.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_CommonStockSharesOutstanding_019e3bd8-6168-7b06-8b4b-d233a4d1b33d_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_019e3bd8-6168-7653-a6a5-897391412b10_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_019e3bd8-6168-73c9-8cd6-67c1e5bf2c7c_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_us-gaap_CorporateDebtSecuritiesMember_019e3bd8-6167-78ac-ba71-363427e4f81c_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Corporate securities and miscellaneous</link:label>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Corporate Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CorporateDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:to="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_019e3bd8-6168-7277-be63-d1700b73a36b_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/2026/elts/us-gaap-2026.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_019e3bd8-60c7-7fd9-9a11-2cc19524c517_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossRollForward"/>
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    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_019e3bd8-60c7-712d-be78-b3ae0272ef4b_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_019e3bd8-60c7-7255-a733-264b2d5a54e3_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">Intangible Asset, Finite-Lived, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AmortizationOfIntangibleAssets"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems_019e3bd8-6168-76a0-9758-f31b659e206f_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">Intangible Asset, Finite-Lived [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">Intangible Asset, Finite-Lived [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_019e3bd8-6167-74ae-8039-e6fed1ae36f9_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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets"/>
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    <link:label id="lab_us-gaap_PremiumsWrittenNet_019e3bd8-6168-70a7-acc2-8db4a736c8d4_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>
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    <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_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity_019e3bd8-6168-7e60-93fb-bb9d899211d0_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/2026/elts/us-gaap-2026.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_FinitelivedIntangibleAssetsAcquired1_019e3bd8-6168-75f2-8a2d-6db8f8fa16ff_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">Intangible Asset, Finite-Lived, Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_RevenueFromContractWithCustomerExcludingAssessedTax_019e3bd8-6167-793a-b19b-5abad7c3379d_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/2026/elts/us-gaap-2026.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_EquityMethodInvestmentsTextBlock_019e3bd8-61f2-7fd0-9abc-521a713789a6_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/2026/elts/us-gaap-2026.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_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_019e3bd8-60c8-7459-b5f6-dc28a2c5be09_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/2026/elts/us-gaap-2026.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_StockRepurchasedDuringPeriodValue_019fb7a8-26f9-7f73-9aea-36277808e632_terseLabel_en-US" xlink:label="lab_us-gaap_StockRepurchasedDuringPeriodValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock repurchased during period, value</link:label>
    <link:label id="lab_us-gaap_StockRepurchasedDuringPeriodValue_label_en-US" xlink:label="lab_us-gaap_StockRepurchasedDuringPeriodValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Repurchased During Period, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockRepurchasedDuringPeriodValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockRepurchasedDuringPeriodValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockRepurchasedDuringPeriodValue" xlink:to="lab_us-gaap_StockRepurchasedDuringPeriodValue" 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/2026/ecd-2026.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_srt_ShareRepurchaseProgramLineItems_019fcb32-4cd0-76af-8d62-f236d4451ee0_terseLabel_en-US" xlink:label="lab_srt_ShareRepurchaseProgramLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share Repurchase Program [Line Items]</link:label>
    <link:label id="lab_srt_ShareRepurchaseProgramLineItems_label_en-US" xlink:label="lab_srt_ShareRepurchaseProgramLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share Repurchase Program [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ShareRepurchaseProgramLineItems" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ShareRepurchaseProgramLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ShareRepurchaseProgramLineItems" xlink:to="lab_srt_ShareRepurchaseProgramLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_019e3bd8-60c8-76b2-9d3a-56f1d926196f_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 Asset, Excluding Goodwill, before Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IntangibleAssetsGrossExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NumberOfUSSubsidiaries_019e3bd8-61f2-7275-b3f1-553ab8a085c5_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-20260630.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_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_019e3bd8-6168-7e4b-b212-ce29c9c0edc1_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/2026/elts/us-gaap-2026.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_AssumedPremiumsWritten_019e3bd8-60c8-75f3-8856-a6dc22c3f40e_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/2026/elts/us-gaap-2026.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_DebtInstrumentCreditSpreadAdjustment_019e3bd8-61f1-724d-8d66-7b039a823da7_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-20260630.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_skwd_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustmentsAfterAcquisition_019e3bd8-6168-7bb4-84eb-4f11418276d4_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-20260630.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_us-gaap_ScheduleOfEquityMethodInvestmentsTable_019e3bd8-6167-768d-95e8-2598857065b6_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Equity Method Investments [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:to="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ForeignCountryMember_019e3bd8-6168-7360-b755-b08f918471ee_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">Income Tax Jurisdiction, Foreign</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">Income Tax Jurisdiction, Foreign [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignCountryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_skwd_ShortTermInvestmentsAndCashMember_019e3bd8-60c7-77ce-9fc9-0ebf5e25b5e7_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-20260630.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_AmortizationOfDeferredCharges_019e3bd8-60c7-746d-95d1-e7915abdda6f_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_019e3bd8-60c7-7ecd-a3bf-744472d087f7_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>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_RelatedPartyTransactionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionDomain" xlink:to="lab_us-gaap_RelatedPartyTransactionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationDisclosureTextBlock_019e3bd8-6168-7360-8e85-ac0510d234b1_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/2026/elts/us-gaap-2026.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"/>
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    <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-20260630.xsd#skwd_DebtInstrumentCovenantLimitationOnAdditionalIndebtednessMaximumWithADebtBalance"/>
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    <link:label id="lab_us-gaap_ForeignGovernmentDebtSecuritiesMember_019e3bd8-60c7-76d2-9d6e-0e7364cd57a5_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/2026/elts/us-gaap-2026.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"/>
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    <link:label id="lab_ecd_Rule10b51ArrAdoptedFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Adopted [Flag]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrAdoptedFlag" xlink:to="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesMember_019e3bd8-6167-79b4-b97d-96aa1c7b5356_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/2026/elts/us-gaap-2026.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"/>
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    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" 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 [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_019e3bd8-6167-750c-b1e8-5fd29b82857a_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/2026/elts/us-gaap-2026.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_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_019e3bd8-61f1-7afd-824b-4f4ff7c42aca_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_019e3bd8-61f1-7da1-8429-7170fe0abfac_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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019e3bd8-60c7-7002-8fc5-3a21bf6ddfe5_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
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    <link:label id="lab_srt_ProductsAndServicesDomain_019e3bd8-61f1-7202-baf6-d26ffdea3203_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/2026/elts/srt-2026.xsd#srt_ProductsAndServicesDomain"/>
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    <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>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_DisaggregationOfRevenueTable"/>
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    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_019e3bd8-60c7-703f-a25b-6d80bd472a35_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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles_019e3bd8-6168-756e-a40e-a1138718a488_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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibles"/>
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    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate_019e3bd8-60c7-7871-b075-7dfeaa1a3d0e_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/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate"/>
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    <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/2026/ecd-2026.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_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_019e3bd8-6168-79ee-9ca7-a1723f51be57_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/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax_019e3bd8-6167-76bd-9d7c-3f87174584e4_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Foreign currency translation adjustment</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Foreign Currency Translation Adjustment, Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossForeignCurrencyTranslationAdjustmentTax" xlink:type="arc" order="1"/>
    <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>
    <link:label id="lab_ecd_AwardGrantDateFairValue_label_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardGrantDateFairValue" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardGrantDateFairValue" xlink:to="lab_ecd_AwardGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_019e3bd8-60c8-78f4-8fa4-892feeeba34a_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/2026/elts/us-gaap-2026.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_skwd_MortgageLoansMember_019e3bd8-6167-7fcd-a319-78c59662c5f5_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-20260630.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_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/2026/ecd-2026.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_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/2026/ecd-2026.xsd#ecd_TrdArrDuration"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrDuration" xlink:to="lab_ecd_TrdArrDuration" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidationItemsAxis_019e3bd8-5ff8-79af-8dda-b24abc0b5027_terseLabel_en-US" xlink:label="lab_srt_ConsolidationItemsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidation Items [Axis]</link:label>
    <link:label id="lab_srt_ConsolidationItemsAxis_label_en-US" xlink:label="lab_srt_ConsolidationItemsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidation Items [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidationItemsAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ConsolidationItemsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidationItemsAxis" xlink:to="lab_srt_ConsolidationItemsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_019e3bd8-60c7-7bbb-813c-e2efe7ba8f60_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/2026/dei-2026.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_dei_EntityRegistrantName_019e3bd8-6168-7422-83ff-e9560e89f81b_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/2026/dei-2026.xsd#dei_EntityRegistrantName"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019e3bd8-6167-7981-bb3c-46061cf91c0b_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_019e3bd8-6168-7d64-8988-a98d9285791c_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/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsuranceRecoverablesAllowance"/>
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    <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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:to="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_019e3bd8-60c7-75e6-b682-fdddd852b2b9_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">Intangible Asset, Finite-Lived, before Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsGross"/>
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    <link:label id="lab_us-gaap_Revenues_019e3bd8-60c7-7670-9964-08cb331702b7_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>
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    <link:label id="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Expense of Enforcement, Amount</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxAssets"/>
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    <link:label id="lab_us-gaap_GoodwillRollForward_019e3bd8-60c7-7dd7-91af-6578443ca341_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/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillRollForward"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_019e3bd8-6167-7d1f-85e6-84451e3ccdf9_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">Intangible Asset, Finite-Lived, Class [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">Intangible Asset, Finite-Lived, Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain"/>
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    <link:label id="lab_us-gaap_TradeNamesMember_019e3bd8-61f1-7874-8a6f-b050afe8a369_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/2026/elts/us-gaap-2026.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"/>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock"/>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_019e3bd8-60c7-78e7-93cf-308754b03d23_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/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
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    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_019e3bd8-60c7-7dea-9679-a5e86e5930c4_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>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueDisclosuresTextBlock"/>
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    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_019e3bd8-60c8-756f-b4cc-517be14151cc_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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueInputsLevel3Member"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_019e3bd8-6168-7361-b1c0-81e71f3b6688_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>
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    <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">Intangible Asset, Finite-Lived, Estimated Amortization Expense, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths"/>
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    <link:label id="lab_us-gaap_TreasuryStockSharesAcquired_019e3bd8-60c7-72d0-a24a-4588596506f1_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember"/>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_OtherAssets"/>
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    <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-20260630.xsd#skwd_LossOnSaleOfOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LossOnSaleOfOtherInvestments" xlink:to="lab_skwd_LossOnSaleOfOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockValueAcquiredCostMethod_019e3bd8-60c7-7468-81ba-faecc44dd402_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/2026/elts/us-gaap-2026.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_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019e3bd8-6167-757f-8301-18e2dcfb6960_periodStartLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Cash and cash equivalents and restricted cash at beginning of period</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_019e3bd8-6167-7d0d-a7a8-f3e1a8ab4a5b_periodEndLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Cash and cash equivalents and restricted cash at end of period</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash, Cash Equivalent, Restricted Cash, and Restricted Cash Equivalent, Continuing Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued_019f8a1f-b29f-7f19-8cac-a6e71f4a8ca7_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuance of treasury stock</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Issued During Period, Value, Treasury Stock Reissued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueTreasuryStockReissued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_019e3bd8-61f1-7552-bc4d-a85bc12cdcd9_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/2026/elts/us-gaap-2026.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_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets_019e3bd8-5ff8-7a34-9e37-b65d6d995fe7_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Estimated fair value, indefinite-lived</link:label>
    <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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_019e3bd8-61f1-7817-a3bb-00fa558095f1_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/2026/elts/us-gaap-2026.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_ecd_NonNeosMember_terseLabel_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-NEOs</link:label>
    <link:label id="lab_ecd_NonNeosMember_label_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-NEOs [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonNeosMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_NonNeosMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonNeosMember" xlink:to="lab_ecd_NonNeosMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesGross_019e3bd8-61f2-7195-856a-63502f0e678d_verboseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Cash consideration</link:label>
    <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/2026/elts/us-gaap-2026.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_EquityMethodInvestmentOwnershipPercentage_019e3bd8-6168-7016-a677-7471d2090a53_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/2026/elts/us-gaap-2026.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_ReportingUnitDomain_019e3bd8-60c7-7b80-ba4f-e2d0690d0619_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/2026/elts/us-gaap-2026.xsd#us-gaap_ReportingUnitDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReportingUnitDomain" xlink:to="lab_us-gaap_ReportingUnitDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo_019e3bd8-61f1-7f0b-bd20-47c5146de6ca_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">Intangible Asset, Finite-Lived, Estimated Amortization Expense, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium_019e3bd8-60c7-70c8-b5d6-848d58540ed3_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-20260630.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:to="lab_skwd_BusinessCombinationRecognizedAssetAcquiredCededUnearnedPremium" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SpecialtyProgramsMember_019e3bd8-6167-7194-9ebb-f5a1526cf10a_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-20260630.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_019e3bd8-6168-786d-8463-7d25f3b9090b_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-20260630.xsd#skwd_TotalIntangibleAssetsRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TotalIntangibleAssetsRollForward" xlink:to="lab_skwd_TotalIntangibleAssetsRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_019e3bd8-6167-787c-b718-0e6fe602f831_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/2026/elts/srt-2026.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_us-gaap_LongtermDebtTypeDomain_019e3bd8-60c7-74b0-bd15-b727be764f0c_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/2026/elts/us-gaap-2026.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_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_019e3bd8-5ff8-7797-9498-06ce9caa5e48_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/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_019e3bd8-60c7-7cf9-95f0-f17920a1342f_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/2026/elts/us-gaap-2026.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_skwd_ApolloSegmentMember_019e3bd8-60c7-7b41-a1c6-50784d78d85f_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-20260630.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_srt_RangeAxis_019e3bd8-6168-7757-ad1f-5917f53558e2_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/2026/elts/srt-2026.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_AwardTypeAxis_019e3bd8-60c7-7159-87f3-85a3f8d40dcb_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/2026/elts/us-gaap-2026.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_skwd_DebtInstrumentFixedRatePeriodAxis_019e3bd8-61f2-7169-a555-fa463ce9b48c_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-20260630.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_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/2026/ecd-2026.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_RetainedEarningsAccumulatedDeficit_019e3bd8-61f1-713c-9de2-3f6109d54363_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" 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_RetainedEarningsAccumulatedDeficit_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retained Earnings (Accumulated Deficit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:to="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingAgencyFeePercentage_019e3bd8-60c7-747c-b0e4-6eb1638103c1_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-20260630.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_srt_ProductOrServiceAxis_019e3bd8-6167-76c3-ba3e-deb14ab98eb5_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>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductOrServiceAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_ProductOrServiceAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductOrServiceAxis" xlink:to="lab_srt_ProductOrServiceAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_019e3bd8-60c8-7fb9-9d58-8b9eca8c5057_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_019e3bd8-60c8-7068-9e08-8bf7ecd8e296_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/2026/elts/us-gaap-2026.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_skwd_AgentRelationshipMember_019e3bd8-60c8-74c3-9b1d-eba8bd26ae5b_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-20260630.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_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/2026/ecd-2026.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_us-gaap_CommonStockMember_019e3bd8-60c7-740f-8bae-5443e3b60a19_netLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Common stock:</link:label>
    <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/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockMember" xlink:to="lab_us-gaap_CommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember_019e3bd8-61f1-7add-9a83-963c9c4f6c93_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/2026/elts/us-gaap-2026.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_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract_019e3bd8-60c7-7292-b6a3-39eb8fb0d3e6_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Intangible Asset, Finite-Lived, after Accumulated Amortization, Estimated Amortization Expense, Fiscal Year Maturity [Abstract]</link:label>
    <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">Intangible Asset, Finite-Lived, after Accumulated Amortization, Estimated Amortization Expense, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_019e3bd8-6168-7c68-ba80-8a3e25a55beb_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities and stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities and Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_019e3bd8-60c7-79f0-a752-601055bbfc5e_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 Asset, Including Goodwill, after Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_skwd_RelatedPartyOwnershipInterest_019e3bd8-6168-7d3e-8f79-a4dcab6fa2ca_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-20260630.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_EmployeeStockOptionMember_019e3bd8-61f2-7ff5-82b9-7b0b1afaf2af_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/2026/elts/us-gaap-2026.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"/>
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    <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/2026/elts/us-gaap-2026.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_us-gaap_StatementBusinessSegmentsAxis_019e3bd8-6168-7879-a063-8faf656de00e_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_us-gaap_FairValueByAssetClassAxis_019e3bd8-60c7-75bb-be7b-17864e94c6ca_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByAssetClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Class [Axis]</link:label>
    <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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByAssetClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByAssetClassAxis" xlink:to="lab_us-gaap_FairValueByAssetClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyDomain_019e3bd8-61f1-76e1-b3ab-f6985d17df2f_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_AdditionalPaidInCapital_019e3bd8-6168-7914-a3c3-35258fdea8de_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" 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_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/2026/elts/us-gaap-2026.xsd#us-gaap_AdditionalPaidInCapital"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapital" xlink:to="lab_us-gaap_AdditionalPaidInCapital" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_019e3bd8-60c7-79a1-90e4-092930cc0d76_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_019e3bd8-60c7-70e1-aa7a-e46e3be16a3c_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_019e3bd8-60c7-7a65-a3dc-9ebb54d4f278_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/2026/elts/us-gaap-2026.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_skwd_RealizedInvestmentLosses_019e3bd8-60c7-7e8d-a43b-fae919eb6c38_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-20260630.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_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_019e3bd8-6167-7b8c-a45c-f3d0faabbf4b_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-20260630.xsd#skwd_DebtInstrumentFixedInterestRatePeriodTwoMember"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree_019e3bd8-6168-768b-a3e6-a4e8b9785416_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">Intangible Asset, Finite-Lived, Estimated Amortization Expense, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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"/>
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    <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">Intangible Asset, Finite-Lived, Estimated Amortization Expense, 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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.xsd#ecd_AwardsCloseToMnpiDiscIndName"/>
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    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_terseLabel_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested</link:label>
    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_label_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember"/>
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    <link:label id="lab_us-gaap_CededPremiumsWritten_019e3bd8-61f1-7f04-aea7-a63c07d62b01_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/2026/elts/us-gaap-2026.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_skwd_TransactionalESMember_019e3bd8-60c7-7181-b9a9-a45d5ee26b52_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-20260630.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_TradingSecuritiesAndCertainTradingAssetsTextBlock_019e3bd8-60c7-71ec-907c-52700a28e56e_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock"/>
    <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_FinancingReceivablePortfolioSegmentAxis_019e3bd8-6167-7d6a-96ae-cba8bfbca8b0_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_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/2026/ecd-2026.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_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/2026/ecd-2026.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_us-gaap_InterestPaidNet_019e3bd8-6168-7eed-91ff-b318a6aa356c_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/2026/elts/us-gaap-2026.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_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_019e3bd8-6168-7b7d-8be5-4a835b7c9518_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/2026/elts/us-gaap-2026.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_us-gaap_HedgingDesignationAxis_019e3bd8-61f1-781d-944f-5799677d503d_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/2026/elts/us-gaap-2026.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_skwd_CaptivesMember_019e3bd8-61f1-7d89-9528-a4a338deb2b6_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-20260630.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_019e3bd8-6167-7eb9-8d3b-c144f3877f3b_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-20260630.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_CreditFacilityAxis_019e3bd8-60c8-7d6a-8a6f-36524f207b9a_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/2026/elts/us-gaap-2026.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_us-gaap_AssetsFairValueDisclosure_019e3bd8-5ff8-7201-a4d1-093788d7a71e_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_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/2026/ecd-2026.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_FairValueMeasurementsFairValueHierarchyDomain_019e3bd8-6167-73cb-973b-ae33d61089cf_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/2026/elts/us-gaap-2026.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_us-gaap_DebtInstrumentLineItems_019e3bd8-60c7-7700-8bc7-3f64c7c8ea1e_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/2026/elts/us-gaap-2026.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_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_019e3bd8-60c7-7548-aa56-a64693304be0_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_019e3bd8-60c7-7be9-b87e-3b22bb7969fb_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:to="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_019e3bd8-60c7-78b4-8e3d-3d347d0b93b3_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/2026/elts/us-gaap-2026.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_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_019e3bd8-6167-7449-ad69-bdfdf57a1229_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">Intangible Asset, Indefinite-Lived, Class [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">Intangible Asset, Indefinite-Lived, Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_skwd_DowlingCapitalPartnersLPMember_019e3bd8-61f2-71c7-a9c2-77dc9aecb356_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-20260630.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_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/2026/ecd-2026.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_CashAndCashEquivalentsAtCarryingValue_019e3bd8-6168-7ad5-8004-8a7e29e755d5_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" 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_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/2026/elts/us-gaap-2026.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:to="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" 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/2026/ecd-2026.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_EquitySecuritiesFvNiUnrealizedGainLoss_019e3bd8-6168-7a6c-afb8-844469c2ad01_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/2026/elts/us-gaap-2026.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_SecuredOvernightFinancingRateSofrMember_019e3bd8-60c7-7b3f-b82c-8134c0e6852e_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/2026/elts/us-gaap-2026.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_StockIssuedDuringPeriodSharesShareBasedCompensation_019e3bd8-6168-7869-b523-06aca1fd144d_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">(Acquisition) issuance of common stock (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/2026/elts/us-gaap-2026.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_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable_019e3bd8-60c7-75a1-8f70-539905231c18_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounts and Financing Receivables [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:to="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" 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/2026/ecd-2026.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_GainLossOnFairValueHedgesRecognizedInEarnings_019e3bd8-5ff8-7ae1-b09a-23c807df0d75_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/2026/elts/us-gaap-2026.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_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit_019fcdd9-bedd-7876-a422-6b09d77ac8b1_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" 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_InvestmentIncomeOperatingTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income, Operating, Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" xlink:to="lab_us-gaap_InvestmentIncomeOperatingTaxExpenseBenefit" 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/2026/ecd-2026.xsd#ecd_AwardTmgMethodTextBlock"/>
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    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e3bd8-60c7-73d9-a63f-40f21faf5b71_totalLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net increase in cash and cash equivalents and restricted cash</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash, Cash Equivalent, Restricted Cash, and Restricted Cash Equivalent, Period Increase (Decrease), Including Exchange Rate Effect and Discontinued Operation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
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    <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/2026/ecd-2026.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_us-gaap_NetIncomeLoss_019e3bd8-60c7-7147-9fa5-b6e4570da311_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_019e3bd8-60c7-7584-9c91-d87c9d34aa3b_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_019e3bd8-60c7-7428-b1ac-ce4d0aefada8_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/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
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    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_019e3bd8-60c7-740a-9472-07ce0f1eb2ca_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_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/2026/ecd-2026.xsd#ecd_RestatementDateAxis"/>
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    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_019e3bd8-60c7-750d-95e3-f4b8e0d19d37_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/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock"/>
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    <link:label id="lab_skwd_MortgageLoansUncollectableWriteOff_019e3bd8-60c7-7e49-adee-06064299b6d2_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-20260630.xsd#skwd_MortgageLoansUncollectableWriteOff"/>
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    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilitiesAbstract_019e3bd8-60c7-7d23-a71e-b19cbbb96ba5_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>
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    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_019e3bd8-6168-70c2-8581-4edb7326f0a6_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/2026/elts/us-gaap-2026.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_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_019e3bd8-61f1-702f-90b0-6ff461bc2f9d_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_019e3bd8-61f1-7cf0-81ce-4752df3b7b30_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/2026/elts/us-gaap-2026.xsd#us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:to="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_019e3bd8-61f1-76eb-82a3-fae84b8e2428_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.xsd#ecd_PnsnBnftsAdjFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnBnftsAdjFnTextBlock" xlink:to="lab_ecd_PnsnBnftsAdjFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_019e3bd8-60c7-779f-b6b5-27d4cdac6f2c_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">Intangible Asset 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">Intangible Asset 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/2026/elts/us-gaap-2026.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_srt_RangeMember_019e3bd8-60c7-705e-8a3a-3a4269457cd6_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/2026/elts/srt-2026.xsd#srt_RangeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeMember" xlink:to="lab_srt_RangeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsEarned_019e3bd8-5ff8-77ba-9a20-53a0ba0a8620_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/2026/elts/us-gaap-2026.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_dei_DocumentFiscalYearFocus_019e3bd8-5ff8-74ff-b5d7-cdabd86b3943_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/2026/dei-2026.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_BusinessCombinationAcquisitionRelatedCosts_019f36af-b8e8-7b7d-9bad-ed2b5b6cf28c_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Material transaction expenses</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationAcquisitionRelatedCosts_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Acquisition-Related Cost, Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationAcquisitionRelatedCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:to="lab_us-gaap_BusinessCombinationAcquisitionRelatedCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember_019e3bd8-6168-738c-af37-1eb809bb8b17_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>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:href="skwd-20260630.xsd#skwd_CashAndCashEquivalentsAndOtherAssetsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:to="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_019e3bd8-60c7-7a08-94c5-6d42b755844b_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-20260630.xsd#skwd_FixedMaturitySecuritiesAvailableForSaleMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:to="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockValue_019e3bd8-60c8-7107-af51-b09fcbce8163_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, 44,827,499 shares issued and 44,396,493 shares outstanding at June&#160;30, 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/2026/elts/us-gaap-2026.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_InterestExpense_019e3bd8-6167-7fd7-9b3f-cc670659c15e_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/2026/elts/us-gaap-2026.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_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables_019e3bd8-61f2-7e55-8775-afb77b2b06af_terseLabel_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" 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_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables_label_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Reinsurance And Premium Payables</link:label>
    <link:label id="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables_documentation_en-US" xlink:label="lab_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Business Combination, Recognized Liability Assumed, Reinsurance And Premium Payables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables" xlink:href="skwd-20260630.xsd#skwd_BusinessCombinationRecognizedLiabilityAssumedReinsuranceAndPremiumPayables"/>
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    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_019e3bd8-6167-71fe-b3af-b1d009841bc2_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/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfDebtInstrumentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:to="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery_019e3bd8-61f1-7abe-8c1a-15b910777dee_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAllowanceForCreditLossRecovery"/>
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    <link:label id="lab_us-gaap_LineOfCreditMember_019e3bd8-61f2-7285-8f9a-aa694c288c74_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of Credit</link:label>
    <link:label id="lab_us-gaap_LineOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LineOfCreditMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditMember" xlink:to="lab_us-gaap_LineOfCreditMember" 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/2026/ecd-2026.xsd#ecd_RestatementDeterminationDate"/>
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    <link:label id="lab_dei_AmendmentFlag_019e3bd8-61f2-77e8-b610-a9082f9d239e_terseLabel_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amendment Flag</link:label>
    <link:label id="lab_dei_AmendmentFlag_label_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amendment Flag</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AmendmentFlag" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_AmendmentFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_AmendmentFlag" xlink:to="lab_dei_AmendmentFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2025Member_019e3bd8-60c7-77cb-993d-59b8204b1e52_terseLabel_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2025Member_label_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2025 [Member]</link:label>
    <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-20260630.xsd#skwd_RevolvingLineOfCreditDueDecember2025Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:to="lab_skwd_RevolvingLineOfCreditDueDecember2025Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetInvestmentIncome_019e3bd8-60c7-7c47-a12c-73ed65b12455_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_019e3bd8-60c7-754e-9e52-7455126c6b2a_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/2026/elts/us-gaap-2026.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_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_019e3bd8-60c7-790a-baa6-eb916b56c98e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" 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_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Accumulated Gross Unrealized Loss, before Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_019e3bd8-6168-7a78-96b3-3e7bf10b0b0c_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_019e3bd8-6168-7628-92d8-52eaebbffc51_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>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_label_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indirect Loans and Loan Collateral [Member]</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_documentation_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Indirect Loans and Loan Collateral</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IndirectLoansAndLoanCollateralMember" xlink:href="skwd-20260630.xsd#skwd_IndirectLoansAndLoanCollateralMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IndirectLoansAndLoanCollateralMember" xlink:to="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_019e3bd8-61f1-790f-af29-f51a97eb53b8_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/2026/elts/us-gaap-2026.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_FederalHomeLoanBankAdvancesMember_019e3bd8-6167-7992-8c3d-a7ef6a39d4d4_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3_019e3bd8-6167-7646-b7f1-bb5ce1460b0f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Transfers into Level 3</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" 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 Transfers Into Level 3</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetTransfersIntoLevel3" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressStateOrProvince_019e3bd8-60c7-7251-84f6-ba755fb65c3b_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/2026/dei-2026.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_PaymentsToAcquireEquitySecuritiesFvNi_019e3bd8-60c7-7c99-acf1-ed8a38a6c9be_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_019e3bd8-61f1-766b-be68-49f7bb6da34e_terseLabel_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:label id="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_label_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses [Text Block]</link:label>
    <link:label id="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_documentation_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:href="skwd-20260630.xsd#skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:to="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_019e3bd8-6167-709c-988b-ced887cc6ea4_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_019e3bd8-6167-7843-a146-ca02eb563529_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/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommissionsPolicy_019e3bd8-6167-77d9-8331-e3b0d623158a_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/2026/elts/us-gaap-2026.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_GoodwillImpairedAccumulatedImpairmentLoss_019e3bd8-60c7-7cf9-abbc-6677239f8fe2_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/2026/elts/us-gaap-2026.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_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock_019e3bd8-61f1-7a61-a513-4171205c1594_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/2026/elts/us-gaap-2026.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_DepositContractsAssets_019e3bd8-6167-7ea0-844d-a5064eeb08ca_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/2026/elts/us-gaap-2026.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"/>
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    <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>
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    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensationForfeited_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensationForfeited" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shares Issued, Value, Share-Based Payment Arrangement, Forfeited</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensationForfeited" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockIssuedDuringPeriodValueShareBasedCompensationForfeited"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock" 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 [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleAllowanceForCreditLossTableTextBlock"/>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsAbstract"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_019e3bd8-6168-74da-b210-d517a1e17a11_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue"/>
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    <link:label id="lab_us-gaap_NoninterestIncome_019e3bd8-6168-72fd-a95b-3fe1b9059826_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/2026/elts/us-gaap-2026.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_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract_019e3bd8-6168-7314-baca-e28c4b015df2_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" 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_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract"/>
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    <link:label id="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock_019e3bd8-6168-7bae-b2ac-51422ce4e6aa_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/2026/elts/us-gaap-2026.xsd#us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock"/>
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    <link:label id="lab_ecd_AwardTmgMnpiDiscTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiDiscTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardTmgMnpiDiscTextBlock"/>
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    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_019e3bd8-6167-7201-98f0-566a959cf68c_terseLabel_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basis of Presentation</link:label>
    <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>
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    <link:label id="lab_us-gaap_FairValueHedgeAssetsAtFairValue_019e3bd8-6167-7b1d-8277-2d0541b762f3_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueHedgeAssetsAtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Options, at fair value</link:label>
    <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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueHedgeAssetsAtFairValue"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_019e3bd8-6167-7eeb-82c9-385ff16c3b12_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Accumulated amortization</link:label>
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    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_019e3bd8-60c8-75f4-8880-3f7a06bc3408_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">Intangible Asset, Indefinite-Lived, Acquired</link:label>
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    <link:label id="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock_019e3bd8-6167-707d-89ed-b7d860a5bc78_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>
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    <link:label id="lab_skwd_ManagingAgentsFeesMember_019e3bd8-60c7-7d2b-80c9-55d74f8786a5_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-20260630.xsd#skwd_ManagingAgentsFeesMember"/>
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    <link:label id="lab_us-gaap_TreasuryStockValue_019e3bd8-60c7-7e2b-b6bf-7f63b7aaa8aa_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, 431,006 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/2026/elts/us-gaap-2026.xsd#us-gaap_TreasuryStockValue"/>
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    <link:label id="lab_us-gaap_UnsecuredDebtMember_019e3bd8-6167-792c-83ea-fab6cf4df035_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/2026/elts/us-gaap-2026.xsd#us-gaap_UnsecuredDebtMember"/>
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    <link:label id="lab_skwd_ProfessionalLinesMember_019e3bd8-60c7-7519-9542-d42932937654_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-20260630.xsd#skwd_ProfessionalLinesMember"/>
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    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_019e3bd8-6167-7ac0-85b1-545e29ae4a90_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-20260630.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember"/>
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    <link:label id="lab_us-gaap_OtherAggregatedInvestmentsMember_019e3bd8-60c7-73b9-ba71-2ce4efd87f58_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_OtherAggregatedInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Security Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAggregatedInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherAggregatedInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAggregatedInvestmentsMember" xlink:to="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax_019e3bd8-60c7-7c2c-8a87-11b4f541df37_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/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e3bd8-60c7-7825-87ef-3f8e9f28f986_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 investing 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/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
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    <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/2026/ecd-2026.xsd#ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember"/>
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    <link:label id="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock_019e3bd8-60c7-7830-949a-16b86b6200cf_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stockholders' Equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquityNoteDisclosureTextBlock"/>
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    <link:label id="lab_us-gaap_CostsAndExpensesAbstract_019e3bd8-5ff8-771c-a161-19120cf121c4_terseLabel_en-US" xlink:label="lab_us-gaap_CostsAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Expenses:</link:label>
    <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>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CostsAndExpensesAbstract" xlink:to="lab_us-gaap_CostsAndExpensesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_SecurityExchangeName_019e3bd8-6167-7ac8-bbbd-ab9271f1a9c1_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/2026/dei-2026.xsd#dei_SecurityExchangeName"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss_019e3bd8-60c8-7db5-8100-a17175856e5c_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
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    <link:label id="lab_us-gaap_PremiumsWrittenGross_019e3bd8-61f1-7c9a-8494-5f4712ca3dc9_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/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsWrittenGross"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_019e3bd8-6168-7136-91b9-5aeef66f211d_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" 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_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" 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</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
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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>
    <link:label id="lab_ecd_OutstandingRecoveryIndName_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_OutstandingRecoveryIndName"/>
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    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_019e3bd8-60c7-7332-9809-8427f3664c16_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>
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    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_019e3bd8-6167-7afb-af0b-5e52b055906d_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_019e3bd8-6167-7833-a5f5-d3f9d8f4f48e_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">Intangible Asset, Excluding Goodwill, Indefinite-Lived</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_skwd_OtherSectorsMember_019e3bd8-60c7-70ff-a4e2-2f952e2d524e_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-20260630.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_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/2026/ecd-2026.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_skwd_DeferredCedingCommission_019e3bd8-6168-7ff7-8da0-fc8bd75fee31_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-20260630.xsd#skwd_DeferredCedingCommission"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredCedingCommission" xlink:to="lab_skwd_DeferredCedingCommission" 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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PnsnAdjsPrrSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_PnsnAdjsPrrSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PnsnAdjsPrrSvcCstMember" xlink:to="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract_019e3bd8-60c7-71b1-bd06-d05626dd3fe3_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/2026/elts/us-gaap-2026.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_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue_019e3bd8-6168-7b22-8e1c-867949d5677c_totalLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" 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_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Unrealized Loss Position, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_019e3bd8-61f2-7dee-8e06-b3eac51706f5_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/2026/elts/us-gaap-2026.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_DebtInstrumentCarryingAmount_019eda92-08d8-796a-9b36-ac3b8fc89219_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Long-term debt, gross</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/2026/elts/us-gaap-2026.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_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain_019e3bd8-60c7-7859-942a-f81000236d1a_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/2026/elts/us-gaap-2026.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_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.xsd#ecd_OutstandingRecoveryCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryCompAmt" xlink:to="lab_ecd_OutstandingRecoveryCompAmt" 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/2026/ecd-2026.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_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired_019e3bd8-6168-7ab4-bba7-13f70b3a9674_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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:to="lab_us-gaap_BusinessAcquisitionPercentageOfVotingInterestsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019e3bd8-60c8-7bdd-a5c8-e972ab1b825a_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_019e3bd8-60c8-754a-81e6-bfcbd862eb86_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/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:to="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_019e3bd8-6167-7313-9000-b7255b90154e_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/2026/elts/us-gaap-2026.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_AccountsNotesAndLoansReceivableLineItems_019e3bd8-60c7-75b9-b916-f556b7292f36_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/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsNotesAndLoansReceivableLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:to="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_019e3bd8-60c8-7107-bc5b-e18f8978183a_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/2026/dei-2026.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_RelatedPartyTransactionLineItems_019e3bd8-6167-7a37-a227-5b64d3aa0bac_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/2026/elts/us-gaap-2026.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"/>
    <link:label id="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount_019e3bd8-60c7-7f21-951d-1e9f3969aa16_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/2026/elts/us-gaap-2026.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_ScheduleOfCededCreditRiskByReinsurerTextBlock_019e3bd8-6167-75be-bd95-1bc2bf1bd87d_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Ceded Credit Risk</link:label>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:to="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:type="arc" order="1"/>
    <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/2026/ecd-2026.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_ProceedsFromLinesOfCredit_019e3bd8-6168-7485-bc48-27ef6f96529c_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/2026/elts/us-gaap-2026.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_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock_019e3bd8-61f1-7721-ab3b-c7f5090213f6_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/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:to="lab_us-gaap_DerivativeInstrumentsAndHedgingActivitiesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss_019e3bd8-61f1-757d-9298-6835a73618af_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/2026/elts/us-gaap-2026.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_us-gaap_MortgageReceivablesMember_019e3bd8-6168-779c-9ac9-4001bf612319_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/2026/elts/us-gaap-2026.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_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/2026/elts/us-gaap-2026.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_skwd_GrossRealizedInvestmentGainsAbstract_019e3bd8-5ff8-75f1-a703-331db69ded82_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-20260630.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_TreasuryStockCommonMember_019e3bd8-60c8-7c70-8867-95f6d629096d_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/2026/elts/us-gaap-2026.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_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Asset, Goodwill and Other [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_019e3bd8-61f1-7757-a9e6-e05bf720dde8_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/2026/elts/us-gaap-2026.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_skwd_LoansReceivableMeasurementInput_019e3bd8-60c7-750f-81c5-f2d2e7bb99cf_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-20260630.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_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_019e3bd8-60c7-71eb-a85f-fa50f7b978d7_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">Intangible Asset, Indefinite-Lived, Class [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">Intangible Asset, Indefinite-Lived, Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_019e3bd8-6168-7713-944d-2ca40f8ded0d_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-20260630.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_DerivativeAssetNotionalAmount_019e3bd8-6168-7fde-8295-7dd1fc2dcdd2_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_USGovernmentDebtSecuritiesMember_019e3bd8-61f1-7af7-8809-228890bfa75f_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/2026/elts/us-gaap-2026.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_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>
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    <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_BusinessAcquisitionLineItems_019e3bd8-60c7-757f-83c3-b06ab896fb31_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/2026/elts/us-gaap-2026.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_CommonStockSharesAuthorized_019e3bd8-60c7-7c0a-8274-38be6cfed599_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/2026/elts/us-gaap-2026.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_BrewerLaneVenturesFundIILPMember_019e3bd8-60c7-77f2-aeb5-1ed0b8dd8e75_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-20260630.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_FiniteLivedIntangibleAssetUsefulLife_019e3bd8-6167-7d43-9b4c-dc69723527ff_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">Intangible Asset, Finite-Lived, Useful Life</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_019e3bd8-60c8-7268-924b-ee962c397200_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/2026/elts/us-gaap-2026.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_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_019e3bd8-61f1-7020-98db-b77a141516f7_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/2026/elts/us-gaap-2026.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_skwd_SkywardSpecialtySegmentMember_019e3bd8-60c7-784d-9927-dab5135151f2_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-20260630.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_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/2026/ecd-2026.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_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss_019e3bd8-60c7-7016-a8e1-316d6f9e968c_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $2,256 and $468, respectively)</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_019e3bd8-60c7-763c-ae1d-903e1cf3e1ad_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/2026/elts/us-gaap-2026.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_us-gaap_SegmentReportingInformationLineItems_019e3bd8-60c7-76d8-93c8-0c0fe92301f1_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 [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 [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingInformationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_srt_StockRepurchaseProgramAuthorizedAmount1_019fb7a1-776c-7dde-a38b-5526c32378c0_terseLabel_en-US" xlink:label="lab_srt_StockRepurchaseProgramAuthorizedAmount1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share repurchase program, authorized, amount</link:label>
    <link:label id="lab_srt_StockRepurchaseProgramAuthorizedAmount1_label_en-US" xlink:label="lab_srt_StockRepurchaseProgramAuthorizedAmount1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share Repurchase Program, Authorized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StockRepurchaseProgramAuthorizedAmount1" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_StockRepurchaseProgramAuthorizedAmount1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StockRepurchaseProgramAuthorizedAmount1" xlink:to="lab_srt_StockRepurchaseProgramAuthorizedAmount1" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_019e3bd8-60c7-7cf4-a725-f64c4f172ae3_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-20260630.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_dei_DocumentQuarterlyReport_019e3bd8-6167-7a4a-b523-82b935b146c7_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>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentQuarterlyReport" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentQuarterlyReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentQuarterlyReport" xlink:to="lab_dei_DocumentQuarterlyReport" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnderwritingIncomeNet_019e3bd8-6167-7733-8553-a8c088096d53_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-20260630.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_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/2026/ecd-2026.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_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_019e3bd8-60c7-7741-8489-ae74653993a5_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/2026/elts/us-gaap-2026.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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_019e3bd8-60c7-778a-8c5d-d6340ce19d97_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/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_019e3bd8-6168-7eda-ac84-03460bb6de75_terseLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underwriting, acquisition and insurance expenses</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_019e3bd8-6168-76a1-8730-6c23fc6e84b1_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-20260630.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_RepaymentsOfLongTermDebt_019e3bd8-60c7-79bd-b48c-2f2043f6224f_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Payments on long term borrowings</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_019f36a7-04da-7670-82e1-9758ea4c2c95_verboseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Repayments of long-term debt</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Repayments of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RepaymentsOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:to="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:type="arc" order="1"/>
    <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/2026/ecd-2026.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_EquityMethodInvestments_019e3bd8-6167-79d0-a488-b196df262575_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_019e3bd8-6167-7a66-aa22-0950c314ebba_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_019e3bd8-6167-70b0-8987-d54bb4092fe5_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/2026/elts/us-gaap-2026.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_skwd_RealizedInvestmentGains_019e3bd8-6167-7cbd-8f9d-3ef4eb3d75ee_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-20260630.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_us-gaap_EquityComponentDomain_019e3bd8-60c7-7c2e-b327-6f16f2381eb3_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/2026/elts/us-gaap-2026.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_us-gaap_DeferredPolicyAcquisitionCosts_019e3bd8-6167-7841-853f-38dae65727b0_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" 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_us-gaap_DeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_019e3bd8-61f2-7e06-9445-2648da1f7aa8_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) gains 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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_019e3bd8-5ff8-70b0-9461-a0ef62c44a28_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_MeasurementInputTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeDomain" xlink:to="lab_us-gaap_MeasurementInputTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_019e3bd8-60c7-7d86-be65-b012d232040e_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-20260630.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_LoansReceivableFairValueDisclosure_019e3bd8-60c7-70b5-86b4-fd1b2faea148_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/2026/elts/us-gaap-2026.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_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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrAdoptionDate" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrAdoptionDate"/>
    <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"/>
    <link:label id="lab_skwd_CoverHolderRelationshipsMember_019e3bd8-60c7-7928-b74e-bac94ebbb2ae_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-20260630.xsd#skwd_CoverHolderRelationshipsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CoverHolderRelationshipsMember" xlink:to="lab_skwd_CoverHolderRelationshipsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_019e3bd8-6168-71f3-8994-558ea094aef4_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-20260630.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_019e3bd8-6167-7fa5-90fa-1c5a3822776c_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/2026/elts/srt-2026.xsd#srt_RepurchaseAgreementCounterpartyNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:to="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:type="arc" order="1"/>
    <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>
    <link:label id="lab_ecd_TrdArrIndTitle_label_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Title</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndTitle" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_TrdArrIndTitle"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndTitle" xlink:to="lab_ecd_TrdArrIndTitle" 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/2026/ecd-2026.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_skwd_RISCOMMember_019e3bd8-6168-7cf0-b3bb-6a9734e892d8_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-20260630.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_DirectPremiumsWritten_019e3bd8-60c8-736c-a8d9-41dbbe34538b_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/2026/elts/us-gaap-2026.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_us-gaap_AccountingPoliciesAbstract_label_en-US" xlink:label="lab_us-gaap_AccountingPoliciesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounting Policies [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountingPoliciesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountingPoliciesAbstract"/>
    <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_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/2026/ecd-2026.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_HeldToMaturitySecuritiesFairValue_019e3bd8-60c8-781f-b8c2-1666a50b4baf_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_019e3bd8-60c8-7918-b752-375c46a89f68_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/2026/elts/us-gaap-2026.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_skwd_CreditSpreadAdjustmentMember_019e3bd8-6167-7899-bedf-b154b0a638b4_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-20260630.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_ecd_InsiderTrdPoliciesProcAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted</link:label>
    <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/2026/ecd-2026.xsd#ecd_InsiderTrdPoliciesProcAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:to="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_019e3bd8-6168-7d86-be23-91f4c7bfe67c_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-20260630.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialPortfolioSegmentMember_019e3bd8-6167-7375-98ef-7b11d352a601_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/2026/elts/us-gaap-2026.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_us-gaap_DerivativeInstrumentsGainLossLineItems_019e3bd8-61f1-73ed-8657-183f23193a6e_terseLabel_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Derivative Instruments, Gain (Loss) [Line Items]</link:label>
    <link:label id="lab_us-gaap_DerivativeInstrumentsGainLossLineItems_label_en-US" xlink:label="lab_us-gaap_DerivativeInstrumentsGainLossLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Derivative Instruments, Gain (Loss) [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DerivativeInstrumentsGainLossLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DerivativeInstrumentsGainLossLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DerivativeInstrumentsGainLossLineItems" xlink:to="lab_us-gaap_DerivativeInstrumentsGainLossLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_019e3bd8-6168-7623-a928-72189292c662_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/2026/elts/us-gaap-2026.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_BusinessAcquisitionAcquireeDomain_019e3bd8-6168-77ec-8da2-1187e5cc58ab_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/2026/elts/us-gaap-2026.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_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_019e3bd8-6167-7e0f-a3c6-5e510559003b_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/2026/elts/us-gaap-2026.xsd#us-gaap_CommitmentsAndContingenciesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" 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/2026/ecd-2026.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_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_019e3bd8-60c7-7b89-9fbc-90abd840c594_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/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock"/>
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    <link:label id="lab_srt_WeightedAverageMember_019e3bd8-60c7-7b9f-8ea8-0d956554cc81_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/2026/elts/srt-2026.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_ecd_AllAdjToCompMember_terseLabel_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation</link:label>
    <link:label id="lab_ecd_AllAdjToCompMember_label_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllAdjToCompMember" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AllAdjToCompMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllAdjToCompMember" xlink:to="lab_ecd_AllAdjToCompMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CorporateNonSegmentMember_019e3bd8-5ff8-79a4-aaa4-4391edadcbfc_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/2026/elts/us-gaap-2026.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_us-gaap_BusinessAcquisitionAxis_019e3bd8-6168-7cda-99e7-18bf8de4d973_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/2026/elts/us-gaap-2026.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_NetCashProvidedByUsedInOperatingActivities_019e3bd8-6168-7259-a454-ebd7a45cac4d_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/2026/elts/us-gaap-2026.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_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_019e3bd8-6167-7124-8a83-9efc5df79eca_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-20260630.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_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_019e3bd8-60c7-7a15-9516-216802f49164_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GlobalAndPropertyMember_019e3bd8-6168-76c9-a238-6da6aa73f570_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-20260630.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_IncomeStatementAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Statement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeStatementAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementAbstract" xlink:to="lab_us-gaap_IncomeStatementAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentTransitionReport_019e3bd8-60c7-7345-82e5-cc06ff43598f_terseLabel_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Transition Report</link:label>
    <link:label id="lab_dei_DocumentTransitionReport_label_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Transition Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentTransitionReport" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentTransitionReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentTransitionReport" xlink:to="lab_dei_DocumentTransitionReport" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019e3bd8-6167-76ec-aa2f-2d8691401465_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 (losses) gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019e3bd8-6167-7c0d-96ae-bea0901ff173_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 (losses) gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_019e3bd8-6167-76bf-8c73-1d4e4f654a94_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/2026/elts/us-gaap-2026.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_skwd_NumberOfMortgageLoansNotProducingIncome_019e3bd8-6167-7a53-9bc4-0ddaf4263df8_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-20260630.xsd#skwd_NumberOfMortgageLoansNotProducingIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:to="lab_skwd_NumberOfMortgageLoansNotProducingIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_019e3bd8-6167-75a8-96d4-934955387976_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/2026/elts/us-gaap-2026.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_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/2026/elts/us-gaap-2026.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_dei_CityAreaCode_019e3bd8-61f2-797f-b37d-507bbebcf254_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/2026/dei-2026.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_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/2026/ecd-2026.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_NonGaapMeasureDescriptionTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description</link:label>
    <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/2026/ecd-2026.xsd#ecd_NonGaapMeasureDescriptionTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:to="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue_019e3bd8-60c7-7be0-b810-da5816df34ed_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-20260630.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_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems_019e3bd8-6168-7dc6-b20f-8457c4338abb_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/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_019e3bd8-6167-77b9-bef2-afa6bf818ed2_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/2026/elts/us-gaap-2026.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_skwd_Syndicate1971DigitalEconomyMember_019e3bd8-5ff8-72da-8c77-550b650cbb89_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-20260630.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_PaymentsForProceedsFromShortTermInvestments_019e3bd8-60c7-7f3e-971f-012d80cf82e0_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/2026/elts/us-gaap-2026.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_skwd_JVMFundsLLCMember_019e3bd8-61f2-7edf-ac7c-1761ea4afd76_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-20260630.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_skwd_DebtInstrumentInterestRateFloor_019e3bd8-6167-77a4-a8a8-06e3d5b6750f_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-20260630.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_FairValueByMeasurementBasisAxis_019e3bd8-6167-7db9-9408-9371695bd750_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Basis [Axis]</link:label>
    <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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueByMeasurementBasisAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:to="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_019e3bd8-6168-77c8-9ac4-4d9d65c727b1_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/2026/elts/us-gaap-2026.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_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems_019e3bd8-6167-7713-8aa7-8127d075c6ff_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/2026/elts/us-gaap-2026.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_us-gaap_ReportingUnitAxis_019e3bd8-6167-7123-83d1-4dd47797c71d_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/2026/elts/us-gaap-2026.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_Investments_019e3bd8-60c8-79c9-8cf2-1103b87d15da_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>
    <link:label id="lab_us-gaap_Investments_label_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Investments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Investments" xlink:to="lab_us-gaap_Investments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_019e3bd8-6168-7711-b6a5-012f502c55fe_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/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_019fcb32-4cd0-78f7-a788-e62c829a11ee_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SubsequentEventTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeDomain" xlink:to="lab_us-gaap_SubsequentEventTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CreditAndSuretyMember_019e3bd8-6168-750f-9ee4-90edce6bef3b_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_019e3bd8-6168-7ef0-b439-a55f1021f3c0_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-20260630.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_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_019e3bd8-61f2-7360-b142-15b14593bbab_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/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents" 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/2026/ecd-2026.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_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_019e3bd8-61f1-7c16-9663-b9acc5875b95_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>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCurrentReportingStatus_019e3bd8-60c7-7c1e-90b9-ad2bcdfa06e3_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/2026/dei-2026.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_NetCashProvidedByUsedInFinancingActivities_019e3bd8-5ff8-7574-8720-22c6398c9e63_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock_019e3bd8-6168-7e63-99d8-c38fc6927890_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Fair Value of Consideration Transferred</link:label>
    <link:label id="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock" xlink:to="lab_us-gaap_ScheduleOfBusinessAcquisitionsByAcquisitionTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityAmortizedCostBeforeAllowanceForCreditLoss_019e3bd8-60c7-70d4-998d-146fe4e7f494_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/2026/elts/us-gaap-2026.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_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_019e3bd8-6168-76e4-9d3b-c64e32a4c268_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-20260630.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_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_019e3bd8-61f1-7d85-876c-8db36a97b757_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/2026/elts/us-gaap-2026.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_019e3bd8-6168-7263-859f-422a375b3901_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from financing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" 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 [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AccidentAndHealthMember_019e3bd8-60c7-798b-8403-5ea53f8e2f85_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-20260630.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_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage_019e3bd8-6168-7dd8-9458-d1e7b85ee0c9_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/2026/elts/us-gaap-2026.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_SharesIssuedPricePerShare_019e3bd8-60c7-7339-a9fb-6f48d5ad4077_terseLabel_en-US" xlink:label="lab_us-gaap_SharesIssuedPricePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Shares issued, price per share (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_SharesIssuedPricePerShare_019e3bd8-60c7-75c3-8431-1ec2190bffe1_verboseLabel_en-US" xlink:label="lab_us-gaap_SharesIssuedPricePerShare" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Skyward Specialty Insurance Group, Inc. closing stock price on December 31, 2025 (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_SharesIssuedPricePerShare_label_en-US" xlink:label="lab_us-gaap_SharesIssuedPricePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shares Issued, Price Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharesIssuedPricePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SharesIssuedPricePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SharesIssuedPricePerShare" xlink:to="lab_us-gaap_SharesIssuedPricePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_019e3bd8-60c7-7114-a878-0f423505a079_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/2026/elts/us-gaap-2026.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_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_019e3bd8-61f1-7fc7-86c2-6aedc99bf7d6_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/2026/elts/us-gaap-2026.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_skwd_TermLoanDueAugust2029Member_019e3bd8-6168-77af-b96f-079be3c2b92b_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-20260630.xsd#skwd_TermLoanDueAugust2029Member"/>
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    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_019e3bd8-6168-7de8-9abf-d45aec273f83_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_019e3bd8-6168-7ea9-88ec-f306706f014d_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/2026/elts/us-gaap-2026.xsd#us-gaap_PrepaidReinsurancePremiums"/>
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    <link:label id="lab_skwd_MortgageLoansUnrealizedGainLoss_019e3bd8-60c7-7ee5-92b5-98225adf2b6f_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-20260630.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_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossRecovery_019e3bd8-60c8-757f-be58-2f6287583150_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/2026/elts/us-gaap-2026.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_skwd_PlatformPartnerSyndicatesMember_019e3bd8-60c8-768a-9636-a927b1d8b93b_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-20260630.xsd#skwd_PlatformPartnerSyndicatesMember"/>
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    <link:label id="lab_us-gaap_OtherIncome_019e3bd8-6168-7ab2-8478-791328636f82_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_019e3bd8-6168-7092-920a-4dfaa5ed60ae_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/2026/elts/us-gaap-2026.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_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_019e3bd8-60c8-7e87-928b-baa866f43564_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">Intangible Asset, Finite-Lived, 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">Intangible Asset, Finite-Lived, Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_019e3bd8-60c7-7a4f-a173-30ca70960238_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">Intangible Asset and Goodwill [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardUndrlygSecuritiesAmt" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_AwardUndrlygSecuritiesAmt"/>
    <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_EstimateOfFairValueFairValueDisclosureMember_019e3bd8-6167-7e7a-9703-d2e71cdaa3ad_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/2026/elts/us-gaap-2026.xsd#us-gaap_EstimateOfFairValueFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:to="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_019e3bd8-6167-77e7-9605-5715995ea532_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/2026/elts/us-gaap-2026.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_PreferredStockMember_019e3bd8-60c8-71fd-af3c-6e7cc28f848f_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/2026/elts/us-gaap-2026.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_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff_019e3bd8-6167-7693-a9e3-1f56ef6244e6_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Write-offs</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff" 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, Writeoff</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterestAllowanceForCreditLossWriteoff" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagedSyndicatesMember_019e3bd8-6168-74b3-88da-dec94c039b77_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-20260630.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_skwd_RetailPortfolioSegmentMember_019e3bd8-6167-79a1-a527-9a8ebccfea2c_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-20260630.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_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable_019e3bd8-6167-7f72-b9a6-7dab48bc7f96_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">Segment Reporting [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">Segment Reporting [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable_019e3bd8-60c8-7081-b090-cdb770a64ab9_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:to="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual_019fd87a-b56d-748e-b32e-232e592067db_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revenue since acquisition date</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Acquiree's Revenue since Acquisition Date, Actual</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual" xlink:to="lab_us-gaap_BusinessCombinationProFormaInformationRevenueOfAcquireeSinceAcquisitionDateActual" 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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_019e3bd8-6168-78eb-a5b5-15e6001c39d0_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/2026/elts/us-gaap-2026.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" 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/2026/ecd-2026.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_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/2026/ecd-2026.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_skwd_ArenaSpecialOpportunitiesFundLPMember_019e3bd8-6167-7adb-93a2-ff43df57486f_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-20260630.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_dei_CurrentFiscalYearEndDate_019e3bd8-6168-75cf-ab20-1bb43fb33708_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/2026/dei-2026.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_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/2026/ecd-2026.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_StockRepurchasedDuringPeriodShares_019fb7a8-26f9-7e38-af45-2295cc824f28_terseLabel_en-US" xlink:label="lab_us-gaap_StockRepurchasedDuringPeriodShares" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock repurchased during period (in shares)</link:label>
    <link:label id="lab_us-gaap_StockRepurchasedDuringPeriodShares_label_en-US" xlink:label="lab_us-gaap_StockRepurchasedDuringPeriodShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Repurchased During Period, Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockRepurchasedDuringPeriodShares" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockRepurchasedDuringPeriodShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockRepurchasedDuringPeriodShares" xlink:to="lab_us-gaap_StockRepurchasedDuringPeriodShares" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnrecordedUnconditionalPurchaseObligationBalanceSheetAmount_019e3bd8-60c7-7aa5-8ad0-e7d51702d835_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.xsd#ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:to="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFileNumber_019e3bd8-6167-70a2-9544-8dbc00933c51_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/2026/dei-2026.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_skwd_VariableInterestEntityAbstract_019e3bd8-61f1-738e-8e8d-b704c5bdb4de_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-20260630.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_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_019e3bd8-6168-7a65-89d1-ef7310e2232f_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">(Acquisition) 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/2026/elts/us-gaap-2026.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_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_019e3bd8-6168-7b10-98e2-a8eb1555c08e_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Investments Classified by Contractual Maturity Date</link:label>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments Classified by Contractual Maturity Date [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:to="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_019e3bd8-60c7-7f66-a796-3d20d7e546e3_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-20260630.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_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_019e3bd8-60c7-7483-80f0-8298e5e51d91_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/2026/elts/us-gaap-2026.xsd#us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <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/2026/ecd-2026.xsd#ecd_RecoveryOfErrCompDisclosureLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:to="lab_ecd_RecoveryOfErrCompDisclosureLineItems" 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/2026/ecd-2026.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_EquityMethodInvestmentsDisclosureTextBlock_019e3bd8-6167-75a2-9393-f42a789bc617_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/2026/elts/us-gaap-2026.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_ScheduleOfVariableInterestEntitiesTextBlock_019e3bd8-6168-7a8a-8568-2c31776790ea_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/2026/elts/us-gaap-2026.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_TreasuryStockCommonShares_019e3bd8-61f1-755b-85a6-c8be94676d1d_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_019e3bd8-61f1-7418-96e8-ae0fc74994bf_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_019e3bd8-61f1-71ae-9b1a-4277c7a62e37_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/2026/elts/us-gaap-2026.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_us-gaap_PremiumsEarnedNet_019e3bd8-60c7-7ef7-a3fd-4b95d81999db_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_019e3bd8-60c7-7239-809e-518232bd569e_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_019e3bd8-60c7-7011-bf7d-dbb9b3235b3d_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/2026/elts/us-gaap-2026.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_OtherCostAndExpenseOperating_019e3bd8-60c7-77a7-a848-ba00c01d1929_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherCostAndExpenseOperating" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherCostAndExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherCostAndExpenseOperating" xlink:to="lab_us-gaap_OtherCostAndExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities_019e3bd8-6167-7f4d-b9d4-9fe2671fbf78_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustments to reconcile net income to net cash provided by operating activities</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Reconcile Net Income to Cash Provided by (Used in) Operating Activity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:to="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_019e3bd8-6167-7065-991d-96bebf5c88c5_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/2026/elts/us-gaap-2026.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_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_019e3bd8-60c7-7bba-a3ac-94c7dcc6d134_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/2026/elts/us-gaap-2026.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_RelatedPartyMember_019e3bd8-60c8-7ae1-ab6f-889854913b25_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/2026/elts/us-gaap-2026.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_IncomeTaxesPaidNet_019e3bd8-61f1-797e-92e8-aba990c06fdc_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 Tax Paid, after Refund Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxesPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_dei_EntityInteractiveDataCurrent_019e3bd8-6168-713c-abe7-6f3b6091f440_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/2026/dei-2026.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_EffectsOfReinsuranceLineItems_019e3bd8-6168-7c39-96d3-1926461afda1_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/2026/elts/us-gaap-2026.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_VariableRateAxis_019e3bd8-60c7-797f-b23c-6092bb413fd5_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:label id="lab_us-gaap_VariableRateAxis_label_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableRateAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateAxis" xlink:to="lab_us-gaap_VariableRateAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_019e3bd8-60c7-728b-96f2-4bb3688ffeab_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>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" 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 One Through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost"/>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax_019e3bd8-6167-7848-a804-0117640da1bb_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 (losses) gains 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/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax"/>
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    <link:label id="lab_dei_EntitySmallBusiness_019e3bd8-60c8-7621-919d-fde18781f68f_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/2026/dei-2026.xsd#dei_EntitySmallBusiness"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntitySmallBusiness" xlink:to="lab_dei_EntitySmallBusiness" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_019e3bd8-60c7-75c7-b930-635933490999_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/2026/elts/us-gaap-2026.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_UnearnedPremiums_019e3bd8-5ff8-7ff3-8d29-59e1567a3aaf_terseLabel_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_us-gaap_UnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_UnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnearnedPremiums" xlink:to="lab_us-gaap_UnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife_019e3bd8-60c7-780e-be26-8f2a01438957_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">Intangible Asset, Finite-Lived, Acquired, Weighted-Average Amortization Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AcquiredFiniteLivedIntangibleAssetsWeightedAverageUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.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_EffectiveIncomeTaxRateReconciliationTable_019e3bd8-5ff8-7a7d-9d04-d49d3eeaeed0_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/2026/elts/us-gaap-2026.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationTable"/>
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    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedGain_019e3bd8-6167-76c6-a88a-ac6ddf490d05_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/2026/elts/us-gaap-2026.xsd#us-gaap_EquitySecuritiesFvNiRealizedGain"/>
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    <link:label id="lab_ecd_MnpiDiscTimedForCompValFlag_terseLabel_en-US" xlink:label="lab_ecd_MnpiDiscTimedForCompValFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">MNPI Disclosure Timed for Compensation Value</link:label>
    <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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MnpiDiscTimedForCompValFlag" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MnpiDiscTimedForCompValFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MnpiDiscTimedForCompValFlag" xlink:to="lab_ecd_MnpiDiscTimedForCompValFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets_019e3bd8-61f2-7890-9d0e-b0143a0470e9_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying equity</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Underlying Equity in Net Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets"/>
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    <link:label id="lab_skwd_TermLoanFacilityMember_019e3bd8-6167-762b-9f3f-33aafae26a6b_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-20260630.xsd#skwd_TermLoanFacilityMember"/>
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    <link:label id="lab_dei_DocumentType_019e3bd8-60c7-7e2a-bac0-71a62968a65d_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>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentType" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_DocumentType"/>
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    <link:label id="lab_us-gaap_InsuranceCommissions_019e3bd8-6168-754b-9180-8710369f5000_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/2026/elts/us-gaap-2026.xsd#us-gaap_InsuranceCommissions"/>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems"/>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_SignificantAccountingPoliciesTextBlock"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_019e3bd8-60c7-736c-b69a-3797436ac7d6_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_019e3bd8-60c7-7c63-82df-b8aa99da8a64_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_019e3bd8-60c7-79d1-82fe-31f907196339_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_019e3bd8-60c7-76de-bdc6-205e1645b550_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/2026/elts/us-gaap-2026.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_skwd_NotesPayableMember_019e3bd8-60c7-70d7-bbfa-8b57485c3eff_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-20260630.xsd#skwd_NotesPayableMember"/>
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    <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/2026/elts/us-gaap-2026.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_ProceedsFromIssuanceOfLongTermDebt_019e3bd8-6168-7826-99d2-456a3c457f0d_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/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromIssuanceOfLongTermDebt"/>
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    <link:label id="lab_dei_LocalPhoneNumber_019e3bd8-6168-7f5a-9881-b19f9f41d672_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/2026/dei-2026.xsd#dei_LocalPhoneNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_LocalPhoneNumber" xlink:to="lab_dei_LocalPhoneNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_019e3bd8-6168-797f-b31d-ba050580c105_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/2026/elts/us-gaap-2026.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_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e3bd8-6167-7a27-87e0-f42508a1e2c7_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_019e3bd8-6167-7eca-bfd0-0e8685fc2b10_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/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
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    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_019e3bd8-60c8-7844-9f8a-584d7fbccae4_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>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour_019e3bd8-60c7-73fe-b0f5-641e73ef196e_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">Intangible Asset, Finite-Lived, Estimated Amortization Expense, Year Four</link:label>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward_019e3bd8-6167-70be-a3f0-8cd6013d15ff_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">Intangible Asset, Finite-Lived [Roll Forward]</link:label>
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    <link:label id="lab_srt_CounterpartyNameAxis_label_en-US" xlink:label="lab_srt_CounterpartyNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Counterparty Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CounterpartyNameAxis" xlink:href="https://xbrl.fasb.org/srt/2026/elts/srt-2026.xsd#srt_CounterpartyNameAxis"/>
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    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_019e3bd8-60c7-7bbc-b92e-43e3a1e0e347_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/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAndStockholdersEquityAbstract"/>
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    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_019e3bd8-6168-79a1-964a-16024420546f_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/2026/elts/us-gaap-2026.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_ReinsuranceTextBlock_019e3bd8-60c7-70b2-875e-e405e438abfe_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/2026/elts/us-gaap-2026.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_skwd_IntangibleAssetsAcquired_019e3bd8-60c7-7241-a71b-4eef26edb7e2_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-20260630.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_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/2026/ecd-2026.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_LiabilityForClaimsAndClaimsAdjustmentExpenseAfterAcquisition_019e3bd8-6168-712f-8f29-5c54931936da_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-20260630.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_ScheduleOfVariableInterestEntitiesTable_019e3bd8-60c7-7130-bd88-27e7e3ee618f_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/2026/elts/us-gaap-2026.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_SupplementalCashFlowInformationAbstract_019e3bd8-60c7-7b94-a966-a4b6c3fa0dc7_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/2026/elts/us-gaap-2026.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_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_019e3bd8-60c7-78fb-9f44-982e9db0e31e_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_PaymentsForLossesAndLossAdjustmentExpense_019e3bd8-60c7-7fba-ae3b-f6b7c67adbe6_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/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:to="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_019e3bd8-6167-740d-9d9e-7f312d1930c3_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/2026/elts/us-gaap-2026.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_country_BM_019e3bd8-60c7-7c7e-b609-5545d0d91a06_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/2026/country-2026.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_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/2026/ecd-2026.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_dei_EntityTaxIdentificationNumber_019e3bd8-61f1-7dd3-81bf-3f416e4fddfa_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/2026/dei-2026.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_skwd_RestrictedAssetsLloydsFundsHeld_019e3bd8-6168-73d0-a728-dd126dbf362d_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-20260630.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_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssetsAbstract_019e3bd8-6167-73c2-ac79-fe8fd0279101_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/2026/elts/us-gaap-2026.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_PremiumsWrittenGrossAbstract_019e3bd8-61f1-71af-97bf-752e2b8e41ab_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/2026/elts/us-gaap-2026.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_us-gaap_NotesPayable_019e3bd8-6167-7866-b103-9ab3d557cf57_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/2026/elts/us-gaap-2026.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_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock_019e3bd8-6168-79d7-b300-088aefbdeb61_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Identifiable Intangible Assets</link:label>
    <link:label id="lab_us-gaap_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock_label_en-US" xlink:label="lab_us-gaap_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Business Combination, Intangible Asset, Acquired, Finite-Lived and Indefinite-Lived [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock" xlink:to="lab_us-gaap_FiniteLivedAndIndefiniteLivedIntangibleAssetsAcquiredAsPartOfBusinessCombinationTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NonCompetesMember_019e3bd8-60c8-7182-a165-4db9e1b6e6b4_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-20260630.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_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_019e3bd8-6168-701c-9fe9-af41daa47e11_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/2026/elts/us-gaap-2026.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_dei_EntityIncorporationStateCountryCode_019e3bd8-60c7-7916-b54b-52dc3d04916f_terseLabel_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_label_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityIncorporationStateCountryCode" xlink:href="https://xbrl.sec.gov/dei/2026/dei-2026.xsd#dei_EntityIncorporationStateCountryCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityIncorporationStateCountryCode" xlink:to="lab_dei_EntityIncorporationStateCountryCode" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BaseRateMember_019e3bd8-6168-715e-ba7e-62eb492c1bbf_terseLabel_en-US" xlink:label="lab_us-gaap_BaseRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Base Rate</link:label>
    <link:label id="lab_us-gaap_BaseRateMember_label_en-US" xlink:label="lab_us-gaap_BaseRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Base Rate [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BaseRateMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BaseRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BaseRateMember" xlink:to="lab_us-gaap_BaseRateMember" 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/2026/ecd-2026.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_ecd_MtrlTermsOfTrdArrTextBlock_terseLabel_en-US" xlink:label="lab_ecd_MtrlTermsOfTrdArrTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Material Terms of Trading Arrangement</link:label>
    <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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MtrlTermsOfTrdArrTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2026/ecd-2026.xsd#ecd_MtrlTermsOfTrdArrTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MtrlTermsOfTrdArrTextBlock" xlink:to="lab_ecd_MtrlTermsOfTrdArrTextBlock" 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/2026/ecd-2026.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_skwd_TrancheBDDTLMember_019e3bd8-61f1-716f-b641-94b3a420c89d_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-20260630.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_us-gaap_DebtInstrumentAxis_019e3bd8-6168-70e1-921d-06ab737977a4_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/2026/elts/us-gaap-2026.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_skwd_NumberOfUnderwritingDivisions_019e3bd8-61f1-7fb4-a247-c079bdb8ea98_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-20260630.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_019e3bd8-60c7-7da4-a3cf-14c45156c010_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-20260630.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_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities_019e3bd8-60c7-7c39-812f-292d840a974e_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maturities, calls and paydowns of fixed maturity securities held-to-maturity</link:label>
    <link:label id="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Maturities, Prepayments and Calls of Held-to-Maturity Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:to="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfHeldToMaturitySecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_019e3bd8-6168-79d3-b746-300324b32ec3_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic earnings per share (in dollar per share)</link:label>
    <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/2026/elts/us-gaap-2026.xsd#us-gaap_EarningsPerShareBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasic" xlink:to="lab_us-gaap_EarningsPerShareBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_019e3bd8-60c7-72f5-9a4c-c03eb3fd005e_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_skwd_DebtInstrumentFixedRatePeriodDomain_019e3bd8-6167-7c10-846e-9f5355419436_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-20260630.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_PaymentsForProceedsFromLongtermInvestments_019e3bd8-6167-7f3a-a34e-e5dbb81ed446_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/2026/elts/us-gaap-2026.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_skwd_StrategicPartnerSyndicatesMember_019e3bd8-61f1-72ae-b8aa-e674647cb6f0_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-20260630.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_019e3bd8-6167-7127-9c65-002328777efd_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-20260630.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_019e3bd8-6167-7a7b-b1e8-de17d78a6c89_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-20260630.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_019e3bd8-6167-7991-8776-ecfde64aebea_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-20260630.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_DeferredPolicyAcquisitionCostAmortizationExpense_019e3bd8-5ff8-7f96-87c2-96f4593db9c9_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_019e3bd8-6168-79ad-90f1-ff3bad315f43_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-20260630.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_019e3bd8-60c7-73f2-bd03-e77337f3945d_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-20260630.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_us-gaap_FairValueDisclosureItemAmountsDomain_019e3bd8-60c8-742c-8817-728be0540c46_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/2026/elts/us-gaap-2026.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_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/2026/ecd-2026.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_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/2026/dei-2026.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_skwd_SPA1925Member_019e3bd8-61f2-787f-b5c9-397b96587309_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-20260630.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_019e3bd8-61f1-7b2c-b154-8889e7b1b55e_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-20260630.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_PriorPeriodReclassificationAdjustmentDescription_019e3bd8-6168-754d-a399-5df285c43be6_terseLabel_en-US" xlink:label="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reclassifications</link:label>
    <link:label id="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription_label_en-US" xlink:label="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reclassification, Comparability Adjustment [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PriorPeriodReclassificationAdjustmentDescription"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PriorPeriodReclassificationAdjustmentDescription" xlink:to="lab_us-gaap_PriorPeriodReclassificationAdjustmentDescription" 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/2026/elts/us-gaap-2026.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_skwd_EquityMethodInvestmentsUnfundedCommitment_019e3bd8-6168-73ea-ae8d-c51bf87fa6ca_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-20260630.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_country_GB_019e3bd8-60c7-7949-88b0-e3b7e147ce2e_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/2026/country-2026.xsd#country_GB"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_country_GB" xlink:to="lab_country_GB" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_019e3bd8-6168-73bc-a053-d77e0c5147d3_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table]</link:label>
    <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/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" 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/2026/ecd-2026.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_us-gaap_AssumedPremiumsEarned_019e3bd8-6168-7024-84de-6aa631620568_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/2026/elts/us-gaap-2026.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_HedgingRelationshipDomain_019e3bd8-60c7-79e1-84b3-0c52266c1991_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>
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    <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"/>
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    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_019e3bd8-61f1-71a5-a61a-5393c0e18b98_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Numerator</link:label>
    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_label_en-US" xlink:label="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock Dividends and Other Adjustments [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract"/>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions_019e3bd8-61f1-7c15-a26f-5988e250d2a2_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>
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    <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>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions" xlink:href="skwd-20260630.xsd#skwd_DebtSecuritiesAvailableForSaleAllowanceForCreditLossNumberOfPositions"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract"/>
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    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_019e3bd8-6167-7cec-a254-015a4837b37e_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/2026/elts/us-gaap-2026.xsd#us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainLossOnInvestmentsTextBlock"/>
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    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Asset, Recurring Basis, Still Held, Unrealized Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisChangeInUnrealizedGainLoss"/>
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    <link:label id="lab_dei_EntityAddressAddressLine2_019e3bd8-60c7-7783-92bc-ef18d8620435_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/2026/dei-2026.xsd#dei_EntityAddressAddressLine2"/>
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    <link:label id="lab_skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet_019e3bd8-60c8-73a7-9071-df4b98c12377_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>
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    <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-20260630.xsd#skwd_BusinessCombinationRecognizedAssetAcquiredReinsuranceRecoverableNet"/>
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    <link:label id="lab_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock_019e3bd8-6167-7c4c-bae1-38c4a9b1321a_terseLabel_en-US" xlink:label="lab_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Foreign Currency</link:label>
    <link:label id="lab_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Foreign Currency Transactions and Translations Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ForeignCurrencyTransactionsAndTranslationsPolicyTextBlock"/>
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    <link:label id="lab_dei_EntityAddressAddressLine1_019e3bd8-60c7-7b13-a739-989c37156184_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/2026/dei-2026.xsd#dei_EntityAddressAddressLine1"/>
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    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_019e3bd8-5ff8-72aa-a5ce-39fb698832a8_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/2026/elts/us-gaap-2026.xsd#us-gaap_BenefitsLossesAndExpenses"/>
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    <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/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
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    <link:label id="lab_us-gaap_FairValueHedgingMember_019e3bd8-6168-7d1c-b629-6ebdc7ba6432_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/2026/elts/us-gaap-2026.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_PremiumsReceivableAtCarryingValue_019e3bd8-6168-72e2-9755-f6e475f446c9_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/2026/elts/us-gaap-2026.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
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    <link:label id="lab_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember_label_en-US" xlink:label="lab_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Variable Interest Entity, Primary Beneficiary [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityPrimaryBeneficiaryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_VariableInterestEntityPrimaryBeneficiaryMember"/>
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