<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2026 Workiva-->
<!--r:019e228f-9c7c-7b25-a67b-10fb5f019784,g:e8deb132-b379-4756-a596-51fcec9ff080-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:arcroleRef arcroleURI="https://xbrl.org/2023/arcrole/summation-item" xlink:type="simple" xlink:href="https://www.xbrl.org/2023/calculation-1.1.xsd#summation-item"/>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/CONSOLIDATEDBALANCESHEETS" xlink:type="simple" xlink:href="mstr-20260630.xsd#CONSOLIDATEDBALANCESHEETS"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/CONSOLIDATEDBALANCESHEETS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_019e228f-9eb1-7fab-a206-6fd3cf63fecb" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Liabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_019e228f-9eb1-739f-b1d8-089461d08bed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e228f-9eb1-7fab-a206-6fd3cf63fecb" xlink:to="loc_us-gaap_LiabilitiesCurrent_019e228f-9eb1-739f-b1d8-089461d08bed" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtNoncurrent_019e228f-9eb1-711b-a5bb-bd2619906e98" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e228f-9eb1-7fab-a206-6fd3cf63fecb" xlink:to="loc_us-gaap_LongTermDebtNoncurrent_019e228f-9eb1-711b-a5bb-bd2619906e98" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerLiabilityNoncurrent_019e228f-9eb1-78ae-9afc-143eb92ce457" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ContractWithCustomerLiabilityNoncurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e228f-9eb1-7fab-a206-6fd3cf63fecb" xlink:to="loc_us-gaap_ContractWithCustomerLiabilityNoncurrent_019e228f-9eb1-78ae-9afc-143eb92ce457" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_019e228f-9eb1-7ea0-b764-00523167e70d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingLeaseLiabilityNoncurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e228f-9eb1-7fab-a206-6fd3cf63fecb" xlink:to="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_019e228f-9eb1-7ea0-b764-00523167e70d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLiabilitiesNoncurrent_019e228f-9eb1-7574-a35a-04ddb9c42290" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherLiabilitiesNoncurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e228f-9eb1-7fab-a206-6fd3cf63fecb" xlink:to="loc_us-gaap_OtherLiabilitiesNoncurrent_019e228f-9eb1-7574-a35a-04ddb9c42290" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxLiabilitiesNet_019e228f-9eb1-7be9-b6d7-c17b71ecea03" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredIncomeTaxLiabilitiesNet"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_019e228f-9eb1-7fab-a206-6fd3cf63fecb" xlink:to="loc_us-gaap_DeferredIncomeTaxLiabilitiesNet_019e228f-9eb1-7be9-b6d7-c17b71ecea03" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_019e228f-9eb1-7944-9adb-eb1321bb66c8" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_AccountsPayableAccruedExpensesAndOperatingLeaseLiabilitiesCurrent_019e228f-9eb1-77d1-978a-8e06fd7c60c0" xlink:href="mstr-20260630.xsd#mstr_AccountsPayableAccruedExpensesAndOperatingLeaseLiabilitiesCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e228f-9eb1-7944-9adb-eb1321bb66c8" xlink:to="loc_mstr_AccountsPayableAccruedExpensesAndOperatingLeaseLiabilitiesCurrent_019e228f-9eb1-77d1-978a-8e06fd7c60c0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeRelatedLiabilitiesCurrent_019e228f-9eb1-72cd-a23c-abc22aa009ef" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EmployeeRelatedLiabilitiesCurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e228f-9eb1-7944-9adb-eb1321bb66c8" xlink:to="loc_us-gaap_EmployeeRelatedLiabilitiesCurrent_019e228f-9eb1-72cd-a23c-abc22aa009ef" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPayableCurrent_019e228f-9eb1-7c3b-8336-e48f9cc51297" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestPayableCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e228f-9eb1-7944-9adb-eb1321bb66c8" xlink:to="loc_us-gaap_InterestPayableCurrent_019e228f-9eb1-7c3b-8336-e48f9cc51297" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DividendsPayableCurrent_019e228f-9eb1-70d9-b557-16aa11821d4c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DividendsPayableCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e228f-9eb1-7944-9adb-eb1321bb66c8" xlink:to="loc_us-gaap_DividendsPayableCurrent_019e228f-9eb1-70d9-b557-16aa11821d4c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtCurrent_019e228f-9eb1-7b74-8c2f-79b26afcf044" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtCurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e228f-9eb1-7944-9adb-eb1321bb66c8" xlink:to="loc_us-gaap_LongTermDebtCurrent_019e228f-9eb1-7b74-8c2f-79b26afcf044" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerLiabilityCurrent_019e228f-9eb1-7594-8367-87a244a136fa" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ContractWithCustomerLiabilityCurrent"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_019e228f-9eb1-7944-9adb-eb1321bb66c8" xlink:to="loc_us-gaap_ContractWithCustomerLiabilityCurrent_019e228f-9eb1-7594-8367-87a244a136fa" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019e228f-9eb1-7b1f-823d-a2df76fdb223" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockValue_019e228f-9eb1-7822-ae52-463951310628" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PreferredStockValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e228f-9eb1-7b1f-823d-a2df76fdb223" xlink:to="loc_us-gaap_PreferredStockValue_019e228f-9eb1-7822-ae52-463951310628" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue_019e228f-9eb1-7895-a23d-a12aac649435" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommonStockValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e228f-9eb1-7b1f-823d-a2df76fdb223" xlink:to="loc_us-gaap_CommonStockValue_019e228f-9eb1-7895-a23d-a12aac649435" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapitalCommonStock_019e228f-9eb1-7c87-8079-a134a718fd4a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AdditionalPaidInCapitalCommonStock"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e228f-9eb1-7b1f-823d-a2df76fdb223" xlink:to="loc_us-gaap_AdditionalPaidInCapitalCommonStock_019e228f-9eb1-7c87-8079-a134a718fd4a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019e228f-9eb1-76f9-b7b3-0ef895414c48" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e228f-9eb1-7b1f-823d-a2df76fdb223" xlink:to="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_019e228f-9eb1-76f9-b7b3-0ef895414c48" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019e228f-9eb1-788e-b6f5-2cd57d1b682e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_019e228f-9eb1-7b1f-823d-a2df76fdb223" xlink:to="loc_us-gaap_RetainedEarningsAccumulatedDeficit_019e228f-9eb1-788e-b6f5-2cd57d1b682e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets_019e228f-9eb1-77f3-a212-841d62c40f39" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Assets"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_019e228f-9eb1-7e84-a07b-257c4f632f82" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e228f-9eb1-77f3-a212-841d62c40f39" xlink:to="loc_us-gaap_AssetsCurrent_019e228f-9eb1-7e84-a07b-257c4f632f82" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CryptoAssetFairValue_019e228f-9eb1-732a-8806-75e051983246" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CryptoAssetFairValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e228f-9eb1-77f3-a212-841d62c40f39" xlink:to="loc_us-gaap_CryptoAssetFairValue_019e228f-9eb1-732a-8806-75e051983246" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet_019e228f-9eb1-7126-8d94-99add5109abf" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e228f-9eb1-77f3-a212-841d62c40f39" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentNet_019e228f-9eb1-7126-8d94-99add5109abf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseRightOfUseAsset_019e228f-9eb1-77aa-98a5-49effcdcfc8b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingLeaseRightOfUseAsset"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e228f-9eb1-77f3-a212-841d62c40f39" xlink:to="loc_us-gaap_OperatingLeaseRightOfUseAsset_019e228f-9eb1-77aa-98a5-49effcdcfc8b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_DepositsAndOtherAssets_019e228f-9eb1-7c08-a799-e7507dae8fe1" xlink:href="mstr-20260630.xsd#mstr_DepositsAndOtherAssets"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e228f-9eb1-77f3-a212-841d62c40f39" xlink:to="loc_mstr_DepositsAndOtherAssets_019e228f-9eb1-7c08-a799-e7507dae8fe1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxAssetsNet_019e228f-9eb1-7bb2-b15a-dbe577620f29" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredIncomeTaxAssetsNet"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_019e228f-9eb1-77f3-a212-841d62c40f39" xlink:to="loc_us-gaap_DeferredIncomeTaxAssetsNet_019e228f-9eb1-7bb2-b15a-dbe577620f29" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_019e228f-9eb1-71b7-8cad-4e92d804b6c2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AssetsCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019e228f-9eb1-784d-9739-2ca40008486c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_019e228f-9eb1-71b7-8cad-4e92d804b6c2" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_019e228f-9eb1-784d-9739-2ca40008486c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalentsAtCarryingValue_019e228f-9eb1-79b2-aa72-8d54ca620bac" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RestrictedCashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_019e228f-9eb1-71b7-8cad-4e92d804b6c2" xlink:to="loc_us-gaap_RestrictedCashAndCashEquivalentsAtCarryingValue_019e228f-9eb1-79b2-aa72-8d54ca620bac" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent_019e228f-9eb1-77de-87c8-68e91e584e46" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_019e228f-9eb1-71b7-8cad-4e92d804b6c2" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtSecuritiesCurrent_019e228f-9eb1-77de-87c8-68e91e584e46" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsReceivableNetCurrent_019e228f-9eb1-7758-86da-66525a0a6f37" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsReceivableNetCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_019e228f-9eb1-71b7-8cad-4e92d804b6c2" xlink:to="loc_us-gaap_AccountsReceivableNetCurrent_019e228f-9eb1-7758-86da-66525a0a6f37" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidExpenseAndOtherAssetsCurrent_019faa4b-53e8-729a-ba3e-0afef9f3982f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PrepaidExpenseAndOtherAssetsCurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_019e228f-9eb1-71b7-8cad-4e92d804b6c2" xlink:to="loc_us-gaap_PrepaidExpenseAndOtherAssetsCurrent_019faa4b-53e8-729a-ba3e-0afef9f3982f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity_019e228f-9eb1-7fe3-a5f1-4662f98ffe2d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_019e228f-9eb1-7fe4-9d56-bd3cddbce3d6" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_Liabilities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019e228f-9eb1-7fe3-a5f1-4662f98ffe2d" xlink:to="loc_us-gaap_Liabilities_019e228f-9eb1-7fe4-9d56-bd3cddbce3d6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingencies_019e228f-9eb1-7998-ae6d-115de3402cf0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CommitmentsAndContingencies"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019e228f-9eb1-7fe3-a5f1-4662f98ffe2d" xlink:to="loc_us-gaap_CommitmentsAndContingencies_019e228f-9eb1-7998-ae6d-115de3402cf0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_019e228f-9eb1-7555-8672-4170a30c0945" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_StockholdersEquity"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019e228f-9eb1-7fe3-a5f1-4662f98ffe2d" xlink:to="loc_us-gaap_StockholdersEquity_019e228f-9eb1-7555-8672-4170a30c0945" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_019e228f-9eb1-711f-8785-30078994d6fb" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_TemporaryEquityCarryingAmountAttributableToParent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_019e228f-9eb1-7fe3-a5f1-4662f98ffe2d" xlink:to="loc_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_019e228f-9eb1-711f-8785-30078994d6fb" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/CONSOLIDATEDSTATEMENTSOFOPERATIONS" xlink:type="simple" xlink:href="mstr-20260630.xsd#CONSOLIDATEDSTATEMENTSOFOPERATIONS"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/CONSOLIDATEDSTATEMENTSOFOPERATIONS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_019e228f-9eb1-7be1-8abe-c74998b21d16" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossProfit_019e228f-9eb1-7576-9608-d1b410574dee" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GrossProfit"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_019e228f-9eb1-7be1-8abe-c74998b21d16" xlink:to="loc_us-gaap_GrossProfit_019e228f-9eb1-7576-9608-d1b410574dee" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_019e228f-9eb1-7b04-aa2c-0fa2ac20bcb8" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingExpenses"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_019e228f-9eb1-7be1-8abe-c74998b21d16" xlink:to="loc_us-gaap_OperatingExpenses_019e228f-9eb1-7b04-aa2c-0fa2ac20bcb8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossProfit_019e228f-9eb1-7206-9915-0d54dce02181" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GrossProfit"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_019e228f-9eb1-7a03-ab71-6c798d96e80b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_GrossProfit_019e228f-9eb1-7206-9915-0d54dce02181" xlink:to="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_019e228f-9eb1-7a03-ab71-6c798d96e80b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfGoodsAndServicesSold_019e228f-9eb1-7ddd-a391-78f5fa0ea69d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CostOfGoodsAndServicesSold"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_GrossProfit_019e228f-9eb1-7206-9915-0d54dce02181" xlink:to="loc_us-gaap_CostOfGoodsAndServicesSold_019e228f-9eb1-7ddd-a391-78f5fa0ea69d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e228f-9eb1-7c0f-bc15-2610bddd4ec4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019e228f-9eb1-7c5f-841d-cb1d3a89ea96" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e228f-9eb1-7c0f-bc15-2610bddd4ec4" xlink:to="loc_us-gaap_NetIncomeLoss_019e228f-9eb1-7c5f-841d-cb1d3a89ea96" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockDividendsIncomeStatementImpact_019e228f-9eb1-7537-9bde-7ae4b061282c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PreferredStockDividendsIncomeStatementImpact"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019e228f-9eb1-7c0f-bc15-2610bddd4ec4" xlink:to="loc_us-gaap_PreferredStockDividendsIncomeStatementImpact_019e228f-9eb1-7537-9bde-7ae4b061282c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019e228f-9eb1-7eb9-8f26-bcf3d08f91b0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e228f-9eb1-7f37-971c-354c5027ef32" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9eb1-7eb9-8f26-bcf3d08f91b0" xlink:to="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e228f-9eb1-7f37-971c-354c5027ef32" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_019e228f-9eb1-7500-ba5e-eb99856ad220" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9eb1-7eb9-8f26-bcf3d08f91b0" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_019e228f-9eb1-7500-ba5e-eb99856ad220" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_019e228f-9eb1-7476-868d-856855c7e75f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingExpenses"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpense_019e228f-9eb1-77db-b477-f4f3478cada7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SellingAndMarketingExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019e228f-9eb1-7476-868d-856855c7e75f" xlink:to="loc_us-gaap_SellingAndMarketingExpense_019e228f-9eb1-77db-b477-f4f3478cada7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResearchAndDevelopmentExpense_019e228f-9eb1-7fb0-a0a9-3efab1dea692" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ResearchAndDevelopmentExpense"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019e228f-9eb1-7476-868d-856855c7e75f" xlink:to="loc_us-gaap_ResearchAndDevelopmentExpense_019e228f-9eb1-7fb0-a0a9-3efab1dea692" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense_019e228f-9eb1-74d9-a8a3-78f9bc141642" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019e228f-9eb1-7476-868d-856855c7e75f" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpense_019e228f-9eb1-74d9-a8a3-78f9bc141642" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CryptoAssetUnrealizedGainLossOperating_019e228f-9eb1-71d5-9b80-b7171a107988" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CryptoAssetUnrealizedGainLossOperating"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_019e228f-9eb1-7476-868d-856855c7e75f" xlink:to="loc_us-gaap_CryptoAssetUnrealizedGainLossOperating_019e228f-9eb1-71d5-9b80-b7171a107988" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e228f-9eb1-7c4f-a238-838839545f4e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_019e228f-9eb1-7da5-8a53-fda998a2fa09" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e228f-9eb1-7c4f-a238-838839545f4e" xlink:to="loc_us-gaap_OperatingIncomeLoss_019e228f-9eb1-7da5-8a53-fda998a2fa09" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestIncomeExpenseNonoperatingNet_019e228f-9eb1-71d9-9fe3-c2cb994dbdc3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestIncomeExpenseNonoperatingNet"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e228f-9eb1-7c4f-a238-838839545f4e" xlink:to="loc_us-gaap_InterestIncomeExpenseNonoperatingNet_019e228f-9eb1-71d9-9fe3-c2cb994dbdc3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019e228f-9eb1-7e05-a492-e9a9d7e6574c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainsLossesOnExtinguishmentOfDebt"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e228f-9eb1-7c4f-a238-838839545f4e" xlink:to="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019e228f-9eb1-7e05-a492-e9a9d7e6574c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherNonoperatingIncomeExpense_019f9708-6052-75d2-a843-536a69ee3e98" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherNonoperatingIncomeExpense"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_019e228f-9eb1-7c4f-a238-838839545f4e" xlink:to="loc_us-gaap_OtherNonoperatingIncomeExpense_019f9708-6052-75d2-a843-536a69ee3e98" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/CONSOLIDATEDSTATEMENTSOFCOMPREHENSIVELOSSINCOME" xlink:type="simple" xlink:href="mstr-20260630.xsd#CONSOLIDATEDSTATEMENTSOFCOMPREHENSIVELOSSINCOME"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/CONSOLIDATEDSTATEMENTSOFCOMPREHENSIVELOSSINCOME" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019e228f-9eb1-7bf3-94b7-4dab07711123" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent_019f970e-7e49-71f9-aa09-432bd6b45446" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019e228f-9eb1-7bf3-94b7-4dab07711123" xlink:to="loc_us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent_019f970e-7e49-71f9-aa09-432bd6b45446" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeForeignCurrencyTransactionAndTranslationAdjustmentNetOfTaxPortionAttributableToParent_019e228f-9eb1-72f0-b6d5-2affa7be5bdc" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeForeignCurrencyTransactionAndTranslationAdjustmentNetOfTaxPortionAttributableToParent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019e228f-9eb1-7bf3-94b7-4dab07711123" xlink:to="loc_us-gaap_OtherComprehensiveIncomeForeignCurrencyTransactionAndTranslationAdjustmentNetOfTaxPortionAttributableToParent_019e228f-9eb1-72f0-b6d5-2affa7be5bdc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax_019e228f-9eb1-7ff5-94bd-3fda33d8101d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019e228f-9eb1-7a8f-8372-98f1bd7e481a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_019e228f-9eb1-7ff5-94bd-3fda33d8101d" xlink:to="loc_us-gaap_NetIncomeLoss_019e228f-9eb1-7a8f-8372-98f1bd7e481a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019e228f-9eb1-79b3-b3eb-e7ab79ba58fc" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_019e228f-9eb1-7ff5-94bd-3fda33d8101d" xlink:to="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_019e228f-9eb1-79b3-b3eb-e7ab79ba58fc" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/CONSOLIDATEDSTATEMENTSOFCASHFLOWS" xlink:type="simple" xlink:href="mstr-20260630.xsd#CONSOLIDATEDSTATEMENTSOFCASHFLOWS"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/CONSOLIDATEDSTATEMENTSOFCASHFLOWS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e228f-9eb1-7fd7-896c-a376664fd857" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-77dd-96ea-af3e23067dd9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e228f-9eb1-7fd7-896c-a376664fd857" xlink:to="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-77dd-96ea-af3e23067dd9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e228f-9eb1-7f1a-ada7-59d727a7b3d1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e228f-9eb1-7fd7-896c-a376664fd857" xlink:to="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e228f-9eb1-7f1a-ada7-59d727a7b3d1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-7a9f-baef-55af6de60356" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e228f-9eb1-7fd7-896c-a376664fd857" xlink:to="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-7a9f-baef-55af6de60356" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsIncludingDisposalGroupAndDiscontinuedOperations_019e228f-9eb1-78e7-b996-75ba2983e1fb" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsIncludingDisposalGroupAndDiscontinuedOperations"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_019e228f-9eb1-7fd7-896c-a376664fd857" xlink:to="loc_us-gaap_EffectOfExchangeRateOnCashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsIncludingDisposalGroupAndDiscontinuedOperations_019e228f-9eb1-78e7-b996-75ba2983e1fb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e228f-9eb1-7a93-937b-f4f375ca4614" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentForAcquisitionCryptoAsset_019e228f-9eb1-729b-a75f-6b5e79b40b11" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentForAcquisitionCryptoAsset"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e228f-9eb1-7a93-937b-f4f375ca4614" xlink:to="loc_us-gaap_PaymentForAcquisitionCryptoAsset_019e228f-9eb1-729b-a75f-6b5e79b40b11" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromDisposalCryptoAsset_019e228f-9eb1-75fd-bd7b-3cb64b9488b4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromDisposalCryptoAsset"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e228f-9eb1-7a93-937b-f4f375ca4614" xlink:to="loc_us-gaap_ProceedsFromDisposalCryptoAsset_019e228f-9eb1-75fd-bd7b-3cb64b9488b4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_AdvanceDepositsOnPurchasesOfPropertyAndEquipment_019e228f-9eb1-7997-9fc7-ef9207288b1b" xlink:href="mstr-20260630.xsd#mstr_AdvanceDepositsOnPurchasesOfPropertyAndEquipment"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e228f-9eb1-7a93-937b-f4f375ca4614" xlink:to="loc_mstr_AdvanceDepositsOnPurchasesOfPropertyAndEquipment_019e228f-9eb1-7997-9fc7-ef9207288b1b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_019f971f-697f-7381-b2f6-15aa4ba80e4b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e228f-9eb1-7a93-937b-f4f375ca4614" xlink:to="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_019f971f-697f-7381-b2f6-15aa4ba80e4b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireShortTermInvestments_019f971f-697f-7ef9-a594-8aaff9d7a207" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsToAcquireShortTermInvestments"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e228f-9eb1-7a93-937b-f4f375ca4614" xlink:to="loc_us-gaap_PaymentsToAcquireShortTermInvestments_019f971f-697f-7ef9-a594-8aaff9d7a207" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfShortTermInvestments_019f971f-697f-7cae-916b-af4bed7ae50b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromSaleOfShortTermInvestments"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_019e228f-9eb1-7a93-937b-f4f375ca4614" xlink:to="loc_us-gaap_ProceedsFromSaleOfShortTermInvestments_019f971f-697f-7cae-916b-af4bed7ae50b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfCommonStock_019e228f-9eb1-7abe-9611-7bc7ffb17e11" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromIssuanceOfCommonStock"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_ProceedsFromIssuanceOfCommonStock_019e228f-9eb1-7abe-9611-7bc7ffb17e11" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsOfStockIssuanceCosts_019e228f-9eb1-76ed-88f3-357ba2320909" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsOfStockIssuanceCosts"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_PaymentsOfStockIssuanceCosts_019e228f-9eb1-76ed-88f3-357ba2320909" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock_019e228f-9eb1-7bbb-a2c3-03dd22ab1993" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock_019e228f-9eb1-7bbb-a2c3-03dd22ab1993" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsOfDividendsPreferredStockAndPreferenceStock_019e228f-9eb1-7b15-b74b-16194a21a6bd" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsOfDividendsPreferredStockAndPreferenceStock"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_PaymentsOfDividendsPreferredStockAndPreferenceStock_019e228f-9eb1-7b15-b74b-16194a21a6bd" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockOptionsExercised_019e228f-9eb1-7493-a2aa-8a4e5f5f8892" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromStockOptionsExercised"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_ProceedsFromStockOptionsExercised_019e228f-9eb1-7493-a2aa-8a4e5f5f8892" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockPlans_019e228f-9eb1-735a-b09f-d349e1227a93" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromStockPlans"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_ProceedsFromStockPlans_019e228f-9eb1-735a-b09f-d349e1227a93" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfConvertibleDebt_019e228f-9eb1-72b9-b03d-aba98a1af4be" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RepaymentsOfConvertibleDebt"/>
    <link:calculationArc order="7" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_RepaymentsOfConvertibleDebt_019e228f-9eb1-72b9-b03d-aba98a1af4be" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities_019e228f-9eb1-72f5-a95d-f629e4ad5142" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromPaymentsForOtherFinancingActivities"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_ProceedsFromPaymentsForOtherFinancingActivities_019e228f-9eb1-72f5-a95d-f629e4ad5142" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromConvertibleDebt_019e228f-9eb1-7782-b3cf-0e2f0529228b" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromConvertibleDebt"/>
    <link:calculationArc order="9" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_ProceedsFromConvertibleDebt_019e228f-9eb1-7782-b3cf-0e2f0529228b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsOfDebtIssuanceCosts_019e228f-9eb1-7943-9735-53de6196bd8c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_PaymentsOfDebtIssuanceCosts"/>
    <link:calculationArc order="10" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_PaymentsOfDebtIssuanceCosts_019e228f-9eb1-7943-9735-53de6196bd8c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_PaymentsToSettleConversionsAndRedemptionOfConvertibleDebt_019f972c-11df-7c96-8259-9e164fafd8be" xlink:href="mstr-20260630.xsd#mstr_PaymentsToSettleConversionsAndRedemptionOfConvertibleDebt"/>
    <link:calculationArc order="11" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_mstr_PaymentsToSettleConversionsAndRedemptionOfConvertibleDebt_019f972c-11df-7c96-8259-9e164fafd8be" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfSecuredDebt_019f972c-11df-7a63-a5be-632cdc4677d2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ProceedsFromIssuanceOfSecuredDebt"/>
    <link:calculationArc order="12" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_ProceedsFromIssuanceOfSecuredDebt_019f972c-11df-7a63-a5be-632cdc4677d2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfOtherLongTermDebt_019faa57-fc7f-77c6-8420-0f8ee35997a1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RepaymentsOfOtherLongTermDebt"/>
    <link:calculationArc order="13" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_019e228f-9eb1-757e-a9e4-0d86ab6a5071" xlink:to="loc_us-gaap_RepaymentsOfOtherLongTermDebt_019faa57-fc7f-77c6-8420-0f8ee35997a1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019e228f-9eb1-79ee-9625-4c13fd2712e2" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_NetIncomeLoss_019e228f-9eb1-79ee-9625-4c13fd2712e2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationDepletionAndAmortization_019e228f-9eb1-7308-9e51-f8f095ba6493" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DepreciationDepletionAndAmortization"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_DepreciationDepletionAndAmortization_019e228f-9eb1-7308-9e51-f8f095ba6493" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseRightOfUseAssetAmortizationExpense_019e228f-9eb1-7452-95ab-675901cc8c0f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OperatingLeaseRightOfUseAssetAmortizationExpense"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_OperatingLeaseRightOfUseAssetAmortizationExpense_019e228f-9eb1-7452-95ab-675901cc8c0f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxesAndTaxCredits_019e228f-9eb1-7b3c-a3af-3a8b3f1cb9e0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredIncomeTaxesAndTaxCredits"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_DeferredIncomeTaxesAndTaxCredits_019e228f-9eb1-7b3c-a3af-3a8b3f1cb9e0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation_019e228f-9eb1-7114-bc8d-b975e1da9302" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensation"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_ShareBasedCompensation_019e228f-9eb1-7114-bc8d-b975e1da9302" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CryptoAssetUnrealizedGainLossOperating_019e228f-9eb1-7291-be85-02eade10b17f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CryptoAssetUnrealizedGainLossOperating"/>
    <link:calculationArc order="6" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_CryptoAssetUnrealizedGainLossOperating_019e228f-9eb1-7291-be85-02eade10b17f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfFinancingCosts_019e228f-9eb1-73ab-b20b-90cd37adde94" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AmortizationOfFinancingCosts"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_AmortizationOfFinancingCosts_019e228f-9eb1-73ab-b20b-90cd37adde94" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019e228f-9eb1-7935-8979-27320adbc4a0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainsLossesOnExtinguishmentOfDebt"/>
    <link:calculationArc order="8" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019e228f-9eb1-7935-8979-27320adbc4a0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherNoncashIncomeExpense_019e228f-9eb1-7b21-b39c-3d548a58146f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_OtherNoncashIncomeExpense"/>
    <link:calculationArc order="9" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_OtherNoncashIncomeExpense_019e228f-9eb1-7b21-b39c-3d548a58146f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsReceivable_019e228f-9eb1-7019-a328-681e05c223f4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInAccountsReceivable"/>
    <link:calculationArc order="10" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsReceivable_019e228f-9eb1-7019-a328-681e05c223f4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets_019e228f-9eb1-7b40-99dd-6e2199c6e72c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets"/>
    <link:calculationArc order="11" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets_019e228f-9eb1-7b40-99dd-6e2199c6e72c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDepositOtherAssets_019e228f-9eb1-75cb-9ece-b7a9cd3c695c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInDepositOtherAssets"/>
    <link:calculationArc order="12" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_IncreaseDecreaseInDepositOtherAssets_019e228f-9eb1-75cb-9ece-b7a9cd3c695c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_019e228f-9eb1-7828-bec8-4b75e54352b3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities"/>
    <link:calculationArc order="13" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_019e228f-9eb1-7828-bec8-4b75e54352b3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInEmployeeRelatedLiabilities_019e228f-9eb1-7447-b071-85c0494e892c" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInEmployeeRelatedLiabilities"/>
    <link:calculationArc order="14" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_IncreaseDecreaseInEmployeeRelatedLiabilities_019e228f-9eb1-7447-b071-85c0494e892c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInInterestPayableNet_019e228f-9eb1-7f74-abe8-fb7b29c731d0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInInterestPayableNet"/>
    <link:calculationArc order="15" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_IncreaseDecreaseInInterestPayableNet_019e228f-9eb1-7f74-abe8-fb7b29c731d0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInContractWithCustomerLiability_019e228f-9eb1-7688-8110-2432f327625d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncreaseDecreaseInContractWithCustomerLiability"/>
    <link:calculationArc order="16" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_us-gaap_IncreaseDecreaseInContractWithCustomerLiability_019e228f-9eb1-7688-8110-2432f327625d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_IncreaseDecreaseInOperatingLeaseLiabilitiesAndOtherLongTermLiabilities_019f971c-f3a1-7b1c-b75c-cc6a4b0cfc2e" xlink:href="mstr-20260630.xsd#mstr_IncreaseDecreaseInOperatingLeaseLiabilitiesAndOtherLongTermLiabilities"/>
    <link:calculationArc order="17" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_019e228f-9eb1-762e-9085-58f41e5735b7" xlink:to="loc_mstr_IncreaseDecreaseInOperatingLeaseLiabilitiesAndOtherLongTermLiabilities_019f971c-f3a1-7b1c-b75c-cc6a4b0cfc2e" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/SummaryofSignificantAccountingPoliciesInterestIncomeExpenseDetails" xlink:type="simple" xlink:href="mstr-20260630.xsd#SummaryofSignificantAccountingPoliciesInterestIncomeExpenseDetails"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/SummaryofSignificantAccountingPoliciesInterestIncomeExpenseDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestIncomeExpenseNonoperatingNet_019fbb16-9b35-75fb-8921-0efe246fed35" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestIncomeExpenseNonoperatingNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeInterest_019fbb16-9b35-7a30-b012-7b2197e12ca7" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InvestmentIncomeInterest"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_InterestIncomeExpenseNonoperatingNet_019fbb16-9b35-75fb-8921-0efe246fed35" xlink:to="loc_us-gaap_InvestmentIncomeInterest_019fbb16-9b35-7a30-b012-7b2197e12ca7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseNonoperating_019fbb16-9b35-703a-b6a3-feea791e52c9" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestExpenseNonoperating"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_InterestIncomeExpenseNonoperatingNet_019fbb16-9b35-75fb-8921-0efe246fed35" xlink:to="loc_us-gaap_InterestExpenseNonoperating_019fbb16-9b35-703a-b6a3-feea791e52c9" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/ContractBalancesAccountsReceivableDetails" xlink:type="simple" xlink:href="mstr-20260630.xsd#ContractBalancesAccountsReceivableDetails"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/ContractBalancesAccountsReceivableDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsReceivableNetCurrent_019e228f-9eb1-7331-9f0d-94fa56a3b7af" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AccountsReceivableNetCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BilledContractReceivables_019e228f-9eb1-70e1-bc92-c34bd778890d" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_BilledContractReceivables"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccountsReceivableNetCurrent_019e228f-9eb1-7331-9f0d-94fa56a3b7af" xlink:to="loc_us-gaap_BilledContractReceivables_019e228f-9eb1-70e1-bc92-c34bd778890d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllowanceForDoubtfulAccountsReceivableCurrent_019e228f-9eb1-77f0-82a5-59c75a5749ab" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AllowanceForDoubtfulAccountsReceivableCurrent"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_AccountsReceivableNetCurrent_019e228f-9eb1-7331-9f0d-94fa56a3b7af" xlink:to="loc_us-gaap_AllowanceForDoubtfulAccountsReceivableCurrent_019e228f-9eb1-77f0-82a5-59c75a5749ab" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/LongtermDebtOutstandingDebtDetails" xlink:type="simple" xlink:href="mstr-20260630.xsd#LongtermDebtOutstandingDebtDetails"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/LongtermDebtOutstandingDebtDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt_019e228f-9eb1-70fe-b5fc-aa91d8fbc21a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebt"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtCurrent_019e228f-9eb1-7a60-9331-8b949ead37c4" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_019e228f-9eb1-70fe-b5fc-aa91d8fbc21a" xlink:to="loc_us-gaap_LongTermDebtCurrent_019e228f-9eb1-7a60-9331-8b949ead37c4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtNoncurrent_019e228f-9eb1-786b-b771-72929a42b813" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_019e228f-9eb1-70fe-b5fc-aa91d8fbc21a" xlink:to="loc_us-gaap_LongTermDebtNoncurrent_019e228f-9eb1-786b-b771-72929a42b813" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/LongtermDebtConvertibleDebtInstrumentsDetails" xlink:type="simple" xlink:href="mstr-20260630.xsd#LongtermDebtConvertibleDebtInstrumentsDetails"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/LongtermDebtConvertibleDebtInstrumentsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt_019e228f-9eb1-7f7c-9e47-c4790b92db3f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebt"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount_019e228f-9eb1-7cdd-b5fe-74bd5eed9230" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_019e228f-9eb1-7f7c-9e47-c4790b92db3f" xlink:to="loc_us-gaap_DebtInstrumentCarryingAmount_019e228f-9eb1-7cdd-b5fe-74bd5eed9230" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredFinanceCostsNet_019e228f-9eb1-7d4d-a71e-f4dbe4d73eed" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_DeferredFinanceCostsNet"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_019e228f-9eb1-7f7c-9e47-c4790b92db3f" xlink:to="loc_us-gaap_DeferredFinanceCostsNet_019e228f-9eb1-7d4d-a71e-f4dbe4d73eed" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/LongtermDebtInterestExpenseDetails" xlink:type="simple" xlink:href="mstr-20260630.xsd#LongtermDebtInterestExpenseDetails"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/LongtermDebtInterestExpenseDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseNonoperating_019e228f-9eb1-754f-8ee8-0dce69e5dda1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestExpenseNonoperating"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseDebt_019e228f-9eb1-7d7e-910b-2912084f7131" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestExpenseDebt"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_InterestExpenseNonoperating_019e228f-9eb1-754f-8ee8-0dce69e5dda1" xlink:to="loc_us-gaap_InterestExpenseDebt_019e228f-9eb1-7d7e-910b-2912084f7131" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfFinancingCosts_019e228f-9eb1-7f6a-b199-8690fed72b76" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AmortizationOfFinancingCosts"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_InterestExpenseNonoperating_019e228f-9eb1-754f-8ee8-0dce69e5dda1" xlink:to="loc_us-gaap_AmortizationOfFinancingCosts_019e228f-9eb1-7f6a-b199-8690fed72b76" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/LongtermDebtMaturitiesofDebtInstrumentsDetails" xlink:type="simple" xlink:href="mstr-20260630.xsd#LongtermDebtMaturitiesofDebtInstrumentsDetails"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/LongtermDebtMaturitiesofDebtInstrumentsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_mstr_LongTermDebtMaturitiesRepaymentsDue_019e228f-9eb1-753b-a9eb-ee4557525a18" xlink:href="mstr-20260630.xsd#mstr_LongTermDebtMaturitiesRepaymentsDue"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths_019e228f-9eb1-730d-9766-60baefb612ec" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_mstr_LongTermDebtMaturitiesRepaymentsDue_019e228f-9eb1-753b-a9eb-ee4557525a18" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths_019e228f-9eb1-730d-9766-60baefb612ec" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo_019e228f-9eb1-7976-a719-849469f47f4f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_mstr_LongTermDebtMaturitiesRepaymentsDue_019e228f-9eb1-753b-a9eb-ee4557525a18" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo_019e228f-9eb1-7976-a719-849469f47f4f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree_019e228f-9eb1-7f09-9578-5d561bec543f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_mstr_LongTermDebtMaturitiesRepaymentsDue_019e228f-9eb1-753b-a9eb-ee4557525a18" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree_019e228f-9eb1-7f09-9578-5d561bec543f" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/SharebasedCompensationStockOptionActivityDetails" xlink:type="simple" xlink:href="mstr-20260630.xsd#SharebasedCompensationStockOptionActivityDetails"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/SharebasedCompensationStockOptionActivityDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue_019e228f-9eb2-7ecf-8d50-825c0de90368" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsExercisableIntrinsicValue1_019e228f-9eb2-7072-9899-fd7dd18e8cff" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsExercisableIntrinsicValue1"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue_019e228f-9eb2-7ecf-8d50-825c0de90368" xlink:to="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsExercisableIntrinsicValue1_019e228f-9eb2-7072-9899-fd7dd18e8cff" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue_019e228f-9eb2-736d-a6fb-0cb155930879" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingIntrinsicValue_019e228f-9eb2-7ecf-8d50-825c0de90368" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue_019e228f-9eb2-736d-a6fb-0cb155930879" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/BasicandDilutedEarningsLossperCommonShareComputationofBasicandDilutedLossperShareDetails" xlink:type="simple" xlink:href="mstr-20260630.xsd#BasicandDilutedEarningsLossperCommonShareComputationofBasicandDilutedLossperShareDetails"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/BasicandDilutedEarningsLossperCommonShareComputationofBasicandDilutedLossperShareDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019e228f-9f6c-7ab8-bbd7-63bcd5fa08f6" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_019f974e-0d2b-7cdc-82fa-1430da539fe0" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019e228f-9f6c-7ab8-bbd7-63bcd5fa08f6" xlink:to="loc_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_019f974e-0d2b-7cdc-82fa-1430da539fe0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock_019f974e-0d2b-70ad-9035-ed59caac799e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019e228f-9f6c-7ab8-bbd7-63bcd5fa08f6" xlink:to="loc_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock_019f974e-0d2b-70ad-9035-ed59caac799e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToConversionOfDebtSecurities_019f974e-0d2b-7118-9880-fc2e821d8eea" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncrementalCommonSharesAttributableToConversionOfDebtSecurities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019e228f-9f6c-7ab8-bbd7-63bcd5fa08f6" xlink:to="loc_us-gaap_IncrementalCommonSharesAttributableToConversionOfDebtSecurities_019f974e-0d2b-7118-9880-fc2e821d8eea" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_019e228f-9f6c-7cd5-8d87-ec881cfae2ac" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_019e228f-9f6c-7ab8-bbd7-63bcd5fa08f6" xlink:to="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_019e228f-9f6c-7cd5-8d87-ec881cfae2ac" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_019f974b-1bd6-767e-9e44-874e5dee99bf" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019f974b-1bd6-793c-8e55-9b8998af92cd" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_019f974b-1bd6-767e-9e44-874e5dee99bf" xlink:to="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_019f974b-1bd6-793c-8e55-9b8998af92cd" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestOnConvertibleDebtNetOfTax_019f974b-1bd6-7a73-bafb-c67505707c25" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestOnConvertibleDebtNetOfTax"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_019f974b-1bd6-767e-9e44-874e5dee99bf" xlink:to="loc_us-gaap_InterestOnConvertibleDebtNetOfTax_019f974b-1bd6-7a73-bafb-c67505707c25" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConvertiblePreferredDividendsNetOfTax_019f974b-1bd6-7e11-adc5-79dd66fe14ef" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_ConvertiblePreferredDividendsNetOfTax"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_019f974b-1bd6-767e-9e44-874e5dee99bf" xlink:to="loc_us-gaap_ConvertiblePreferredDividendsNetOfTax_019f974b-1bd6-7e11-adc5-79dd66fe14ef" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.strategysoftware.com/role/SegmentInformationScheduleofRevenueandExpensesDetails" xlink:type="simple" xlink:href="mstr-20260630.xsd#SegmentInformationScheduleofRevenueandExpensesDetails"/>
  <link:calculationLink xlink:role="http://www.strategysoftware.com/role/SegmentInformationScheduleofRevenueandExpensesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_019e228f-9f6c-70c0-a7ea-053dbb6d8a49" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_019e228f-9f6c-70c0-a7ea-053dbb6d8a49" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_SellingAndMarketingExpenseAdjusted_019e228f-9f6c-7245-9cdd-39bb70a6410f" xlink:href="mstr-20260630.xsd#mstr_SellingAndMarketingExpenseAdjusted"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_mstr_SellingAndMarketingExpenseAdjusted_019e228f-9f6c-7245-9cdd-39bb70a6410f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_MaintenanceExpense_019e228f-9f6c-7a54-95ca-61bf5638e4e8" xlink:href="mstr-20260630.xsd#mstr_MaintenanceExpense"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_mstr_MaintenanceExpense_019e228f-9f6c-7a54-95ca-61bf5638e4e8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_ConsultingExpense_019e228f-9f6c-72cc-b27b-be66bc2288bb" xlink:href="mstr-20260630.xsd#mstr_ConsultingExpense"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_mstr_ConsultingExpense_019e228f-9f6c-72cc-b27b-be66bc2288bb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_CloudExpense_019e228f-9f6c-75e5-be8e-2dcd87fac1eb" xlink:href="mstr-20260630.xsd#mstr_CloudExpense"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_mstr_CloudExpense_019e228f-9f6c-75e5-be8e-2dcd87fac1eb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_TechnologyExpense_019e228f-9f6c-799f-82f0-2c899400cfbf" xlink:href="mstr-20260630.xsd#mstr_TechnologyExpense"/>
    <link:calculationArc order="6" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_mstr_TechnologyExpense_019e228f-9f6c-799f-82f0-2c899400cfbf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_CorporateResourcesExpense_019e228f-9f6c-75b9-b4dc-6ad66508f901" xlink:href="mstr-20260630.xsd#mstr_CorporateResourcesExpense"/>
    <link:calculationArc order="7" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_mstr_CorporateResourcesExpense_019e228f-9f6c-75b9-b4dc-6ad66508f901" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CryptoAssetUnrealizedGainLossOperating_019e228f-9f6c-79ff-ade9-4b92038b8db3" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CryptoAssetUnrealizedGainLossOperating"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_us-gaap_CryptoAssetUnrealizedGainLossOperating_019e228f-9f6c-79ff-ade9-4b92038b8db3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CustodyFees_019e228f-9f6c-7b0f-a6eb-96a461d2256f" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_CustodyFees"/>
    <link:calculationArc order="9" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_us-gaap_CustodyFees_019e228f-9f6c-7b0f-a6eb-96a461d2256f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllocatedShareBasedCompensationExpense_019e228f-9f6c-7902-93a9-cc7025d40f41" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_AllocatedShareBasedCompensationExpense"/>
    <link:calculationArc order="10" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_us-gaap_AllocatedShareBasedCompensationExpense_019e228f-9f6c-7902-93a9-cc7025d40f41" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_mstr_PayrollTaxesOnEquityAwardExercisesAndVesting_019e228f-9f6c-7696-92d7-83f8cea4a86b" xlink:href="mstr-20260630.xsd#mstr_PayrollTaxesOnEquityAwardExercisesAndVesting"/>
    <link:calculationArc order="11" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_mstr_PayrollTaxesOnEquityAwardExercisesAndVesting_019e228f-9f6c-7696-92d7-83f8cea4a86b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingOtherItemAmount_019e228f-9f6c-7144-9187-e4cf8c63746a" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_SegmentReportingOtherItemAmount"/>
    <link:calculationArc order="12" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_us-gaap_SegmentReportingOtherItemAmount_019e228f-9f6c-7144-9187-e4cf8c63746a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestIncomeExpenseNonoperatingNet_019e228f-9f6c-7827-8374-5ef2f89b0271" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_InterestIncomeExpenseNonoperatingNet"/>
    <link:calculationArc order="13" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_us-gaap_InterestIncomeExpenseNonoperatingNet_019e228f-9f6c-7827-8374-5ef2f89b0271" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_019e228f-9f6c-71d2-819b-e87585ecb52e" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:calculationArc order="14" weight="-1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_019e228f-9f6c-71d2-819b-e87585ecb52e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019faab8-bf81-7d91-952d-c4fc4bc9ddf1" xlink:href="https://xbrl.fasb.org/us-gaap/2026/elts/us-gaap-2026.xsd#us-gaap_GainsLossesOnExtinguishmentOfDebt"/>
    <link:calculationArc order="15" weight="1.0" xlink:arcrole="https://xbrl.org/2023/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_019e228f-9f6c-7bba-a715-a4cd7e400a6e" xlink:to="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_019faab8-bf81-7d91-952d-c4fc4bc9ddf1" xlink:type="arc"/>
  </link:calculationLink>
</link:linkbase>
