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<!--Generated by DFIN XBRL Instance Document - http://www.dfinsolutions.com/ - Version R3.0 - on 12-April-2024 [09:07:02] {AM}-->
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<annotation>
<appinfo>
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<link:linkbaseRef xlink:type="simple" xlink:href="mstr-20231231_def.xml" xlink:role="http://www.xbrl.org/2003/role/definitionLinkbaseRef" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" />
<link:linkbaseRef xlink:type="simple" xlink:href="mstr-20231231_lab.xml" xlink:role="http://www.xbrl.org/2003/role/labelLinkbaseRef" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" />
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<import namespace="http://www.xbrl.org/2003/instance" schemaLocation="http://www.xbrl.org/2003/xbrl-instance-2003-12-31.xsd" />
<import namespace="http://www.xbrl.org/2003/linkbase" schemaLocation="http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd" />
<import namespace="http://xbrl.sec.gov/dei/2023" schemaLocation="https://xbrl.sec.gov/dei/2023/dei-2023.xsd" />
<import namespace="http://xbrl.sec.gov/dei-sub/2023" schemaLocation="https://xbrl.sec.gov/dei/2023/dei-sub-2023.xsd" />
<import namespace="http://www.xbrl.org/dtr/type/2020-01-21" schemaLocation="https://www.xbrl.org/dtr/type/2020-01-21/types.xsd" />
<import namespace="http://fasb.org/srt/2023" schemaLocation="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd" />
<import namespace="http://fasb.org/srt-types/2023" schemaLocation="https://xbrl.fasb.org/srt/2023/elts/srt-types-2023.xsd" />
<import namespace="http://xbrl.sec.gov/ecd-sub/2023" schemaLocation="https://xbrl.sec.gov/ecd/2023/ecd-sub-2023.xsd" />
<import namespace="http://xbrl.sec.gov/ecd/2023" schemaLocation="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd" />
<import namespace="http://www.xbrl.org/2006/ref" schemaLocation="http://www.xbrl.org/2006/ref-2006-02-27.xsd" />
<import namespace="http://xbrl.org/2005/xbrldt" schemaLocation="http://www.xbrl.org/2005/xbrldt-2005.xsd" />
<import namespace="http://fasb.org/srt-roles/2023" schemaLocation="https://xbrl.fasb.org/srt/2023/elts/srt-roles-2023.xsd" />
<element name="AggregateValueForStockAwardsAndOptionAwardsIncludedInSctAmountsForTheCoveredFiscalyearMember" type="dtr-types:domainItemType" abstract="true" xbrli:periodType="duration" nillable="true" id="mstr_AggregateValueForStockAwardsAndOptionAwardsIncludedInSctAmountsForTheCoveredFiscalyearMember" substitutionGroup="xbrli:item" />
<element name="ChangeAsOfTheVestingDateFromTheEndOfThePriorFiscalYearInFairValueOfAwardsGrantedInAnyPriorFiscalYearForWhichVestingConditionsWereSatisfiedDuringTheCoveredFiscalYearMember" type="dtr-types:domainItemType" abstract="true" xbrli:periodType="duration" nillable="true" id="mstr_ChangeAsOfTheVestingDateFromTheEndOfThePriorFiscalYearInFairValueOfAwardsGrantedInAnyPriorFiscalYearForWhichVestingConditionsWereSatisfiedDuringTheCoveredFiscalYearMember" substitutionGroup="xbrli:item" />
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<element name="FairValueAtYearEndOfAwardsGrantedDuringTheCoveredFiscalYearThatWereOutstandingAndUnvestedAtTheCoveredFiscalYearEndMember" type="dtr-types:domainItemType" abstract="true" xbrli:periodType="duration" nillable="true" id="mstr_FairValueAtYearEndOfAwardsGrantedDuringTheCoveredFiscalYearThatWereOutstandingAndUnvestedAtTheCoveredFiscalYearEndMember" substitutionGroup="xbrli:item" />
<element name="YearOverYearChangeInFairValueAtCoveredFiscalYearEndOfAwardsGrantedInAnyPriorFiscalYearThatWereOutstandingAndUnvestedAtTheCoveredFiscalYearEndMember" type="dtr-types:domainItemType" abstract="true" xbrli:periodType="duration" nillable="true" id="mstr_YearOverYearChangeInFairValueAtCoveredFiscalYearEndOfAwardsGrantedInAnyPriorFiscalYearThatWereOutstandingAndUnvestedAtTheCoveredFiscalYearEndMember" substitutionGroup="xbrli:item" />
<element name="Mr.LeMember" type="dtr-types:domainItemType" abstract="true" xbrli:periodType="duration" nillable="true" id="mstr_Mr.LeMember" substitutionGroup="xbrli:item" />
<element name="Mr.SaylorMember" type="dtr-types:domainItemType" abstract="true" xbrli:periodType="duration" nillable="true" id="mstr_Mr.SaylorMember" substitutionGroup="xbrli:item" />
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