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    <filerInfo>
      <liveTestFlag>LIVE</liveTestFlag>
      <filer>
        <issuerCredentials>
          <cik>0000929630</cik>
          <ccc>XXXXXXXX</ccc>
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      </filer>
      <flags>
        <overrideInternetFlag>false</overrideInternetFlag>
        <confirmingCopyFlag>false</confirmingCopyFlag>
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      <investmentCompanyType>N-6</investmentCompanyType>
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          <classId>C000008044</classId>
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        <classInfo>
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        <classInfo>
          <classId>C000008047</classId>
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        <classInfo>
          <classId>C000008048</classId>
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        <classInfo>
          <classId>C000008049</classId>
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    <generalInfo reportEndingPeriod="2021-12-31" isReportPeriodLt12="N"/>
    <registrantInfo>
      <registrantFullName>Separate Account Five of Talcott Resolution Life &amp; Annuity Insurance Co</registrantFullName>
      <investmentCompFileNo>811-08770</investmentCompFileNo>
      <registrantCik>0000929630</registrantCik>
      <registrantLei>549300087C140DT6NN74</registrantLei>
      <registrantstreet1>One Griffin Road North</registrantstreet1>
      <registrantstreet2>Suite S4</registrantstreet2>
      <registrantcity>Windsor</registrantcity>
      <registrantzipCode>06095-1512</registrantzipCode>
      <registrantstate>US-CT</registrantstate>
      <registrantcountry>US</registrantcountry>
      <registrantphoneNumber>9738024193</registrantphoneNumber>
      <websites>
        <website webpage="www.policyowner-services.com"/>
      </websites>
      <locationBooksRecords>
        <locationBooksRecord>
          <officeName>Jackie Walding</officeName>
          <officeAddress1>751 Broad Street</officeAddress1>
          <officeCity>Newark</officeCity>
          <officeStateCountry officeState="US-NJ" officeCountry="US"/>
          <officeRecordsZipCode>07102</officeRecordsZipCode>
          <officePhone>9043131872</officePhone>
          <booksRecordsDesc>Records covering shareholder accounts and portfolio transactions</booksRecordsDesc>
        </locationBooksRecord>
      </locationBooksRecords>
      <isRegistrantFirstFiling>N</isRegistrantFirstFiling>
      <isRegistrantLastFiling>N</isRegistrantLastFiling>
      <registrantFamilyInvComp isRegistrantFamilyInvComp="Y" familyInvCompFullName="Talcott"/>
      <registrantClassificationType>N-6</registrantClassificationType>
      <isSecuritiesActRegistration>Y</isSecuritiesActRegistration>
      <chiefComplianceOfficers>
        <chiefComplianceOfficer>
          <ccoName>Christopher Scott Conner</ccoName>
          <crdNumber>002239639</crdNumber>
          <ccoStreet1>1 Griffin Rd North</ccoStreet1>
          <ccoCity>Windsor</ccoCity>
          <ccoStateCountry ccoState="US-CT" ccoCountry="US"/>
          <ccoZipCode>06095</ccoZipCode>
          <ccoPhone>XXXXXX</ccoPhone>
          <isCcoChangedSinceLastFiling>N</isCcoChangedSinceLastFiling>
          <ccoEmployers>
            <ccoEmployer ccoEmployerName="N/A" ccoEmployerId="N/A"/>
          </ccoEmployers>
        </chiefComplianceOfficer>
      </chiefComplianceOfficers>
      <isRegistrantSubmittedMatter>N</isRegistrantSubmittedMatter>
      <isPreviousLegalProceeding>N</isPreviousLegalProceeding>
      <isPreviousProceedingTerminated>N</isPreviousProceedingTerminated>
      <isFinancialSupportDuringPeriod>N</isFinancialSupportDuringPeriod>
      <isExemptionFromAct>N</isExemptionFromAct>
      <principalUnderwriters>
        <principalUnderwriter>
          <principalUnderwriterName>Pruco Securities, LLC</principalUnderwriterName>
          <principalUnderwriterFileNumber>8-16402</principalUnderwriterFileNumber>
          <principalUnderwriterCrdNumber>000005685</principalUnderwriterCrdNumber>
          <principalUnderwriterLei>N/A</principalUnderwriterLei>
          <principalUnderWriterStateCountry principalUnderWriterState="US-NJ" principalUnderWriterCountry="US"/>
          <isPrincipalUnderwriterAffiliatedWithRegistrant>Y</isPrincipalUnderwriterAffiliatedWithRegistrant>
        </principalUnderwriter>
      </principalUnderwriters>
      <isUnderwriterHiredOrTerminated>N</isUnderwriterHiredOrTerminated>
      <publicAccountants>
        <publicAccountant>
          <publicAccountantName>Deloitte &amp; Touche LLP</publicAccountantName>
          <pcaobNumber>00034</pcaobNumber>
          <publicAccountantLei>N/A</publicAccountantLei>
          <publicAccountantStateCountry publicAccountantState="US-CT" publicAccountantCountry="US"/>
        </publicAccountant>
      </publicAccountants>
      <isPublicAccountantChanged>N</isPublicAccountantChanged>
      <isOpinionOffered>N</isOpinionOffered>
      <isMaterialChange>N</isMaterialChange>
      <isAccountingPrincipleChange>N</isAccountingPrincipleChange>
    </registrantInfo>
    <unitInvestmentTrust>
      <depositors>
        <depositor>
          <depositorName>Talcott Resolution Life and Annuity Insurance Company</depositorName>
          <depositorCrdNo>N/A</depositorCrdNo>
          <depositorLei>3WR91SPXQZD5X605SQ32</depositorLei>
          <depositorStateCountry depositorState="US-CT" depositorCountry="US"/>
          <depositorUltimateParentname>Talcott Resolution Life, Inc.</depositorUltimateParentname>
        </depositor>
      </depositors>
      <uitAdmins>
        <uitAdmin>
          <uitAdminName>Prudential Insurance Company of America</uitAdminName>
          <uitAdminLei>X574KRZ6V5A7UBU45C31</uitAdminLei>
          <uitAdminStateCountry uitAdminState="US-NJ" uitAdminCountry="US"/>
          <isUitAdminAffiliated>N</isUitAdminAffiliated>
          <isUitAdminSubAdmin>N</isUitAdminSubAdmin>
        </uitAdmin>
        <uitAdmin>
          <uitAdminName>DXC Technology Company</uitAdminName>
          <uitAdminLei>549300DOVZ3EDJB7O259</uitAdminLei>
          <uitAdminStateCountry uitAdminState="US-NV" uitAdminCountry="US"/>
          <isUitAdminAffiliated>N</isUitAdminAffiliated>
          <isUitAdminSubAdmin>Y</isUitAdminSubAdmin>
        </uitAdmin>
      </uitAdmins>
      <isUitAdminHiredTerminated>N</isUitAdminHiredTerminated>
      <registrantSeparateInsuranceAccount isRegistrantSeparateInsuranceAccount="Y" separateAccountSeriesId="S000002940"/>
      <numOfContracts>1979</numOfContracts>
      <contractSecurities>
        <contractSecurity separateAccountSecurityName="Director Life (Series II)" separateAccountContractId="C000008044" separateAccountTotalAsset="142529974.307869000000" numContractsSold="0" grossPremiumReceived="37819.170000000000" grossPremiumReceivedSection1035="0.000000000000" numContractsAffected="0" contractValueRedeemed="16974562.921450600000" contractValueRedeemedSection1035="410524.280000000000" numContractsAffectedRedeemed="4"/>
        <contractSecurity separateAccountSecurityName="Director Life (Series I)" separateAccountContractId="C000008045" separateAccountTotalAsset="111820921.271230000000" numContractsSold="0" grossPremiumReceived="91877.980000000000" grossPremiumReceivedSection1035="0.000000000000" numContractsAffected="0" contractValueRedeemed="19703639.310066300000" contractValueRedeemedSection1035="335446.940000000000" numContractsAffectedRedeemed="2"/>
        <contractSecurity separateAccountSecurityName="Putnam Hartford Inheritance Manager Variable Life" separateAccountContractId="C000008046" separateAccountTotalAsset="9353688.747667620000" numContractsSold="0" grossPremiumReceived="0.000000000000" grossPremiumReceivedSection1035="0.000000000000" numContractsAffected="0" contractValueRedeemed="952824.223762898000" contractValueRedeemedSection1035="0.000000000000" numContractsAffectedRedeemed="0"/>
        <contractSecurity separateAccountSecurityName="Putnam Capital Manager Variable Life" separateAccountContractId="C000008047" separateAccountTotalAsset="47991744.147500900000" numContractsSold="0" grossPremiumReceived="29459.210000000000" grossPremiumReceivedSection1035="0.000000000000" numContractsAffected="0" contractValueRedeemed="5191219.560346890000" contractValueRedeemedSection1035="168826.740000000000" numContractsAffectedRedeemed="1"/>
        <contractSecurity separateAccountSecurityName="Select Dimensions Life II" separateAccountContractId="C000008048" separateAccountTotalAsset="1618747.904974450000" numContractsSold="0" grossPremiumReceived="0.000000000000" grossPremiumReceivedSection1035="0.000000000000" numContractsAffected="0" contractValueRedeemed="143169.199625653000" contractValueRedeemedSection1035="0.000000000000" numContractsAffectedRedeemed="0"/>
        <contractSecurity separateAccountSecurityName="Select Dimensions Life" separateAccountContractId="C000008049" separateAccountTotalAsset="5788678.730757730000" numContractsSold="0" grossPremiumReceived="0.000000000000" grossPremiumReceivedSection1035="0.000000000000" numContractsAffected="0" contractValueRedeemed="153818.004747619000" contractValueRedeemedSection1035="0.000000000000" numContractsAffectedRedeemed="0"/>
      </contractSecurities>
      <isRule6C7Reliance>N</isRule6C7Reliance>
      <isRule11A2Reliance>N</isRule11A2Reliance>
      <isRule12D1Dash4Reliance>N</isRule12D1Dash4Reliance>
      <isRule12D1GReliance>N</isRule12D1GReliance>
    </unitInvestmentTrust>
    <signature registrantSignedName="Separate Account Five of Talcott Resolution Life &amp; Annuity Insurance Co" signedDate="2022-03-10" signature="Greg Steffe" title="VP Project Management"/>
  </formData>
</edgarSubmission>
