<?xml version="1.0" encoding="utf-8"?>
<Return xmlns="http://www.irs.gov/efile" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" returnVersion="2022v5.0">
  <ReturnHeader binaryAttachmentCnt="0">
    <ReturnTs>2023-11-15T10:26:58+00:00</ReturnTs>
    <TaxPeriodEndDt>2022-12-31</TaxPeriodEndDt>
    <ReturnTypeCd>990EZ</ReturnTypeCd>
    <TaxPeriodBeginDt>2022-01-01</TaxPeriodBeginDt>
    <Filer>
      <EIN>061559155</EIN>
      <BusinessName>
        <BusinessNameLine1Txt>Health Benefits Holdings Inc</BusinessNameLine1Txt>
      </BusinessName>
      <BusinessNameControlTxt>HEAL</BusinessNameControlTxt>
      <PhoneNum>2034325530</PhoneNum>
      <USAddress>
        <AddressLine1Txt>C/O Yale U Tax Dept PO Box 208239</AddressLine1Txt>
        <CityNm>New Haven</CityNm>
        <StateAbbreviationCd>CT</StateAbbreviationCd>
        <ZIPCd>065208239</ZIPCd>
      </USAddress>
    </Filer>
    <BusinessOfficerGrp>
      <PersonNm>Stephen C Murphy</PersonNm>
      <PersonTitleTxt>Secretary &amp; Director</PersonTitleTxt>
      <SignatureDt>2023-11-15</SignatureDt>
    </BusinessOfficerGrp>
    <SigningOfficerGrp>
      <PersonFullName>
        <PersonFirstNm>Stephen</PersonFirstNm>
        <PersonLastNm>C Murphy</PersonLastNm>
      </PersonFullName>
      <SSN>999009999</SSN>
    </SigningOfficerGrp>
    <TaxYr>2022</TaxYr>
    <BuildTS>2023-04-26 12:10:37Z</BuildTS>
  </ReturnHeader>
  <ReturnData documentCnt="2">
    <IRS990EZ documentId="IRS990EZ" softwareId="22016089" softwareVersionNum="2022v5.0">
      <MethodOfAccountingAccrualInd>X</MethodOfAccountingAccrualInd>
      <ScheduleBNotRequiredInd>X</ScheduleBNotRequiredInd>
      <WebsiteAddressTxt>N/A</WebsiteAddressTxt>
      <Organization501cInd organization501cTypeTxt="2">X</Organization501cInd>
      <TypeOfOrganizationCorpInd>X</TypeOfOrganizationCorpInd>
      <GrossReceiptsAmt>0</GrossReceiptsAmt>
      <ContributionsGiftsGrantsEtcAmt>0</ContributionsGiftsGrantsEtcAmt>
      <ProgramServiceRevenueAmt>0</ProgramServiceRevenueAmt>
      <MembershipDuesAmt>0</MembershipDuesAmt>
      <InvestmentIncomeAmt>0</InvestmentIncomeAmt>
      <SaleOfAssetsGrossAmt>0</SaleOfAssetsGrossAmt>
      <CostOrOtherBasisExpenseSaleAmt>0</CostOrOtherBasisExpenseSaleAmt>
      <GainOrLossFromSaleOfAssetsAmt>0</GainOrLossFromSaleOfAssetsAmt>
      <SpecialEventsNetIncomeLossAmt>0</SpecialEventsNetIncomeLossAmt>
      <GrossProfitLossSlsOfInvntryAmt>0</GrossProfitLossSlsOfInvntryAmt>
      <OtherRevenueTotalAmt>0</OtherRevenueTotalAmt>
      <TotalRevenueAmt>0</TotalRevenueAmt>
      <GrantsAndSimilarAmountsPaidAmt>0</GrantsAndSimilarAmountsPaidAmt>
      <OtherExpensesTotalAmt>0</OtherExpensesTotalAmt>
      <TotalExpensesAmt>0</TotalExpensesAmt>
      <ExcessOrDeficitForYearAmt>0</ExcessOrDeficitForYearAmt>
      <NetAssetsOrFundBalancesBOYAmt>0</NetAssetsOrFundBalancesBOYAmt>
      <OtherChangesInNetAssetsAmt>0</OtherChangesInNetAssetsAmt>
      <NetAssetsOrFundBalancesEOYAmt>0</NetAssetsOrFundBalancesEOYAmt>
      <CashSavingsAndInvestmentsGrp>
        <BOYAmt>0</BOYAmt>
        <EOYAmt>0</EOYAmt>
      </CashSavingsAndInvestmentsGrp>
      <LandAndBuildingsGrp>
        <BOYAmt>0</BOYAmt>
        <EOYAmt>0</EOYAmt>
      </LandAndBuildingsGrp>
      <OtherAssetsTotalDetail>
        <BOYAmt>0</BOYAmt>
        <EOYAmt>0</EOYAmt>
      </OtherAssetsTotalDetail>
      <Form990TotalAssetsGrp>
        <BOYAmt>0</BOYAmt>
        <EOYAmt>0</EOYAmt>
      </Form990TotalAssetsGrp>
      <SumOfTotalLiabilitiesGrp>
        <BOYAmt>0</BOYAmt>
        <EOYAmt>0</EOYAmt>
      </SumOfTotalLiabilitiesGrp>
      <NetAssetsOrFundBalancesGrp>
        <BOYAmt>0</BOYAmt>
        <EOYAmt>0</EOYAmt>
      </NetAssetsOrFundBalancesGrp>
      <InfoInScheduleOPartIIIInd>X</InfoInScheduleOPartIIIInd>
      <PrimaryExemptPurposeTxt>Hold title to property, collect the income therefrom and turn over the entire amount thereof, less expenses, to Yale University Retiree Health Benefits Coverage Trust, a qualified trust exempt under IRC Section 501(c)(3).</PrimaryExemptPurposeTxt>
      <ProgramSrvcAccomplishmentGrp>
        <DescriptionProgramSrvcAccomTxt>NONE</DescriptionProgramSrvcAccomTxt>
        <GrantsAndAllocationsAmt>0</GrantsAndAllocationsAmt>
        <ProgramServiceExpensesAmt>0</ProgramServiceExpensesAmt>
      </ProgramSrvcAccomplishmentGrp>
      <TotalProgramServiceExpensesAmt>0</TotalProgramServiceExpensesAmt>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>Stephen C Murphy</PersonNm>
        <TitleTxt>Secretary &amp; Director</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.200</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>Alexander C Banker</PersonNm>
        <TitleTxt>VP &amp; Treasurer &amp; Director</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.200</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <OfficerDirectorTrusteeEmplGrp>
        <PersonNm>Matthew ST Mendelsohn</PersonNm>
        <TitleTxt>President &amp; Director</TitleTxt>
        <AverageHrsPerWkDevotedToPosRt>0.200</AverageHrsPerWkDevotedToPosRt>
        <CompensationAmt>0</CompensationAmt>
        <EmployeeBenefitProgramAmt>0</EmployeeBenefitProgramAmt>
        <ExpenseAccountOtherAllwncAmt>0</ExpenseAccountOtherAllwncAmt>
      </OfficerDirectorTrusteeEmplGrp>
      <ActivitiesNotPreviouslyRptInd>false</ActivitiesNotPreviouslyRptInd>
      <ChgMadeToOrgnzngDocNotRptInd>false</ChgMadeToOrgnzngDocNotRptInd>
      <OrganizationHadUBIInd>false</OrganizationHadUBIInd>
      <SubjectToProxyTaxInd>false</SubjectToProxyTaxInd>
      <OrganizationDissolvedEtcInd>false</OrganizationDissolvedEtcInd>
      <DirectIndirectPltclExpendAmt>0</DirectIndirectPltclExpendAmt>
      <Form1120PolFiledInd>false</Form1120PolFiledInd>
      <MadeLoansToFromOfficersInd>false</MadeLoansToFromOfficersInd>
      <ProhibitedTaxShelterTransInd>false</ProhibitedTaxShelterTransInd>
      <BooksInCareOfDetail>
        <BusinessName>
          <BusinessNameLine1Txt>Yale University Tax Department</BusinessNameLine1Txt>
        </BusinessName>
        <USAddress>
          <AddressLine1Txt>PO BOX 208239</AddressLine1Txt>
          <CityNm>New Haven</CityNm>
          <StateAbbreviationCd>CT</StateAbbreviationCd>
          <ZIPCd>065208239</ZIPCd>
        </USAddress>
        <PhoneNum>2034325530</PhoneNum>
      </BooksInCareOfDetail>
      <ForeignFinancialAccountInd>false</ForeignFinancialAccountInd>
      <ForeignOfficeInd>false</ForeignOfficeInd>
      <DonorAdvisedFndsInd>false</DonorAdvisedFndsInd>
      <OperateHospitalInd>false</OperateHospitalInd>
      <TanningServicesProvidedInd>false</TanningServicesProvidedInd>
      <RelatedOrganizationCtrlEntInd>false</RelatedOrganizationCtrlEntInd>
      <TransactionWithControlEntInd>false</TransactionWithControlEntInd>
      <PoliticalCampaignActyInd>false</PoliticalCampaignActyInd>
    </IRS990EZ>
    <IRS990ScheduleO documentId="IRS990ScheduleO" softwareId="22016089" softwareVersionNum="2022v5.0">
      <SupplementalInformationDetail>
        <FormAndLineReferenceDesc>Form 990-EZ, Part III, Exempt Purpose PRIMARY EXEMPT PURPOSE</FormAndLineReferenceDesc>
        <ExplanationTxt>Hold title to property, collect the income therefrom and turn over the entire amount thereof, less expenses, to Yale University Retiree Health Benefits Coverage Trust, a qualified trust exempt under IRC Section 501(c)(3).</ExplanationTxt>
      </SupplementalInformationDetail>
    </IRS990ScheduleO>
  </ReturnData>
</Return>
