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<ownershipDocument>

    <schemaVersion>X0202</schemaVersion>

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    <periodOfReport>2006-07-03</periodOfReport>

    <notSubjectToSection16>0</notSubjectToSection16>

    <issuer>
        <issuerCik>0001090403</issuerCik>
        <issuerName>HEALTHEXTRAS INC</issuerName>
        <issuerTradingSymbol>HLEX</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001276621</rptOwnerCik>
            <rptOwnerName>DONOVAN MICHAEL P</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>800 KING FARM BOULEVARD</rptOwnerStreet1>
            <rptOwnerStreet2>4TH FLOOR</rptOwnerStreet2>
            <rptOwnerCity>ROCKVILLE</rptOwnerCity>
            <rptOwnerState>MD</rptOwnerState>
            <rptOwnerZipCode>20850</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
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            <isOfficer>1</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
            <officerTitle>Chief Financial Officer</officerTitle>
        </reportingOwnerRelationship>
    </reportingOwner>

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            <expirationDate>
                <value>2010-06-07</value>
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                <underlyingSecurityTitle>
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            <expirationDate>
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    <footnotes>
        <footnote id="F1">Sale is pursuant to a 10b5-1 plan.</footnote>
        <footnote id="F2">A total of 280,000 options were granted on June 7, 2000 under the HealthExtras, Inc. 1999 Stock Option Plan.  These options vested in four equal annual installments beginning on the first anniversary of the date of grant.</footnote>
        <footnote id="F3">A total of 120,000 options were granted on October 4, 2000 under the HealthExtras, Inc. 2000 Stock Option Plan. These options vested in four equal annual installments beginning on the first anniversary of the date of grant.</footnote>
        <footnote id="F4">A total of 400,000 options were granted on June 10, 2002 under the HealthExtras, Inc. 1999 Stock Option Plan. These options vested in four equal annual installments beginning on the first anniversary of the date of grant; however, all options not yet vested as of December 31, 2005 became vested and exercisable as of that date.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>Thomas M. Farah for Michael P. Donovan by Power of Attorney</signatureName>
        <signatureDate>2006-07-06</signatureDate>
    </ownerSignature>
</ownershipDocument>
