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Proc-Type: 2001,MIC-CLEAR
Originator-Name: webmaster@www.sec.gov
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MIC-Info: RSA-MD5,RSA,
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 6EI0xFJUthBCR9WyOLHoCg==

<SEC-DOCUMENT>0001181431-08-039552.txt : 20080618
<SEC-HEADER>0001181431-08-039552.hdr.sgml : 20080618
<ACCEPTANCE-DATETIME>20080618164213
ACCESSION NUMBER:		0001181431-08-039552
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20080616
FILED AS OF DATE:		20080618
DATE AS OF CHANGE:		20080618

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			HEALTHEXTRAS INC
		CENTRAL INDEX KEY:			0001090403
		STANDARD INDUSTRIAL CLASSIFICATION:	INSURANCE AGENTS BROKERS & SERVICES [6411]
		IRS NUMBER:				522181356
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	BUSINESS ADDRESS:	
		STREET 1:		800 KING FARM BOULEVARD
		CITY:			ROCKVILLE
		STATE:			MD
		ZIP:			20850
		BUSINESS PHONE:		3015482900

	MAIL ADDRESS:	
		STREET 1:		800 KING FARM BOULEVARD
		CITY:			ROCKVILLE
		STATE:			MD
		ZIP:			20850

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			BLAIR THOMAS L
		CENTRAL INDEX KEY:			0001018356

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	000-31014
		FILM NUMBER:		08906097

	BUSINESS ADDRESS:	
		STREET 1:		UNITED PAYORS & PROVIDERS INC
		STREET 2:		2275 RESEARCH BLVD
		CITY:			ROCKVILLE
		STATE:			MD
		ZIP:			20850
		BUSINESS PHONE:		3015481000

	MAIL ADDRESS:	
		STREET 1:		UNITED PAYORS & PROVIDERS INC
		STREET 2:		2273 RESEARCH BLVD 2ND FL.
		CITY:			ROCKVILLE
		STATE:			MD
		ZIP:			20850
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>rrd211264.xml
<DESCRIPTION>06/17/08-FSN5 - 10B5-1 PLAN
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0202</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2008-06-16</periodOfReport>

    <notSubjectToSection16>0</notSubjectToSection16>

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

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001018356</rptOwnerCik>
            <rptOwnerName>BLAIR THOMAS L</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>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>237500</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>By Highland Investments II, LLC</value>
                    <footnoteId id="F1"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>150000</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>I</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value>By FedMed, Inc.</value>
                    <footnoteId id="F2"/>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
    </nonDerivativeTable>

    <footnotes>
        <footnote id="F1">Mr. Blair is a member and controlling person of Highland Investments II, LLC.</footnote>
        <footnote id="F2">Mr. Blair is the controlling owner of FedMed, Inc.</footnote>
    </footnotes>

    <remarks>Form 5 of 5 being filed.</remarks>

    <ownerSignature>
        <signatureName>Thomas M. Farah for Thomas L. Blair by Power of Attorney</signatureName>
        <signatureDate>2008-06-18</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
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