<SEC-DOCUMENT>0001127602-23-023290.txt : 20230828
<SEC-HEADER>0001127602-23-023290.hdr.sgml : 20230828
<ACCEPTANCE-DATETIME>20230828163444
ACCESSION NUMBER:		0001127602-23-023290
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20230824
FILED AS OF DATE:		20230828
DATE AS OF CHANGE:		20230828

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			LEVINE DOUGLAS
		CENTRAL INDEX KEY:			0001164694

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-15204
		FILM NUMBER:		231216367

	MAIL ADDRESS:	
		STREET 1:		2602 NW 5TH AVENUE
		CITY:			MIAMI
		STATE:			FL
		ZIP:			33127

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			KINGSWAY FINANCIAL SERVICES INC
		CENTRAL INDEX KEY:			0001072627
		STANDARD INDUSTRIAL CLASSIFICATION:	FIRE, MARINE & CASUALTY INSURANCE [6331]
		IRS NUMBER:				999999999
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	BUSINESS ADDRESS:	
		STREET 1:		10 S. RIVERSIDE PLAZA
		STREET 2:		SUITE 1520
		CITY:			CHICAGO
		STATE:			IL
		ZIP:			60606
		BUSINESS PHONE:		(312) 766-2144

	MAIL ADDRESS:	
		STREET 1:		10 S. RIVERSIDE PLAZA
		STREET 2:		SUITE 1520
		CITY:			CHICAGO
		STATE:			IL
		ZIP:			60606
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>form4.xml
<DESCRIPTION>PRIMARY DOCUMENT
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0508</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2023-08-24</periodOfReport>

    <issuer>
        <issuerCik>0001072627</issuerCik>
        <issuerName>KINGSWAY FINANCIAL SERVICES INC</issuerName>
        <issuerTradingSymbol>KFS</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001164694</rptOwnerCik>
            <rptOwnerName>LEVINE DOUGLAS</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>2602 NW 5TH AVENUE</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>MIAMI</rptOwnerCity>
            <rptOwnerState>FL</rptOwnerState>
            <rptOwnerZipCode>33127</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
        </reportingOwnerRelationship>
    </reportingOwner>

    <aff10b5One>0</aff10b5One>

    <derivativeTable>
        <derivativeTransaction>
            <securityTitle>
                <value>Series B Warrant</value>
                <footnoteId id="F1"/>
            </securityTitle>
            <conversionOrExercisePrice>
                <value>5.00</value>
            </conversionOrExercisePrice>
            <transactionDate>
                <value>2023-08-24</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>D</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionTimeliness></transactionTimeliness>
            <transactionAmounts>
                <transactionShares>
                    <value>241187</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>4.00</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <exerciseDate>
                <value>2016-09-16</value>
            </exerciseDate>
            <expirationDate>
                <value>2023-09-15</value>
            </expirationDate>
            <underlyingSecurity>
                <underlyingSecurityTitle>
                    <value>Common Stock</value>
                </underlyingSecurityTitle>
                <underlyingSecurityShares>
                    <value>241187</value>
                </underlyingSecurityShares>
            </underlyingSecurity>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>0</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </derivativeTransaction>
    </derivativeTable>

    <footnotes>
        <footnote id="F1">The warrants that were sold were not previously reported by the reporting person.  The reporting person has represented to the company that he has held these warrants for greater than six months from the date of the transaction.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>/s/ Debra Rouse, attorney-in-fact for Douglas Levine</signatureName>
        <signatureDate>2023-08-28</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
