Kingsway announces public debt offering



    /NOT FOR DISTRIBUTION TO U.S. NEWS WIRE SERVICES OR FOR DISSEMINATION IN
    THE U.S./

    TORONTO, June 21 /CNW/ - (TSX:KFS, NYSE:  KFS) Kingsway Financial Services
Inc. ("Kingsway" or the "Company") today announced that its newly formed
wholly-owned subsidiary Kingsway 2007 General Partnership has filed a
preliminary short form prospectus with the securities regulatory authorities
in each of the provinces and territories of Canada for a proposed public
offering of senior unsecured debentures which will be jointly and severally
guaranteed by Kingsway and Kingsway America Inc. ("Kingsway America"). The
guarantee of Kingsway will be an unsecured senior obligation of Kingsway, will
rank equally with all Kingsway's other unsecured senior indebtedness and will
rank senior to all existing and future subordinated indebtedness of Kingsway.
The guarantee of Kingsway America will be an unsecured senior obligation of
Kingsway America, will rank equally with all Kingsway America's other
unsecured senior indebtedness and will rank senior to all existing and future
subordinated indebtedness of Kingsway America.
    The debentures will only be qualified with securities regulatory
authorities in Canada and will be sold through a syndicate of underwriters led
by Scotia Capital Inc. and including RBC Dominion Securities Inc. The net
proceeds of this offering are expected to be used to provide additional
capital to Kingsway and its indirect and direct subsidiaries to support the
expected growth of business and for general corporate purposes, which will
include the payment of all or a portion of the amount outstanding under its
revolving credit facility.

    This press release is not an offer of the securities for sale in the
United States. The securities being offered have not been, nor will they be,
registered under the United States Securities Act of 1933, as amended, and may
not be offered or sold in the United States absent registration or an
applicable exemption from registration requirements. This press release shall
not constitute an offer to sell or the solicitation of an offer to buy nor
shall there be any sale of the securities in any state in which such offer,
solicitation or sale would be unlawful.

    Forward Looking Statements
    --------------------------
    This press release includes "forward looking statements" that are subject
to risks and uncertainties. For information identifying important factors that
could cause actual results to differ materially from those anticipated in the
forward looking statements, see Kingsway's securities filings, including its
2006 Annual Report under the heading Risks and Uncertainties in the
Management's Discussion and Analysis section. The Company disclaims any
intention or obligation to update or revise any forward looking statements,
whether as a result of new information, future events or otherwise.

    About the Company
    -----------------
    Kingsway is one of the largest truck insurers and non-standard automobile
insurers in North America based on A.M. Best data that we have compiled.
Kingsway's primary business is trucking insurance and the insuring of
automobile risks for drivers who do not meet the criteria for coverage by
standard automobile insurers. The Company currently operates through thirteen
wholly-owned insurance subsidiaries in Canada and the United States. Canadian
subsidiaries include Kingsway General Insurance Company, York Fire & Casualty
Insurance Company and Jevco Insurance Company. United States subsidiaries
include Universal Casualty Company, American Service Insurance Company,
Southern United Fire Insurance Company, Lincoln General Insurance Company,
U.S. Security Insurance Company, American Country Insurance Company, Zephyr
Insurance Company, Mendota Insurance Company, Mendakota Insurance Company and
Avalon Risk Management, Inc. The Company also operates reinsurance
subsidiaries in Barbados and Bermuda.
    The common shares of Kingsway are listed on the Toronto Stock Exchange
and the New York Stock Exchange, under the trading symbol "KFS".

    %SEDAR: 00003152E          %CIK: 0001072627




For further information:

For further information: Shaun Jackson, Executive Vice President and
Chief Financial Officer, Tel: (905) 629-7888, Fax: (905) 629-5008, Web Site:
www.kingsway-financial.com


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