REGISTRATION RIGHTS AGREEMENT

Dated as of January 28, 2004

among

KINGSWAY AMERICA INC.,

KINGSWAY FINANCIAL SERVICES INC.,

as Guarantor

and

KEEFE, BRUYETTE & WOODS, INC.

as Initial Purchaser

REGISTRATION RIGHTS AGREEMENT

REGISTRATION RIGHTS AGREEMENT (the Agreement) dated as of January 28, 2004 among Kingsway America Inc., a Delaware corporation (the Company), Kingsway Financial Services Inc., a company organized under the laws of Ontario, Canada (the Guarantor), Keefe, Bruyette & Woods, Inc. (the Representative) and the other parties referred to in Annex A hereto, if any (each, an Initial Purchaser and collectively, the Initial Purchasers).

This Agreement is made pursuant to the Purchase Agreement, dated January 23, 2004, by and among the Company, the Guarantor and the Initial Purchasers (the Purchase Agreement), which provides for the sale by the Company to the Initial Purchasers of US$100,000,000 aggregate principal amount of the Companys 7.50% Senior Notes due 2014 (the Notes). The Notes will be fully and unconditionally guaranteed as to principal, premium, if any, and interest pursuant to the Indenture by the Guarantor (the Guarantee). In order to induce the Initial Purchasers to enter into the Purchase Agreement and in satisfaction of a condition to the Initial Purchasers obligations thereunder, the Company and the Guarantor have agreed to provide to the Initial Purchasers and their respective direct and indirect transferees and assigns the registration rights set forth in this Agreement. The execution and delivery of this Agreement is a condition to the closing under the Purchase Agreement.

In consideration of the foregoing, the parties hereto agree as follows:

1. Definitions. As used in this Agreement, the following capitalized defined terms shall have the following meanings:

1933 Act shall mean the Securities Act of 1933, as amended from time to time, and the rules and regulations of the SEC promulgated thereunder.

1934 Act shall mean the Securities Exchange Act of 1934, as amended from time to time, and the rules and regulations of the SEC promulgated thereunder.

Special Interest shall have the meaning set forth in Section 2(e) hereof.

Closing Time shall mean January 28, 2004.

Company shall have the meaning set forth in the preamble to this Agreement.

Depositary shall mean The Depository Trust Company, or any other depositary appointed by the Company, including any agent thereof; provided, however, that any such depositary must at all times have an address in the Borough of Manhattan, The City of New York.

Event Date shall have the meaning set forth in Section 2(e) hereof.

Exchange Offer shall mean the exchange offer by the Company and the Guarantor of Exchange Securities for Registrable Securities pursuant to Section 2(a) hereof.

Exchange Offer Registration shall mean a registration under the 1933 Act effected pursuant to Section 2(a) hereof.

Exchange Offer Registration Statement shall mean any exchange offer registration statement of the Company and the Guarantor on Form F-4 (or, if applicable, on another appropriate form) covering the Registrable Securities, and all amendments and supplements to such registration statement, in each case including the Prospectus contained therein, all exhibits thereto and all material incorporated or deemed to be incorporated by reference therein.

Exchange Securities shall mean the notes and the guarantee in respect thereof, issued by the Company and the Guarantor under the Indenture with terms identical to the Securities and the Guarantee (except that (i) interest thereon shall accrue from the last date to which interest has been paid or duly provided for on the Securities or, if no such interest has been paid or duly provided for, from the Interest Accrual Date, (ii) provisions relating to an increase in the stated rate of interest thereon upon the occurrence of a Registration Default shall be eliminated and (iii) the transfer restrictions and legends relating to restrictions on ownership and transfer thereof as a result of the issuance of the Securities without registration under the 1933 Act shall be eliminated, to be offered to Holders of Registrable Securities in exchange for Registrable Securities pursuant to the Exchange Offer.

Guarantee shall have the meaning set forth in the preamble to this Agreement.

Guarantor shall have the meaning set forth in the preamble to this Agreement.

Holders shall mean (i) the Initial Purchasers, for so long as they own any Registrable Securities, and each of their respective successors, assigns and direct and indirect transferees who become registered owners of Registrable Securities under the Indenture and (ii) each Participating Broker-Dealer that holds Exchange Securities for so long as such Participating Broker-Dealer is required to deliver a prospectus meeting the requirements of the 1933 Act in connection with any resale of such Exchange Securities.

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