Kingsway Financial Notes Agreement with The Robert Plan Corp.

Toronto-based Kingsway Financial Services Inc. has entered into a program management agreement with The Robert Plan Corporation (‘RPC’). RPC provides underwriting and claims administration services to insurance companies in the United States who seek to transfer their assigned risk obligations to a specialist for a fee. The agreement is effective for new and renewal business on and after Jan. 1, 2006.

“We are pleased to have entered into an agreement with The Robert Plan”, said Bill Star, president and CEO of Kingsway Financial Services Inc. “This transaction is consistent with our strategy of growing our marketshare in the minimum limits non-standard automobile business in the United States. The Robert Plan is a dominant service provider for assigned risks in the U.S. automobile insurance market. We look forward to a long and mutually beneficial relationship with them.”

In certain U.S. States, drivers who cannot obtain insurance in the voluntary market are placed in an assigned risk plan. These insureds are then proportionately assigned to all automobile insurers who do business in that given state.

RPC is a player in the assigned risk automobile market, servicing insurers who seek to transfer their assigned risks and related premiums to another insurer for a fee. Kingsway will be providing underwriting capacity to assume the policies serviced by RPC.

RPC has been in operation since the early 1950’s and since the 1980’s has specialized in the underwriting and servicing of assigned risks for personal and commercial automobile policies.

For the first nine months of 2005, RPC generated gross premiums written of approximately U.S.$185 million and for the year-ended Dec. 31, 2004 generated gross premiums written of approximately U.S.$250 million.