August 8, 2018

William A. Hickey, Jr.
Executive Vice President and Chief Financial Officer
Kingsway Financial Services Inc.
45 St. Clair Avenue West, Suite 400
Toronto, Ontario M4V 1K9
Canada

       Re: Kingsway Financial Services Inc.
           Form 10-K for the Fiscal Year Ended December 31, 2017
           Filed March 16, 2018
           Form 10-Q for the Quarterly Period Ended March 31, 2018
           Filed May 14, 2018
           File No. 001-15204

Dear Mr. Hickey:

        We have reviewed your July 12, 2018 response to our comment letter and
have the
following comments. In our comments, we ask you to provide us with information
so we may
better understand your disclosure.

       Please respond to these comments within 10 business days by providing
the requested
information or advise us as soon as possible when you will respond. If you do
not believe our
comments apply to your facts and circumstances, please tell us why in your
response.

       After reviewing your response to these comments, we may have additional
comments. Unless we note otherwise, our references to prior comments are to
comments in our
June 27, 2018 letter.

Form 10-Q for the Quarterly Period Ended March 31, 2018

Notes to Consolidated Financial Statements
Note 12: Revenue From Contracts with Customers, page 19

1.    We acknowledge your response to prior comment 3 and your May 23, 2018
response to
      comment 6 from our April 25, 2018 letter. Regarding your accounting for
revenue under
      your IWS vehicle service agreements please address the following,
referencing the
      authoritative literature you relied upon to support your accounting under
ASC 606:
 William A. Hickey, Jr.
Kingsway Financial Services Inc.
August 8, 2018
Page 2

             Tell us how you determined that the sale of vehicle services
agreements resulting in
             the administrative fees upon sale are separate and distinct from
the performance
             obligation to administer future claims.
             Tell us how you allocate transaction price between the
administrative fees from the
             sale of these agreements and the fees to administer future claims.
2.       We acknowledge your response to prior comment 5. Regarding your
response to the
         second bullet of that comment, your disclosure indicates that,
separate from the
         commission, there appear to be two components of the PWSC's contracts
that you treat as
         separate performance obligations under ASC 606; a Homebuilder warranty
administrative
         fee and a Homebuilder warranty service fee. Please address the
following, referencing the
         authoritative literature you relied upon to support your accounting
under ASC 606:
           Tell us how you determined that the administrative fee is separate
and distinct from
             the service fee.
           Tell us how you allocate transaction price between the
administrative fee from the sale
             of these agreements and the fees to administer future claims.
        You may contact Mark Brunhofer at (202) 551-3638 or Jim Rosenberg at
(202) 551-
3679 if you have any questions.



FirstName LastNameWilliam A. Hickey, Jr.                      Sincerely,
Comapany NameKingsway Financial Services Inc.
                                                              Division of
Corporation Finance
August 8, 2018 Page 2                                         Office of
Healthcare & Insurance
FirstName LastName