October 26, 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 June 30, 2018
           Filed August 8, 2018
           File No. 001-15204

Dear Mr. Hickey:

        We have reviewed your October 19, 2018 response to our comment letter
and have the
following comment. In our comment, we ask you to provide us with information so
we may
better understand your disclosure.

       Please respond to this comment 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
comment applies to your facts and circumstances, please tell us why in your
response.

      After reviewing your response to this comment, we may have additional
comments. Unless we note otherwise, our references to prior comments are to
comments in our
October 12, 2018 letter.

Form 10-Q for the Quarterly Period Ended June 30, 2018

Notes to Consolidated Financial Statements (Unaudited)
Note 12: Revenue from Contracts with Customers, page 21

1.    You assert in your response to the second bullet of our prior comment
that "the
      quantitative and qualitative aspects, when considered together, support a
conclusion that
      the adjustments do not represent a material misstatement of the
previously issued interim
      financial statements for the three-month period ended March 31, 2018 and
the three and
 William A. Hickey, Jr.
Kingsway Financial Services Inc.
October 26, 2018
Page 2
         six-month periods ended June 30, 2018." Notwithstanding your
assertion, please:
           Represent to us that you will revise your proposed accounting and
disclosure to be
             made in your upcoming Form 10-Q for the quarterly period ended
September 30, 2018
             to reflect your error correction in each of the first two quarters
of 2018. In this regard,
             represent to us that you will disclose therein the effects of the
error on and the restated
             amounts for revenue, loss from continuing operations, net loss and
related per share
             amounts for each of the quarters ended March 31, and June 30, 2018
and the six
             months ended June 30, 2018.
           Represent to us that, in future filings that include these periods,
you will revise the
             financial statements for those quarters and six month period to
correct the error.
           Tell us how you considered the impact of the error discovery as to
whether or not your
             disclosure controls and procedures are effective at September 30,
2018, and provide us
             an analysis if you conclude they are effective pursuant to Item
307 of Regulation S-K.
        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
October 26, 2018 Page 2                                         Office of
Healthcare & Insurance
FirstName LastName