SecProbe.io

October 15, 2018
John Fitzgerald
President and Chief Executive Officer
Kingsway Financial Services Inc.
45 St. Clair Avenue West, Suite 400
Toronto, Ontario, Canada M4V 1K9
Re:Kingsway Financial Services Inc.
Registration Statement on Form S-4
Filed September 28, 2018
File No. 333-227577
Dear Mr. Fitzgerald:
            We have limited our review of your registration statement to those issues we have
addressed in our comments.  In some of our comments, we may ask you to provide us with
information so we may better understand your disclosure.
            Please respond to this letter by amending your registration statement and providing the
requested information.  If you do not believe our comments apply to your facts and
circumstances or do not believe an amendment is appropriate, please tell us why in your
response.
            After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.
Registration Statement on Form S-4
Where You Can Find More Information, page 37
1.The aggregate market value of your common equity held by non-affiliates appears to be
below the minimum public float requirements of General Instruction I.B.1 of Form S-3.
As such, it appears you are not eligible to incorporate information by reference.  Please
amend your registration statement to include the required information within the filing, or
alternatively, advise us why you believe you are eligible to incorporate by reference.
2.Please revise your filing to include the information listed below:
•Audited financial statements covering each of the three years in the period ended

 FirstName LastNameJohn Fitzgerald
 Comapany NameKingsway Financial Services Inc.
 October 15, 2018 Page 2
 FirstName LastName
John Fitzgerald
Kingsway Financial Services Inc.
October 15, 2018
Page 2
December 31, 2017 that are recast to retrospectively reflect your discontinued
operations resulting from the pending sale of your Insurance segment consistent with
the guidance in ASC 205-10-45-3.
•Revised selected financial data for each of the five years in the period ended
December 31, 2017 that are recast to retrospectively reflect your Insurance segment
as discontinued operations.
•Revised results of operations discussions in Management's Discussion and Analysis
covering each of the three years in the period ended December 31, 2017 that
appropriately retrospectively reflects your Insurance segment as a discontinued
operation.

In addition, ensure that the disclosure and classification revisions promised in response to
our previous comments in connection with our review of your Form 10-K for the fiscal
year ended December 31, 2017 and Forms 10-Q for the quarterly periods ended March 31
and June 30, 2018 are reflected in your recasted financial statements.
General
3.We note that there are outstanding comments on your Form 10-K for the fiscal year ended
December 31, 2017, and your Form 10-Qs for the quarters ended March 31, 2018 and
June 30, 2018.  Please be advised that we will not be in a position to declare
your registration statement effective until all comments on your Exchange Act filings are
resolved.
            We remind you that the company and its management are responsible for the accuracy
and adequacy of their disclosures, notwithstanding any review, comments, action or absence of
action by the staff.
            Refer to Rules 460 and 461 regarding requests for acceleration.  Please allow adequate
time for us to review any amendment prior to the requested effective date of the registration
statement.
            You may contact Mark Brunhofer at 202-551-3638 or Jim Rosenberg at 202-551-3679 if
you have questions regarding comments on the financial statements and related matters.  Please
contact Dorrie Yale at 202-551-8776 or Joe McCann at 202-551-6262 with any other questions.
Sincerely,
Division of Corporation Finance
Office of Healthcare & Insurance
cc:       Eric Orsic