FORM 4 [ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).         
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES
                                                                                  
OMB APPROVAL
OMB Number: 3235-0287
Estimated average burden
hours per response...
0.5
                      
Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940
                      
1. Name and Address of Reporting Person * STILWELL JOSEPH 2. Issuer Name and Ticker or Trading Symbol KINGSWAY FINANCIAL SERVICES INC [ KFS ] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable)__X__ Director                    __X__ 10% Owner
_____ Officer (give title below)    _____ Other (specify below)
(Last)         (First)         (Middle)
200 CALLE DEL SANTO CRISTO
3. Date of Earliest Transaction (MM/DD/YYYY)
9/13/2021
(Street)
SAN JUAN, PR 00901
(City)       (State)       (Zip)
4. If Amendment, Date Original Filed (MM/DD/YYYY)
 
6. Individual or Joint/Group Filing (Check Applicable Line) ___ Form filed by One Reporting Person
_ X _ Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price
Common Stock                 162500 (1) D   
Common Stock  9/13/2021    P(2)    579  A $5.35  939242  I  See footnote (3)
Common Stock  9/13/2021    P(2)    909  A $5.35  567880  I  See footnote (4)
Common Stock  9/13/2021    P(2)    6048  A $5.35  4517088  I  See footnote (5)
Common Stock  9/13/2021    P(2)    1464  A $5.35  819515  I  See footnote (6)

Table II - Derivative Securities Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security 3. Trans. Date 3A. Deemed Execution Date, if any 4. Trans. Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
6. Date Exercisable and Expiration Date 7. Title and Amount of Securities Underlying Derivative Security
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares

Explanation of Responses:
(1)  These are shares owned directly by Joseph Stilwell.
(2)  This Form 4 reports the following acquisitions on September 13, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,048 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 909 shares at $5.35 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,464 shares at $5.35 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 579 shares at $5.35 USD per share.
(3)  These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
(4)  These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
(5)  These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
(6)  These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Reporting Owners
Reporting Owner Name / Address
Relationships
Director 10% Owner Officer Other
STILWELL JOSEPH
200 CALLE DEL SANTO CRISTO
SAN JUAN, PR 00901
X X

Stilwell Value LLC
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X

STILWELL ASSOCIATES L P
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X

Stilwell Activist Fund, L.P.
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X

Stilwell Activist Investments, L.P.
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X

Stilwell Value Partners VII, L.P.
111 BROADWAY, 12TH FLOOR
NEW YORK, NY 10006

X


Signatures
/s/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell 9/15/2021
**Signature of Reporting Person Date
/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC 9/15/2021
**Signature of Reporting Person Date
/s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P. 9/15/2021
**Signature of Reporting Person Date
/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P. 9/15/2021
**Signature of Reporting Person Date
/s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P. 9/15/2021
**Signature of Reporting Person Date
/s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P. 9/15/2021
**Signature of Reporting Person Date
Kingsway Financial Servi... (NYSE:KFS)
Historical Stock Chart
From Sep 2021 to Oct 2021 Click Here for more Kingsway Financial Servi... Charts.
Kingsway Financial Servi... (NYSE:KFS)
Historical Stock Chart
From Oct 2020 to Oct 2021 Click Here for more Kingsway Financial Servi... Charts.