Stilwell Joseph - 08 Sep 2025 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Role
Director, 10%+ Owner
Signature
/s/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell
Issuer symbol
KFS
Transactions as of
08 Sep 2025
Net transactions value
-$360,250
Form type
4
Filing time
10 Sep 2025, 18:36:42 UTC
Previous filing
26 Aug 2025
Next filing
11 Sep 2025
SEC
View on sec.gov

Reporting Owners (6)

Name Relationship Address Signature Signature date CIK
Stilwell Joseph Director, 10%+ Owner 200 CALLE DEL SANTO CRISTO, SAN JUAN, PUERTO RICO /s/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell 10 Sep 2025 0001113303
Stilwell Value LLC 10%+ Owner 111 BROADWAY, 12TH FLOOR, NEW YORK /s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC 10 Sep 2025 0001397076
Stilwell Associates, L.P. 10%+ Owner 111 BROADWAY, 12TH FLOOR, NEW YORK /s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P. 10 Sep 2025 0000913960
Stilwell Activist Fund, L.P. 10%+ Owner 111 BROADWAY, 12TH FLOOR, NEW YORK /s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P. 10 Sep 2025 0001564452
Stilwell Activist Investments, L.P. 10%+ Owner 111 BROADWAY, 12TH FLOOR, NEW YORK /s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P. 10 Sep 2025 0001573720
Stilwell Value Partners VII, L.P. 10%+ Owner 111 BROADWAY, 12TH FLOOR, NEW YORK /s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P. 10 Sep 2025 0001555931

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction KFS Common Stock Sale $215,343 -14,944 -0.41% $14.41 3,590,980 08 Sep 2025 See footnote F2, F3
transaction KFS Common Stock Sale $36,760 -2,551 -0.55% $14.41 464,342 08 Sep 2025 See footnote F2, F4
transaction KFS Common Stock Sale $108,147 -7,505 -1.2% $14.41 610,651 08 Sep 2025 See footnote F2, F5
holding KFS Common Stock 162,500 08 Sep 2025 Direct F1
holding KFS Common Stock 701,904 08 Sep 2025 See footnote F6

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
holding KFS Class D Preferred Stock 20,000 08 Sep 2025 Common Stock 52,631 $9.50 See footnote F6, F7
holding KFS Class C Preferred Stock 33,600 08 Sep 2025 Common Stock 88,421 $9.50 See footnote F3, F8
holding KFS Class C Preferred Stock 6,400 08 Sep 2025 Common Stock 16,842 $9.50 See footnote F4, F8
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 These are shares owned directly by Joseph Stilwell.
F2 This Form 4 reports the following sales on September 8, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 14,944 shares at $14.4100; (b) Stilwell Activist Fund, L.P. ("SAF") sold 2,551 shares at $14.4100; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 7,505 shares at $14.4100.
F3 These are shares owned directly by SAI 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 SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.
F4 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.
F5 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.
F6 These are shares owned directly by Stilwell Associates, L.P. ("Associates") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of 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.
F7 The shares of Class D Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class D Preferred Stock, subject to customary adjustments. All outstanding shares of Class D Preferred Stock shall be redeemed by the Company on May 7, 2032.
F8 The shares of Class C Preferred Stock of the Company have a stated value of $25 per share and are convertible at any time into shares of Common Stock at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class C Preferred Stock, subject to customary adjustments. All outstanding shares of Class C Preferred Stock shall be redeemed by the Company on February 12, 2032.