X0508 4 2025-12-08 0 0001072627 KINGSWAY FINANCIAL SERVICES INC KFS 0001113303 Stilwell Joseph 200 CALLE DEL SANTO CRISTO SAN JUAN PR 00901 PUERTO RICO 1 0 1 0 0001397076 Stilwell Value LLC 111 BROADWAY, 12TH FLOOR NEW YORK NY 10006 0 0 1 0 0000913960 Stilwell Associates, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK NY 10006 0 0 1 0 0001564452 Stilwell Activist Fund, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK NY 10006 0 0 1 0 0001573720 Stilwell Activist Investments, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK NY 10006 0 0 1 0 0001555931 Stilwell Value Partners VII, L.P. 111 BROADWAY, 12TH FLOOR NEW YORK NY 10006 0 0 1 0 0 Common Stock 162500 D Common Stock 2025-12-08 4 S 0 35000 12.82 D 666904 I See footnote Common Stock 2025-12-09 4 S 0 20000 12.80 D 646904 I See footnote Common Stock 3550382 I See footnote Common Stock 457181 I See footnote Common Stock 590410 I See footnote Class D Preferred Stock 9.5 2025-05-07 2032-05-07 Common Stock 52631 20000 I See footnote Class C Preferred Stock 9.5 2025-02-12 2032-02-12 Common Stock 88421 33600 I See footnote Class C Preferred Stock 9.5 2025-02-12 2032-02-12 Common Stock 16842 6400 I See footnote These are shares owned directly by Joseph Stilwell. This Form 4 reports the following sales: on December 8, 2025 Stilwell Associates, L.P. ("Associates") sold 35,000 shares at $12.82; and on December 9, 2025 Associates sold 20,000 shares at $12.80. 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. These are shares owned directly by Stilwell Activist Investments, L.P. ("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. These are shares owned directly by Stilwell Activist Fund, L.P. ("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. These are shares owned directly by Stilwell Value Partners VII, L.P. ("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. 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. 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. /s/ Debra Rouse as Attorney-in-Fact for Joseph Stilwell 2025-12-10 /s/ Debra Rouse as Attorney-in-Fact for Stilwell Value LLC 2025-12-10 /s/ Debra Rouse as Attorney-in-Fact for Stilwell Associates, L.P. 2025-12-10 /s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Fund, L.P. 2025-12-10 /s/ Debra Rouse as Attorney-in-Fact for Stilwell Activist Investments, L.P. 2025-12-10 /s/ Debra Rouse as Attorney-in-Fact for Stilwell Value Partners VII, L.P. 2025-12-10