KWY

SEC source: 0001072627-25-000024 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,488,616

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-25-000022 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,898

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

SEC source: 0001072627-25-000020 · form4.xml · nonDerivative · entry 6

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust-MPF

Disclosed balance after: 34,100

F1 · kind: Shares transferred by the reporting person to a trust for which the reporting person serves as trustee and retains voting and investment power over the securities. Accordingly, there has been no change in the reporting person's beneficial ownership.

SEC source: 0001072627-25-000020 · form4.xml · nonDerivative · entry 5

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,488,445

F1 · kind: Shares transferred by the reporting person to a trust for which the reporting person serves as trustee and retains voting and investment power over the securities. Accordingly, there has been no change in the reporting person's beneficial ownership.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-25-000020 · form4.xml · nonDerivative · entry 4

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust-LTF

Disclosed balance after: 34,100

F1 · kind: Shares transferred by the reporting person to a trust for which the reporting person serves as trustee and retains voting and investment power over the securities. Accordingly, there has been no change in the reporting person's beneficial ownership.

SEC source: 0001072627-25-000020 · form4.xml · nonDerivative · entry 3

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,502,545

F1 · kind: Shares transferred by the reporting person to a trust for which the reporting person serves as trustee and retains voting and investment power over the securities. Accordingly, there has been no change in the reporting person's beneficial ownership.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-25-000020 · form4.xml · nonDerivative · entry 2

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust-GEF

Disclosed balance after: 34,100

F1 · kind: Shares transferred by the reporting person to a trust for which the reporting person serves as trustee and retains voting and investment power over the securities. Accordingly, there has been no change in the reporting person's beneficial ownership.

SEC source: 0001072627-25-000020 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,516,645

F1 · kind: Shares transferred by the reporting person to a trust for which the reporting person serves as trustee and retains voting and investment power over the securities. Accordingly, there has been no change in the reporting person's beneficial ownership.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001104659-25-091309 · tm2526479-1_4seq1.xml · nonDerivative · entry 7

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

Stilwell Associates, L.P. · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 590,410

F2 · kind: This Form 4 reports the following sales on September 16, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 11,941 shares at $14.4000; (b) Stilwell Activist Fund, L.P. ("SAF") sold 2,106 shares at $14.4000; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,953 shares at $14.4000. This Form 4 also reports the following sales on September 17, 2025: (a) SAI sold 28,657 shares at $14.4700; (b) SAF sold 5,055 shares at $14.4700; and (c) SVP VII sold 14,288 shares at $14.4700.

F5 · ownership.nature: 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.

SEC source: 0001104659-25-091309 · tm2526479-1_4seq1.xml · nonDerivative · entry 6

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

Stilwell Associates, L.P. · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 457,181

F2 · kind: This Form 4 reports the following sales on September 16, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 11,941 shares at $14.4000; (b) Stilwell Activist Fund, L.P. ("SAF") sold 2,106 shares at $14.4000; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,953 shares at $14.4000. This Form 4 also reports the following sales on September 17, 2025: (a) SAI sold 28,657 shares at $14.4700; (b) SAF sold 5,055 shares at $14.4700; and (c) SVP VII sold 14,288 shares at $14.4700.

F4 · ownership.nature: 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.

SEC source: 0001104659-25-091309 · tm2526479-1_4seq1.xml · nonDerivative · entry 5

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

Stilwell Associates, L.P. · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 3,550,382

F2 · kind: This Form 4 reports the following sales on September 16, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 11,941 shares at $14.4000; (b) Stilwell Activist Fund, L.P. ("SAF") sold 2,106 shares at $14.4000; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,953 shares at $14.4000. This Form 4 also reports the following sales on September 17, 2025: (a) SAI sold 28,657 shares at $14.4700; (b) SAF sold 5,055 shares at $14.4700; and (c) SVP VII sold 14,288 shares at $14.4700.

F3 · ownership.nature: 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.

SEC source: 0001104659-25-091309 · tm2526479-1_4seq1.xml · nonDerivative · entry 4

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

Stilwell Associates, L.P. · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 604,698

F2 · kind: This Form 4 reports the following sales on September 16, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 11,941 shares at $14.4000; (b) Stilwell Activist Fund, L.P. ("SAF") sold 2,106 shares at $14.4000; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,953 shares at $14.4000. This Form 4 also reports the following sales on September 17, 2025: (a) SAI sold 28,657 shares at $14.4700; (b) SAF sold 5,055 shares at $14.4700; and (c) SVP VII sold 14,288 shares at $14.4700.

F5 · ownership.nature: 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.

SEC source: 0001104659-25-091309 · tm2526479-1_4seq1.xml · nonDerivative · entry 3

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

Stilwell Associates, L.P. · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 462,236

F2 · kind: This Form 4 reports the following sales on September 16, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 11,941 shares at $14.4000; (b) Stilwell Activist Fund, L.P. ("SAF") sold 2,106 shares at $14.4000; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,953 shares at $14.4000. This Form 4 also reports the following sales on September 17, 2025: (a) SAI sold 28,657 shares at $14.4700; (b) SAF sold 5,055 shares at $14.4700; and (c) SVP VII sold 14,288 shares at $14.4700.

F4 · ownership.nature: 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.

SEC source: 0001104659-25-091309 · tm2526479-1_4seq1.xml · nonDerivative · entry 2

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

Stilwell Associates, L.P. · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 3,579,039

F2 · kind: This Form 4 reports the following sales on September 16, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 11,941 shares at $14.4000; (b) Stilwell Activist Fund, L.P. ("SAF") sold 2,106 shares at $14.4000; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,953 shares at $14.4000. This Form 4 also reports the following sales on September 17, 2025: (a) SAI sold 28,657 shares at $14.4700; (b) SAF sold 5,055 shares at $14.4700; and (c) SVP VII sold 14,288 shares at $14.4700.

F3 · ownership.nature: 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.

SEC source: 0001072627-25-000018 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,530,745

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-25-000017 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,791

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

SEC source: 0001104659-25-089153 · tm2525816-1_4seq1.xml · nonDerivative · entry 4

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

Stilwell Associates, L.P. · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 610,651

F2 · kind: 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.

F5 · ownership.nature: 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.

SEC source: 0001104659-25-089153 · tm2525816-1_4seq1.xml · nonDerivative · entry 3

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

Stilwell Associates, L.P. · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 464,342

F2 · kind: 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.

F4 · ownership.nature: 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.

SEC source: 0001104659-25-089153 · tm2525816-1_4seq1.xml · nonDerivative · entry 2

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

Stilwell Associates, L.P. · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 3,590,980

F2 · kind: 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 · ownership.nature: 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.

SEC source: 0001072627-25-000016 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,682

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

SEC source: 0001072627-25-000015 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,530,571

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001104659-25-083161 · tm2524429-1_4seq1.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 618,156

F2 · kind: This Form 4 reports the following sales on August 22, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 44,772 shares at $14.1784; (b) Stilwell Activist Fund, L.P. ("SAF") sold 7,642 shares at $14.1784; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 22,586 shares at $14.1784.

F5 · ownership.nature: 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.

SEC source: 0001104659-25-083161 · tm2524429-1_4seq1.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 466,893

F2 · kind: This Form 4 reports the following sales on August 22, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 44,772 shares at $14.1784; (b) Stilwell Activist Fund, L.P. ("SAF") sold 7,642 shares at $14.1784; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 22,586 shares at $14.1784.

F4 · ownership.nature: 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.

SEC source: 0001104659-25-083161 · tm2524429-1_4seq1.xml · nonDerivative · entry 2

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 3,605,924

F2 · kind: This Form 4 reports the following sales on August 22, 2025: (a) Stilwell Activist Investments, L.P. ("SAI") sold 44,772 shares at $14.1784; (b) Stilwell Activist Fund, L.P. ("SAF") sold 7,642 shares at $14.1784; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 22,586 shares at $14.1784.

F3 · ownership.nature: 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.

SEC source: 0001072627-25-000014 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,530,398

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-25-000013 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,575

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

SEC source: 0001104659-25-081007 · tm2524039-1_4seq1.xml · nonDerivative · entry 7

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 640,742

F2 · kind: This Form 4 reports the following sales: on August 18, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 23,779 shares at $13.95, and 18,835 shares at $14.1631; (b) Stilwell Activist Fund, L.P. ("SAF") sold 4,098 shares at $13.95, and 3,184 shares at $14.1631; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 12,123 shares at $13.95, and 9,410 shares at $14,1631.

F5 · ownership.nature: 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.

SEC source: 0001104659-25-081007 · tm2524039-1_4seq1.xml · nonDerivative · entry 6

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 474,535

F2 · kind: This Form 4 reports the following sales: on August 18, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 23,779 shares at $13.95, and 18,835 shares at $14.1631; (b) Stilwell Activist Fund, L.P. ("SAF") sold 4,098 shares at $13.95, and 3,184 shares at $14.1631; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 12,123 shares at $13.95, and 9,410 shares at $14,1631.

F4 · ownership.nature: 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.

SEC source: 0001104659-25-081007 · tm2524039-1_4seq1.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 3,650,696

F2 · kind: This Form 4 reports the following sales: on August 18, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 23,779 shares at $13.95, and 18,835 shares at $14.1631; (b) Stilwell Activist Fund, L.P. ("SAF") sold 4,098 shares at $13.95, and 3,184 shares at $14.1631; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 12,123 shares at $13.95, and 9,410 shares at $14,1631.

F3 · ownership.nature: 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.

SEC source: 0001104659-25-081007 · tm2524039-1_4seq1.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 650,152

F2 · kind: This Form 4 reports the following sales: on August 18, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 23,779 shares at $13.95, and 18,835 shares at $14.1631; (b) Stilwell Activist Fund, L.P. ("SAF") sold 4,098 shares at $13.95, and 3,184 shares at $14.1631; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 12,123 shares at $13.95, and 9,410 shares at $14,1631.

F5 · ownership.nature: 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.

SEC source: 0001104659-25-081007 · tm2524039-1_4seq1.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 477,719

F2 · kind: This Form 4 reports the following sales: on August 18, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 23,779 shares at $13.95, and 18,835 shares at $14.1631; (b) Stilwell Activist Fund, L.P. ("SAF") sold 4,098 shares at $13.95, and 3,184 shares at $14.1631; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 12,123 shares at $13.95, and 9,410 shares at $14,1631.

F4 · ownership.nature: 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.

SEC source: 0001104659-25-081007 · tm2524039-1_4seq1.xml · nonDerivative · entry 2

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 3,669,531

F2 · kind: This Form 4 reports the following sales: on August 18, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 23,779 shares at $13.95, and 18,835 shares at $14.1631; (b) Stilwell Activist Fund, L.P. ("SAF") sold 4,098 shares at $13.95, and 3,184 shares at $14.1631; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 12,123 shares at $13.95, and 9,410 shares at $14,1631.

F3 · ownership.nature: 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.

SEC source: 0001072627-25-000012 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,530,222

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-25-000010 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,464

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

SEC source: 0001127602-25-019261 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,356

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

SEC source: 0001127602-25-019260 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,530,048

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-25-018383 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,529,876

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-25-018381 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,248

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

SEC source: 0001104659-25-064846 · tm2519640-1_4seq1.xml · nonDerivative · entry 7

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 662,275

F2 · kind: This Form 4 reports the following sales: on June 27, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 85,191 shares at $14.0327; (b) Stilwell Activist Fund, L.P. ("SAF") sold 11,224 shares at $14.0327; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 31,828 shares at $14.0327; and on June 30, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 8,319 shares at $13.90497; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,896 shares at $13.90497; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 18,763 shares at $13.90497.

F5 · ownership.nature: 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.

SEC source: 0001104659-25-064846 · tm2519640-1_4seq1.xml · nonDerivative · entry 6

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 481,817

F2 · kind: This Form 4 reports the following sales: on June 27, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 85,191 shares at $14.0327; (b) Stilwell Activist Fund, L.P. ("SAF") sold 11,224 shares at $14.0327; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 31,828 shares at $14.0327; and on June 30, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 8,319 shares at $13.90497; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,896 shares at $13.90497; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 18,763 shares at $13.90497.

F4 · ownership.nature: 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.

SEC source: 0001104659-25-064846 · tm2519640-1_4seq1.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 3,693,310

F2 · kind: This Form 4 reports the following sales: on June 27, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 85,191 shares at $14.0327; (b) Stilwell Activist Fund, L.P. ("SAF") sold 11,224 shares at $14.0327; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 31,828 shares at $14.0327; and on June 30, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 8,319 shares at $13.90497; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,896 shares at $13.90497; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 18,763 shares at $13.90497.

F3 · ownership.nature: 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.

SEC source: 0001104659-25-064846 · tm2519640-1_4seq1.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 681,038

F2 · kind: This Form 4 reports the following sales: on June 27, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 85,191 shares at $14.0327; (b) Stilwell Activist Fund, L.P. ("SAF") sold 11,224 shares at $14.0327; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 31,828 shares at $14.0327; and on June 30, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 8,319 shares at $13.90497; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,896 shares at $13.90497; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 18,763 shares at $13.90497.

F5 · ownership.nature: 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.

SEC source: 0001104659-25-064846 · tm2519640-1_4seq1.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 487,713

F2 · kind: This Form 4 reports the following sales: on June 27, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 85,191 shares at $14.0327; (b) Stilwell Activist Fund, L.P. ("SAF") sold 11,224 shares at $14.0327; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 31,828 shares at $14.0327; and on June 30, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 8,319 shares at $13.90497; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,896 shares at $13.90497; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 18,763 shares at $13.90497.

F4 · ownership.nature: 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.

SEC source: 0001104659-25-064846 · tm2519640-1_4seq1.xml · nonDerivative · entry 2

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 3,701,629

F2 · kind: This Form 4 reports the following sales: on June 27, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 85,191 shares at $14.0327; (b) Stilwell Activist Fund, L.P. ("SAF") sold 11,224 shares at $14.0327; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 31,828 shares at $14.0327; and on June 30, 2025 (a) Stilwell Activist Investments, L.P. ("SAI") sold 8,319 shares at $13.90497; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,896 shares at $13.90497; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 18,763 shares at $13.90497.

F3 · ownership.nature: 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.

SEC source: 0001127602-25-017549 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,137

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

SEC source: 0001127602-25-017548 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,529,697

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-25-016176 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,023

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

SEC source: 0001127602-25-016174 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,529,516

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-25-014918 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,529,321

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-25-014914 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 134,999

F1 · shares: The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

F2 · balance_after: Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.