KWY

SEC source: 0001104659-22-064221 · tm2216766-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 928,237

F3 · kind: This Form 4 reports the following acquisitions on May 20, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 4,690 shares at $5.30; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 883 shares at $5.30; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,516 shares at $5.30; and on May 23, 2022: (a) SAI acquired 1,889 shares at $5.3874 and (b) SVP VII acquired 611 shares at $5.3874.

F6 · 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: 0001104659-22-064221 · tm2216766-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 643,728

F3 · kind: This Form 4 reports the following acquisitions on May 20, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 4,690 shares at $5.30; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 883 shares at $5.30; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,516 shares at $5.30; and on May 23, 2022: (a) SAI acquired 1,889 shares at $5.3874 and (b) SVP VII acquired 611 shares at $5.3874.

F5 · 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: 0001104659-22-064221 · tm2216766-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,947,346

F3 · kind: This Form 4 reports the following acquisitions on May 20, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 4,690 shares at $5.30; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 883 shares at $5.30; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,516 shares at $5.30; and on May 23, 2022: (a) SAI acquired 1,889 shares at $5.3874 and (b) SVP VII acquired 611 shares at $5.3874.

F4 · ownership.nature: 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.

SEC source: 0001104659-22-062874 · tm2216116d1_4seq1.xml · nonDerivative · entry 8

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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 926,721

F3 · kind: This Form 4 reports the following acquisitions on May 17, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.40; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.40; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.40; and on May 18, 2022: (a) SAI acquired 6,616 shares at $5.35; (b) SAF acquired 1,245 shares at $5.35; and (c) SVP VII acquired 2,139 shares at $5.35.

F6 · 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: 0001104659-22-062874 · tm2216116d1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 642,845

F3 · kind: This Form 4 reports the following acquisitions on May 17, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.40; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.40; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.40; and on May 18, 2022: (a) SAI acquired 6,616 shares at $5.35; (b) SAF acquired 1,245 shares at $5.35; and (c) SVP VII acquired 2,139 shares at $5.35.

F5 · 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: 0001104659-22-062874 · tm2216116d1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,942,656

F3 · kind: This Form 4 reports the following acquisitions on May 17, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.40; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.40; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.40; and on May 18, 2022: (a) SAI acquired 6,616 shares at $5.35; (b) SAF acquired 1,245 shares at $5.35; and (c) SVP VII acquired 2,139 shares at $5.35.

F4 · ownership.nature: 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.

SEC source: 0001127602-22-014994 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 91,094

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 20,000 shares of restricted stock granted on February 26, 2021 and 32,754 shares of restricted stock granted on December 3, 2021.

SEC source: 0001127602-22-014996 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,920,445

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 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001104659-22-062874 · tm2216116d1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 924,582

F3 · kind: This Form 4 reports the following acquisitions on May 17, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.40; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.40; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.40; and on May 18, 2022: (a) SAI acquired 6,616 shares at $5.35; (b) SAF acquired 1,245 shares at $5.35; and (c) SVP VII acquired 2,139 shares at $5.35.

F6 · 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: 0001104659-22-062874 · tm2216116d1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 641,600

F3 · kind: This Form 4 reports the following acquisitions on May 17, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.40; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.40; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.40; and on May 18, 2022: (a) SAI acquired 6,616 shares at $5.35; (b) SAF acquired 1,245 shares at $5.35; and (c) SVP VII acquired 2,139 shares at $5.35.

F5 · 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: 0001104659-22-062874 · tm2216116d1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,936,040

F3 · kind: This Form 4 reports the following acquisitions on May 17, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.40; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.40; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.40; and on May 18, 2022: (a) SAI acquired 6,616 shares at $5.35; (b) SAF acquired 1,245 shares at $5.35; and (c) SVP VII acquired 2,139 shares at $5.35.

F4 · ownership.nature: 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.

SEC source: 0001104659-22-061941 · tm2215866-1_4seq1.xml · nonDerivative · entry 8

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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 922,443

F3 · kind: This Form 4 reports the following acquisitions on May 13, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.41; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.41; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.41; and on May 16, 2022: (a) SAI acquired 6,616 shares at $5.3983; (b) SAF acquired 1,245 shares at $5.3983; and (c) SVP VII acquired 2,139 shares at $5.3983.

F6 · 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: 0001104659-22-061941 · tm2215866-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 640,355

F3 · kind: This Form 4 reports the following acquisitions on May 13, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.41; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.41; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.41; and on May 16, 2022: (a) SAI acquired 6,616 shares at $5.3983; (b) SAF acquired 1,245 shares at $5.3983; and (c) SVP VII acquired 2,139 shares at $5.3983.

F5 · 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: 0001104659-22-061941 · tm2215866-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,929,424

F3 · kind: This Form 4 reports the following acquisitions on May 13, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.41; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.41; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.41; and on May 16, 2022: (a) SAI acquired 6,616 shares at $5.3983; (b) SAF acquired 1,245 shares at $5.3983; and (c) SVP VII acquired 2,139 shares at $5.3983.

F4 · ownership.nature: 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.

SEC source: 0001104659-22-061941 · tm2215866-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 920,304

F3 · kind: This Form 4 reports the following acquisitions on May 13, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.41; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.41; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.41; and on May 16, 2022: (a) SAI acquired 6,616 shares at $5.3983; (b) SAF acquired 1,245 shares at $5.3983; and (c) SVP VII acquired 2,139 shares at $5.3983.

F6 · 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: 0001104659-22-061941 · tm2215866-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 639,110

F3 · kind: This Form 4 reports the following acquisitions on May 13, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.41; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.41; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.41; and on May 16, 2022: (a) SAI acquired 6,616 shares at $5.3983; (b) SAF acquired 1,245 shares at $5.3983; and (c) SVP VII acquired 2,139 shares at $5.3983.

F5 · 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: 0001104659-22-061941 · tm2215866-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,922,808

F3 · kind: This Form 4 reports the following acquisitions on May 13, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.41; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.41; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.41; and on May 16, 2022: (a) SAI acquired 6,616 shares at $5.3983; (b) SAF acquired 1,245 shares at $5.3983; and (c) SVP VII acquired 2,139 shares at $5.3983.

F4 · ownership.nature: 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.

SEC source: 0001104659-22-060300 · tm2215529-1_4seq1.xml · nonDerivative · entry 8

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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 918,165

F3 · kind: This Form 4 reports the following acquisitions on May 11, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.45; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.45; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.45; and on May 12, 2022: (a) SAI acquired 6,616 shares at $5.40; (b) SAF acquired 1,245 shares at $5.40; and (c) SVP VII acquired 2,139 shares at $5.40.

F6 · 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: 0001104659-22-060300 · tm2215529-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 637,865

F3 · kind: This Form 4 reports the following acquisitions on May 11, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.45; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.45; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.45; and on May 12, 2022: (a) SAI acquired 6,616 shares at $5.40; (b) SAF acquired 1,245 shares at $5.40; and (c) SVP VII acquired 2,139 shares at $5.40.

F5 · 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: 0001104659-22-060300 · tm2215529-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,916,192

F3 · kind: This Form 4 reports the following acquisitions on May 11, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.45; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.45; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.45; and on May 12, 2022: (a) SAI acquired 6,616 shares at $5.40; (b) SAF acquired 1,245 shares at $5.40; and (c) SVP VII acquired 2,139 shares at $5.40.

F4 · ownership.nature: 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.

SEC source: 0001104659-22-060300 · tm2215529-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 916,026

F3 · kind: This Form 4 reports the following acquisitions on May 11, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.45; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.45; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.45; and on May 12, 2022: (a) SAI acquired 6,616 shares at $5.40; (b) SAF acquired 1,245 shares at $5.40; and (c) SVP VII acquired 2,139 shares at $5.40.

F6 · 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: 0001104659-22-060300 · tm2215529-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 636,620

F3 · kind: This Form 4 reports the following acquisitions on May 11, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.45; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.45; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.45; and on May 12, 2022: (a) SAI acquired 6,616 shares at $5.40; (b) SAF acquired 1,245 shares at $5.40; and (c) SVP VII acquired 2,139 shares at $5.40.

F5 · 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: 0001104659-22-060300 · tm2215529-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,909,576

F3 · kind: This Form 4 reports the following acquisitions on May 11, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,616 shares at $5.45; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,245 shares at $5.45; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,139 shares at $5.45; and on May 12, 2022: (a) SAI acquired 6,616 shares at $5.40; (b) SAF acquired 1,245 shares at $5.40; and (c) SVP VII acquired 2,139 shares at $5.40.

F4 · ownership.nature: 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.

SEC source: 0001127602-22-013188 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 90,816

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 20,000 shares of restricted stock granted on February 26, 2021 and 32,754 shares of restricted stock granted on December 3, 2021.

SEC source: 0001127602-22-013190 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,920,059

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 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-012289 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,919,694

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 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-012288 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 90,553

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 20,000 shares of restricted stock granted on February 26, 2021 and 32,754 shares of restricted stock granted on December 3, 2021.

SEC source: 0001127602-22-011218 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,919,311

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 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-011215 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 90,277

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 20,000 shares of restricted stock granted on February 26, 2021 and 32,754 shares of restricted stock granted on December 3, 2021.

SEC source: 0001104659-22-041713 · tm2211288-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 635,375

F3 · kind: This Form 4 reports the following acquisitions on March 30, 2022: (a) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 8,727 shares at $5.50; (b) Stilwell Activist Investments, L.P. ("SAI") acquired 1,273 shares at $5.50; and on March 31, 2022: (a) SVP VII acquired 5,368 shares at $5.50; (b) SAI acquired 16,427 shares at $5.50; and (c) Stilwell Activist Fund, L.P. ("SAF") acquired 3,205 shares at $5.50.

F6 · 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: 0001104659-22-041713 · tm2211288-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,902,960

F3 · kind: This Form 4 reports the following acquisitions on March 30, 2022: (a) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 8,727 shares at $5.50; (b) Stilwell Activist Investments, L.P. ("SAI") acquired 1,273 shares at $5.50; and on March 31, 2022: (a) SVP VII acquired 5,368 shares at $5.50; (b) SAI acquired 16,427 shares at $5.50; and (c) Stilwell Activist Fund, L.P. ("SAF") acquired 3,205 shares at $5.50.

F5 · ownership.nature: 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.

SEC source: 0001104659-22-041713 · tm2211288-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 913,887

F3 · kind: This Form 4 reports the following acquisitions on March 30, 2022: (a) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 8,727 shares at $5.50; (b) Stilwell Activist Investments, L.P. ("SAI") acquired 1,273 shares at $5.50; and on March 31, 2022: (a) SVP VII acquired 5,368 shares at $5.50; (b) SAI acquired 16,427 shares at $5.50; and (c) Stilwell Activist Fund, L.P. ("SAF") acquired 3,205 shares at $5.50.

F4 · 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: 0001104659-22-041713 · tm2211288-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,886,533

F3 · kind: This Form 4 reports the following acquisitions on March 30, 2022: (a) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 8,727 shares at $5.50; (b) Stilwell Activist Investments, L.P. ("SAI") acquired 1,273 shares at $5.50; and on March 31, 2022: (a) SVP VII acquired 5,368 shares at $5.50; (b) SAI acquired 16,427 shares at $5.50; and (c) Stilwell Activist Fund, L.P. ("SAF") acquired 3,205 shares at $5.50.

F5 · ownership.nature: 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.

SEC source: 0001104659-22-041713 · tm2211288-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 908,519

F3 · kind: This Form 4 reports the following acquisitions on March 30, 2022: (a) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 8,727 shares at $5.50; (b) Stilwell Activist Investments, L.P. ("SAI") acquired 1,273 shares at $5.50; and on March 31, 2022: (a) SVP VII acquired 5,368 shares at $5.50; (b) SAI acquired 16,427 shares at $5.50; and (c) Stilwell Activist Fund, L.P. ("SAF") acquired 3,205 shares at $5.50.

F4 · 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: 0001104659-22-040126 · tm2210779-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 899,792

F3 · kind: This Form 4 reports the following acquisitions on March 28, 2022: Stilwell Value Partners VII, L.P. ("SVP VII") acquired 10,000 shares at $5.50; and on March 29, 2022: SVP VII acquired 2,984 shares at $5.48.

F4 · 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: 0001104659-22-040126 · tm2210779-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 896,808

F3 · kind: This Form 4 reports the following acquisitions on March 28, 2022: Stilwell Value Partners VII, L.P. ("SVP VII") acquired 10,000 shares at $5.50; and on March 29, 2022: SVP VII acquired 2,984 shares at $5.48.

F4 · 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: 0001104659-22-038719 · tm2210614-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 632,170

F3 · kind: This Form 4 reports the following acquisitions on March 24, 2022: Stilwell Value Partners VII, L.P. ("SVP VII") acquired 10,000 shares at $5.50; and on March 25, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,495 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,505 shares at $5.50 USD per share.

F6 · 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: 0001104659-22-038719 · tm2210614-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,885,260

F3 · kind: This Form 4 reports the following acquisitions on March 24, 2022: Stilwell Value Partners VII, L.P. ("SVP VII") acquired 10,000 shares at $5.50; and on March 25, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,495 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,505 shares at $5.50 USD per share.

F5 · ownership.nature: 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.

SEC source: 0001104659-22-038719 · tm2210614-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 886,808

F3 · kind: This Form 4 reports the following acquisitions on March 24, 2022: Stilwell Value Partners VII, L.P. ("SVP VII") acquired 10,000 shares at $5.50; and on March 25, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,495 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,505 shares at $5.50 USD per share.

F4 · 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: 0001104659-22-037481 · tm2210388-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 630,665

F3 · kind: This Form 4 reports the following acquisitions on March 22, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,215 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,785 shares at $5.50 USD per share; and on March 23, 2022: (a) SAI acquired 8,495 shares at $5.50 USD per share; and (b) SAF acquired 1,505 shares at $5.50 USD per share.

F5 · 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: 0001104659-22-037481 · tm2210388-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,876,765

F3 · kind: This Form 4 reports the following acquisitions on March 22, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,215 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,785 shares at $5.50 USD per share; and on March 23, 2022: (a) SAI acquired 8,495 shares at $5.50 USD per share; and (b) SAF acquired 1,505 shares at $5.50 USD per share.

F4 · ownership.nature: 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.

SEC source: 0001104659-22-037481 · tm2210388-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 629,160

F3 · kind: This Form 4 reports the following acquisitions on March 22, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,215 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,785 shares at $5.50 USD per share; and on March 23, 2022: (a) SAI acquired 8,495 shares at $5.50 USD per share; and (b) SAF acquired 1,505 shares at $5.50 USD per share.

F5 · 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: 0001104659-22-037481 · tm2210388-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,868,270

F3 · kind: This Form 4 reports the following acquisitions on March 22, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,215 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,785 shares at $5.50 USD per share; and on March 23, 2022: (a) SAI acquired 8,495 shares at $5.50 USD per share; and (b) SAF acquired 1,505 shares at $5.50 USD per share.

F4 · ownership.nature: 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.

SEC source: 0001104659-22-036545 · tm2210131-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,860,055

F3 · kind: This Form 4 reports the following acquisitions on March 18, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,495 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,505 shares at $5.50 USD per share; and on March 21, 2022: SAI acquired 2,795 shares at $5.50 USD per share.

F4 · ownership.nature: 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.

SEC source: 0001104659-22-036545 · tm2210131-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 627,375

F3 · kind: This Form 4 reports the following acquisitions on March 18, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,495 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,505 shares at $5.50 USD per share; and on March 21, 2022: SAI acquired 2,795 shares at $5.50 USD per share.

F5 · 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: 0001104659-22-036545 · tm2210131-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,857,260

F3 · kind: This Form 4 reports the following acquisitions on March 18, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,495 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,505 shares at $5.50 USD per share; and on March 21, 2022: SAI acquired 2,795 shares at $5.50 USD per share.

F4 · ownership.nature: 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.

SEC source: 0001104659-22-035539 · tm229754-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 625,870

F3 · kind: This Form 4 reports the following acquisitions on March 16, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,495 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,505 shares at $5.50 USD per share; and on March 17, 2022: (a) SAI acquired 8,495 shares at $5.50 USD per share; and (b) SAF acquired 1,505 shares at $5.50 USD per share.

F5 · 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: 0001104659-22-035539 · tm229754-1_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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,848,765

F3 · kind: This Form 4 reports the following acquisitions on March 16, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 8,495 shares at $5.50; and (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,505 shares at $5.50 USD per share; and on March 17, 2022: (a) SAI acquired 8,495 shares at $5.50 USD per share; and (b) SAF acquired 1,505 shares at $5.50 USD per share.

F4 · ownership.nature: 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.

SEC source: 0001127602-22-009476 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 90,011

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 20,000 shares of restricted stock granted on February 26, 2021 and 32,754 shares of restricted stock granted on December 3, 2021.

SEC source: 0001127602-22-009477 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,918,942

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 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.