KWY

SEC source: 0001127602-23-011401 · form4.xml · nonDerivative · entry 1

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By E.J.K. Holdings, Inc.

Disclosed balance after: 0

SEC source: 0001127602-23-011689 · form4.xml · derivative · entry 2

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 463,394 shares

Expires 2023-09-15

SEC source: 0001127602-23-011689 · form4.xml · nonDerivative · entry 1

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,576,695

SEC source: 0001127602-23-011691 · form4a.xml · derivative · entry 5

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 0

Underlying: Common Stock · 463,394 shares

Expires 2023-09-15

F1 · date: The reporting person is amending the Form 4 originally filed to report this Warrant exercise that also occurred on March 23, 2023.

SEC source: 0001127602-23-011691 · form4a.xml · nonDerivative · entry 1

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Oakmont Capital Inc

Disclosed balance after: 2,576,695

F1 · date: The reporting person is amending the Form 4 originally filed to report this Warrant exercise that also occurred on March 23, 2023.

SEC source: 0001127602-23-011690 · form4a.xml · derivative · entry 3

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 0

Underlying: Common Stock · 463,394 shares

Expires 2023-09-15

F1 · date: The reporting person is amending the Form 4 originally filed to report this Warrant exercise that also occurred on March 23, 2023.

SEC source: 0001127602-23-011690 · form4a.xml · nonDerivative · entry 1

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 2,576,695

F1 · date: The reporting person is amending the Form 4 originally filed to report this Warrant exercise that also occurred on March 23, 2023.

SEC source: 0001127602-23-011198 · form4.xml · derivative · entry 2

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 82,143.75 shares

Expires 2023-03-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded to the next whole share).

F1 · derivative.underlying_shares: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded to the next whole share).

SEC source: 0001127602-23-011198 · form4.xml · nonDerivative · entry 1

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,113,301

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded to the next whole share).

F2 · balance_after: The reporting person's previous Form 4 filings incorrectly listed the number of securities beneficially owned due to an administrative error which has been corrected in calculating the number of securities beneficially owned following the transaction reported herein.

SEC source: 0001127602-23-011201 · form4.xml · derivative · entry 9

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 0

Underlying: Common Stock · 82,143.75 shares

Expires 2023-03-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded to the next whole share).

F1 · derivative.underlying_shares: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded to the next whole share).

SEC source: 0001127602-23-011201 · form4.xml · nonDerivative · entry 1

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Oakmont Capital Inc

Disclosed balance after: 2,113,301

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded to the next whole share).

F2 · balance_after: The reporting person's previous Form 4 filings incorrectly listed the number of securities beneficially owned due to an administrative error which has been corrected in calculating the number of securities beneficially owned following the transaction reported herein.

SEC source: 0001127602-23-011200 · form4.xml · derivative · entry 6

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 0

Underlying: Common Stock · 82,143.75 shares

Expires 2023-03-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded to the next whole share).

F1 · derivative.underlying_shares: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded to the next whole share).

SEC source: 0001127602-23-011200 · form4.xml · nonDerivative · entry 1

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 2,113,301

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded to the next whole share).

F2 · balance_after: The reporting person's previous Form 4 filings incorrectly listed the number of securities beneficially owned due to an administrative error which has been corrected in calculating the number of securities beneficially owned following the transaction reported herein.

SEC source: 0001127602-23-011195 · form4.xml · derivative · entry 4

LEVINE DOUGLAS · CIK 0001164694 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 166,187.5 shares

Expires 2023-03-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded down).

F1 · derivative.underlying_shares: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded down).

SEC source: 0001127602-23-011195 · form4.xml · nonDerivative · entry 1

LEVINE DOUGLAS · CIK 0001164694 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,157,671

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded down).

SEC source: 0001127602-23-010874 · 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: 1,882,583

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 600,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-010873 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 106,810

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 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001104659-23-032756 · tm239688d1_4.xml · nonDerivative · entry 9

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: 919,656

F2 · kind: This Form 4 reports the following sales: on March 13, 2023: (a) Stilwell Activist Investments, L.P. ("SAI") sold 43,139 shares at $9.0293; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,684 shares at $9.0293; (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 8,151 shares at $9.0293; and Stilwell Associates LP ("Associates") sold 8,026 shares at $9.0293; and on March 14, 2023: (a) SAI sold 63,519 shares at $9.0013; (b) SAF sold 8,881 shares at $9.0013; (c) SVP VII sold 11,740 shares at $9.0013; and Associates sold 11,560 shares at $9.0013.

F6 · ownership.nature: These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

SEC source: 0001104659-23-032756 · tm239688d1_4.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: 934,018

F2 · kind: This Form 4 reports the following sales: on March 13, 2023: (a) Stilwell Activist Investments, L.P. ("SAI") sold 43,139 shares at $9.0293; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,684 shares at $9.0293; (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 8,151 shares at $9.0293; and Stilwell Associates LP ("Associates") sold 8,026 shares at $9.0293; and on March 14, 2023: (a) SAI sold 63,519 shares at $9.0013; (b) SAF sold 8,881 shares at $9.0013; (c) SVP VII sold 11,740 shares at $9.0013; and Associates sold 11,560 shares at $9.0013.

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 Stilwell Value LLC ("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: 0001104659-23-032756 · tm239688d1_4.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: 650,573

F2 · kind: This Form 4 reports the following sales: on March 13, 2023: (a) Stilwell Activist Investments, L.P. ("SAI") sold 43,139 shares at $9.0293; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,684 shares at $9.0293; (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 8,151 shares at $9.0293; and Stilwell Associates LP ("Associates") sold 8,026 shares at $9.0293; and on March 14, 2023: (a) SAI sold 63,519 shares at $9.0013; (b) SAF sold 8,881 shares at $9.0013; (c) SVP VII sold 11,740 shares at $9.0013; and Associates sold 11,560 shares at $9.0013.

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: 0001104659-23-032756 · tm239688d1_4.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: 4,941,675

F2 · kind: This Form 4 reports the following sales: on March 13, 2023: (a) Stilwell Activist Investments, L.P. ("SAI") sold 43,139 shares at $9.0293; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,684 shares at $9.0293; (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 8,151 shares at $9.0293; and Stilwell Associates LP ("Associates") sold 8,026 shares at $9.0293; and on March 14, 2023: (a) SAI sold 63,519 shares at $9.0013; (b) SAF sold 8,881 shares at $9.0013; (c) SVP VII sold 11,740 shares at $9.0013; and Associates sold 11,560 shares at $9.0013.

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 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: 0001104659-23-032756 · tm239688d1_4.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: 931,216

F2 · kind: This Form 4 reports the following sales: on March 13, 2023: (a) Stilwell Activist Investments, L.P. ("SAI") sold 43,139 shares at $9.0293; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,684 shares at $9.0293; (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 8,151 shares at $9.0293; and Stilwell Associates LP ("Associates") sold 8,026 shares at $9.0293; and on March 14, 2023: (a) SAI sold 63,519 shares at $9.0013; (b) SAF sold 8,881 shares at $9.0013; (c) SVP VII sold 11,740 shares at $9.0013; and Associates sold 11,560 shares at $9.0013.

F6 · ownership.nature: These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

SEC source: 0001104659-23-032756 · tm239688d1_4.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: 945,758

F2 · kind: This Form 4 reports the following sales: on March 13, 2023: (a) Stilwell Activist Investments, L.P. ("SAI") sold 43,139 shares at $9.0293; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,684 shares at $9.0293; (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 8,151 shares at $9.0293; and Stilwell Associates LP ("Associates") sold 8,026 shares at $9.0293; and on March 14, 2023: (a) SAI sold 63,519 shares at $9.0013; (b) SAF sold 8,881 shares at $9.0013; (c) SVP VII sold 11,740 shares at $9.0013; and Associates sold 11,560 shares at $9.0013.

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 Stilwell Value LLC ("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: 0001104659-23-032756 · tm239688d1_4.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: 659,454

F2 · kind: This Form 4 reports the following sales: on March 13, 2023: (a) Stilwell Activist Investments, L.P. ("SAI") sold 43,139 shares at $9.0293; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,684 shares at $9.0293; (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 8,151 shares at $9.0293; and Stilwell Associates LP ("Associates") sold 8,026 shares at $9.0293; and on March 14, 2023: (a) SAI sold 63,519 shares at $9.0013; (b) SAF sold 8,881 shares at $9.0013; (c) SVP VII sold 11,740 shares at $9.0013; and Associates sold 11,560 shares at $9.0013.

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: 0001104659-23-032756 · tm239688d1_4.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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 5,005,194

F2 · kind: This Form 4 reports the following sales: on March 13, 2023: (a) Stilwell Activist Investments, L.P. ("SAI") sold 43,139 shares at $9.0293; (b) Stilwell Activist Fund, L.P. ("SAF") sold 5,684 shares at $9.0293; (c) Stilwell Value Partners VII, L.P. ("SVP VII") sold 8,151 shares at $9.0293; and Stilwell Associates LP ("Associates") sold 8,026 shares at $9.0293; and on March 14, 2023: (a) SAI sold 63,519 shares at $9.0013; (b) SAF sold 8,881 shares at $9.0013; (c) SVP VII sold 11,740 shares at $9.0013; and Associates sold 11,560 shares at $9.0013.

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 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: 0001127602-23-007866 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 106,626

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 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-007863 · 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: 1,882,334

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 600,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-005319 · 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: 1,882,118

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 600,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-005317 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 106,470

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 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-002602 · 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: 1,881,884

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 600,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-002597 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 106,302

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 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-001462 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 106,116

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 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-001461 · 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: 1,881,626

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 600,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-000448 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 105,935

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 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-000445 · 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: 1,881,374

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 600,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001104659-23-000383 · tm231499-1_4.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: 953,909

F2 · kind: This Form 4 reports the following sales: on December 29, 2022 Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,275 shares at $8.023 and on December 30, 2022 SVP VII sold 1,375 shares at $8.00.

F3 · 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 Stilwell Value LLC ("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: 0001104659-23-000383 · tm231499-1_4.xml · derivative · 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: 0

Underlying: Common Stock · 708,347 shares

Expires 2023-09-15

F7 · ownership.nature: Prior to the sale of all Series B Warrants, SAI directly owned 478,582 Series B Warrants, SAF directly owned 48,004 Series B Warrants, Joseph Stilwell directly owned 31,250 Series B Warrants and Associates directly owned 150,511 Series B Warrants. Joseph Stilwell disclaims beneficial ownership of all warrants reported as owned indirectly except to the extent of his pecuniary interest therein.

SEC source: 0001104659-23-000383 · tm231499-1_4.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: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 955,284

F2 · kind: This Form 4 reports the following sales: on December 29, 2022 Stilwell Value Partners VII, L.P. ("SVP VII") sold 5,275 shares at $8.023 and on December 30, 2022 SVP VII sold 1,375 shares at $8.00.

F3 · 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 Stilwell Value LLC ("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: 0001127602-22-027655 · form4.xml · nonDerivative · entry 2

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 105,749

F4 · 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.

F3 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021.

SEC source: 0001127602-22-027654 · 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: 1,881,116

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 600,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-027655 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 105,544

F1 · shares: Restricted stock award granted pursuant to the Kingsway Financial Services Inc. 2020 Equity Incentive Plan that vests ratably over three years commencing on December 1, 2023

F2 · price: The number of shares represented by this award was determined by dividing the dollar value of the award granted to the Reporting Person by $7.168 (the volume-weighted average of the closing sale prices of the Issuer's common stock on the NYSE?for each of the thirty (30) trading days immediately prior to the grant date).

F3 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021.

SEC source: 0001127602-22-027180 · form4.xml · nonDerivative · entry 1

Frischer Charles L · CIK 0001402258 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,584,278

SEC source: 0001127602-22-027074 · form4.xml · nonDerivative · entry 1

Frischer Charles L · CIK 0001402258 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,580,821

SEC source: 0001127602-22-026968 · form4.xml · nonDerivative · entry 2

Frischer Charles L · CIK 0001402258 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,569,098

SEC source: 0001127602-22-026897 · form4.xml · nonDerivative · entry 2

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 80,433

F1 · shares: Reflects shares of the Issuer's common stock surrendered by the Reporting Person to satisfy tax withholding obligations upon the vesting of shares granted under a restricted stock agreement.

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021.

SEC source: 0001127602-22-026968 · form4.xml · nonDerivative · entry 1

Frischer Charles L · CIK 0001402258 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,567,098

SEC source: 0001127602-22-026897 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 85,259

F1 · shares: Reflects shares of the Issuer's common stock surrendered by the Reporting Person to satisfy tax withholding obligations upon the vesting of shares granted under a restricted stock agreement.

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021.

SEC source: 0001127602-22-026570 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 94,108

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: 0001127602-22-026569 · 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: 1,880,831

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 600,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-025737 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 93,903

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.