KWY

SEC source: 0001072627-26-000055 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136,672

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 Corporation 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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000056 · 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: 1,427,430

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 Corporation 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 300,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001104659-26-112426 · tm2626738-1_4seq1.xml · nonDerivative · entry 2

Horowitz Joshua · CIK 0001612424 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · by Palm Global Small Cap Master Fund LP

Disclosed balance after: 384,678

F2 · ownership.nature: Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP ("Palm Global"), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

SEC source: 0001104659-26-112426 · tm2626738-1_4seq1.xml · nonDerivative · entry 1

Horowitz Joshua · CIK 0001612424 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · by Palm Global Small Cap Master Fund LP

Disclosed balance after: 383,820

F3 · price: The price reported represents a weighted average price. These shares were purchased in multiple transactions at prices ranging from $9.255 to $9.28 per share. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price.

F2 · ownership.nature: Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP ("Palm Global"), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

SEC source: 0001072627-26-000054 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136,503

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 Corporation 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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000053 · 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: 1,427,161

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 Corporation 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 300,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-26-000052 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136,344

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 Corporation 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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000051 · 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: 1,426,907

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 Corporation 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 300,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001104659-26-099299 · tm2623741-1_4seq1.xml · nonDerivative · entry 3

Horowitz Joshua · CIK 0001612424 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · by Palm Global Small Cap Master Fund LP

Disclosed balance after: 381,103

F2 · ownership.nature: Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP ("Palm Global"), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

SEC source: 0001104659-26-099299 · tm2623741-1_4seq1.xml · nonDerivative · entry 2

Horowitz Joshua · CIK 0001612424 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · by Palm Global Small Cap Master Fund LP

Disclosed balance after: 380,334

F3 · price: The price reported represents a weighted average price. These shares were purchased in multiple transactions at prices ranging from $9.82 to $9.86 per share. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price.

F2 · ownership.nature: Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP ("Palm Global"), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

SEC source: 0001104659-26-099299 · tm2623741-1_4seq1.xml · nonDerivative · entry 1

Horowitz Joshua · CIK 0001612424 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · by Palm Global Small Cap Master Fund LP

Disclosed balance after: 373,300

F2 · ownership.nature: Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP ("Palm Global"), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

SEC source: 0001072627-26-000050 · 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: 1,426,668

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 Corporation 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 300,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-26-000049 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136,195

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 Corporation 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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001104659-26-097865 · tm2623411d1_4seq1.xml · nonDerivative · entry 4

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

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

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

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

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

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

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 330,718

F2 · kind: This Form 4 reports the following sales on August 13, 2026: Stilwell Associates, L.P. ("Associates") sold 32,982 shares at $10.00; Stilwell Activist Investments, L.P. ("SAI") sold 26,168 shares at $10.00; and Stilwell Value Partners VII, L.P. ("SVP VII") sold 40,850 shares at $10.00.

F5 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

SEC source: 0001104659-26-097865 · tm2623411d1_4seq1.xml · nonDerivative · entry 3

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

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

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

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

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

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

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 2,228,803

F2 · kind: This Form 4 reports the following sales on August 13, 2026: Stilwell Associates, L.P. ("Associates") sold 32,982 shares at $10.00; Stilwell Activist Investments, L.P. ("SAI") sold 26,168 shares at $10.00; and Stilwell Value Partners VII, L.P. ("SVP VII") sold 40,850 shares at $10.00.

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: 0001104659-26-097865 · tm2623411d1_4seq1.xml · nonDerivative · entry 2

Stilwell Joseph · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

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

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

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

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

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

10b5-1 filing: No plan indicated

Ownership: Indirect · See footnote

Disclosed balance after: 267,018

F2 · kind: This Form 4 reports the following sales on August 13, 2026: Stilwell Associates, L.P. ("Associates") sold 32,982 shares at $10.00; Stilwell Activist Investments, L.P. ("SAI") sold 26,168 shares at $10.00; and Stilwell Value Partners VII, L.P. ("SVP VII") sold 40,850 shares at $10.00.

F3 · ownership.nature: These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

SEC source: 0001072627-26-000047 · 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: 1,426,414

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 Corporation 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 300,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-26-000048 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136,037

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 Corporation 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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000046 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,863

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 Corporation 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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000045 · 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: 1,426,136

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 Corporation 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 300,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-26-000044 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,702

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 Corporation 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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000043 · 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: 1,425,880

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 Corporation 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 300,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-26-000041 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,553

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 Corporation 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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000040 · 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: 1,455,874

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 Corporation The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

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

SEC source: 0001072627-26-000042 · 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: 1,425,641

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 300,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001072627-26-000039 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,403

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 Corporation 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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000038 · 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: 1,455,634

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 Corporation The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

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

SEC source: 0001104659-26-069022 · tm2616582-1_4seq1.xml · nonDerivative · entry 2

Horowitz Joshua · CIK 0001612424 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · by Palm Global Small Cap Master Fund LP

Disclosed balance after: 372,000

F3 · price: The price reported represents a weighted average price. These shares were purchased in multiple transactions at prices ranging from $9.80 to $9.95 per share. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price.

F2 · ownership.nature: Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP ("Palm Global"), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

SEC source: 0001104659-26-069022 · tm2616582-1_4seq1.xml · nonDerivative · entry 1

Horowitz Joshua · CIK 0001612424 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · by Palm Global Small Cap Master Fund LP

Disclosed balance after: 368,200

F2 · ownership.nature: Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP ("Palm Global"), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

SEC source: 0001072627-26-000037 · 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: 1,455,384

F1 · shares: Charitable gift.

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

SEC source: 0001072627-26-000036 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust-MPF

Disclosed balance after: 29,100

SEC source: 0001072627-26-000035 · form4.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust-LTF

Disclosed balance after: 29,100

SEC source: 0001072627-26-000035 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust-GEF

Disclosed balance after: 29,100

SEC source: 0001072627-26-000034 · form4.xml · derivative · entry 5

Patinkin Adam Jonathan · CIK 0002063594 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 200,000

Underlying: Common Stock · 200,000 shares

Expires 2036-05-18

F4 · derivative.exercise_price: The option consists of tranches with different exercise prices. An aggregate of 200,000 options have an exercise price of $20 per share, of which 100,000 vested on the grant date and 100,000 will vest on the first anniversary of the grant date. The remaining 200,000 options have an exercise price of $30 per share, with 100,000 vesting on the second anniversary of the grant date and 100,000 vesting on the third anniversary of the grant date.

F5 · derivative.expiration_date: Represents a 10-year stock option to purchase an aggregate of 400,000 shares of common stock. The option vests as follows: (i) 100,000 shares vested on the grant date at an exercise price of $20 per share; (ii) 100,000 shares will vest on the first anniversary of the grant date at an exercise price of $20 per share; (iii) 100,000 shares will vest on the second anniversary of the grant date at an exercise price of $30 per share; and (iv) 100,000 shares will vest on the third anniversary of the grant date at an exercise price of $30 per share. Vesting is subject to the reporting person's continued service through each applicable vesting date.

SEC source: 0001072627-26-000034 · form4.xml · derivative · entry 4

Patinkin Adam Jonathan · CIK 0002063594 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 200,000

Underlying: Common Stock · 200,000 shares

Expires 2036-05-18

F4 · derivative.exercise_price: The option consists of tranches with different exercise prices. An aggregate of 200,000 options have an exercise price of $20 per share, of which 100,000 vested on the grant date and 100,000 will vest on the first anniversary of the grant date. The remaining 200,000 options have an exercise price of $30 per share, with 100,000 vesting on the second anniversary of the grant date and 100,000 vesting on the third anniversary of the grant date.

F5 · derivative.expiration_date: Represents a 10-year stock option to purchase an aggregate of 400,000 shares of common stock. The option vests as follows: (i) 100,000 shares vested on the grant date at an exercise price of $20 per share; (ii) 100,000 shares will vest on the first anniversary of the grant date at an exercise price of $20 per share; (iii) 100,000 shares will vest on the second anniversary of the grant date at an exercise price of $30 per share; and (iv) 100,000 shares will vest on the third anniversary of the grant date at an exercise price of $30 per share. Vesting is subject to the reporting person's continued service through each applicable vesting date.

SEC source: 0001072627-26-000032 · 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: 1,461,641

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

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

SEC source: 0001072627-26-000031 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,247

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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000027 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 135,103

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 6,909 shares of restricted stock granted on December 4, 2024, and 14,568 shares of restricted stock granted on March 17, 2026.

SEC source: 0001072627-26-000026 · 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: 1,461,411

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

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

SEC source: 0001072627-26-000025 · 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: 1,461,182

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

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

SEC source: 0001072627-26-000020 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 120,260

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 7,102 shares of restricted stock granted on March 26, 2024 and 13,818 shares of restricted stock granted on December 4, 2024.

SEC source: 0001072627-26-000019 · 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: 1,460,971

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

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

SEC source: 0001072627-26-000023 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 134,675

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, 2026.

F2 · balance_after: Includes 7,102 shares of restricted stock granted on March 26, 2024 and 13,818 shares of restricted stock granted on December 4, 2024.

SEC source: 0001072627-26-000018 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,460,727

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

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

SEC source: 0001072627-26-000017 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 120,107

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 7,102 shares of restricted stock granted on March 26, 2024 and 13,818 shares of restricted stock granted on December 4, 2024.

SEC source: 0001072627-26-000014 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 119,961

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 7,102 shares of restricted stock granted on March 26, 2024 and 13,818 shares of restricted stock granted on December 4, 2024.

SEC source: 0001072627-26-000013 · 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: 1,460,493

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

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

SEC source: 0001072627-26-000012 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 119,835

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 7,102 shares of restricted stock granted on March 26, 2024 and 13,818 shares of restricted stock granted on December 4, 2024.

SEC source: 0001072627-26-000011 · 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: 1,460,291

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

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

SEC source: 0001072627-26-000010 · 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: 1,460,086

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

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