KWY

SEC source: 0001127602-22-025736 · 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: 1,880,547

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: 0001127602-22-024589 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 93,695

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: 0001127602-22-024592 · 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: 1,880,257

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: 0001127602-22-023941 · 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: 1,879,957

F1 · kind: 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: 0001127602-22-023940 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 93,479

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: 0001127602-22-023539 · 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: 1,879,609

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: 0001127602-22-023538 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 93,229

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: 0001127602-22-022668 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 93,018

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: 0001127602-22-022667 · 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: 1,879,316

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: 0001127602-22-022146 · 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: 1,879,014

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 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: 0001127602-22-021814 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 92,801

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: 0001127602-22-021813 · 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: 1,922,820

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

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-021065 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 92,591

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: 0001127602-22-021064 · 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: 1,922,527

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

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-020469 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 92,392

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: 0001127602-22-020471 · 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: 1,922,251

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

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-019419 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 92,156

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: 0001127602-22-019418 · 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: 1,921,923

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

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-018494 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 91,910

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: 0001127602-22-018492 · 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: 1,921,580

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

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-22-018491 · form4.xml · nonDerivative · entry 2

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,576,694

SEC source: 0001127602-22-018487 · form4.xml · nonDerivative · entry 2

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 2,611,444

F2 · balance_after: Terence Michael Kavanagh directly owns shares of common stock (1,750 shares) and indirectly through Retirement Savings Plan (26,875 shares), E.J.K. Holdings, Inc. (6,000 shares), in trust for W. Aikman (125 shares) and Oakmont Capital Inc. (2,576,694 shares).

SEC source: 0001127602-22-018489 · form4.xml · nonDerivative · entry 2

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc

Disclosed balance after: 2,624,444

F2 · balance_after: Gregory Paul Hannon, indirectly owns shares of common stock through Retirement Savings Plan (22,500 shares), 1272562 Ontario Inc. (3,000 shares), Oakmont Capital Inc. (2,576,694) his spouse (13,750 shares), trusts for his children (4,500 shares), and Gilter Inc. (4,000 shares).

SEC source: 0001127602-22-018491 · form4.xml · nonDerivative · entry 1

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,547,708

SEC source: 0001127602-22-018487 · form4.xml · nonDerivative · entry 1

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 2,582,458

F1 · balance_after: Terence Michael Kavanagh directly owns shares of common stock (1,750 shares) and indirectly through Retirement Savings Plan (26,875 shares), E.J.K. Holdings, Inc. (6,000 shares), in trust for W. Aikman (125 shares) and Oakmont Capital Inc. (2,547,708 shares).

SEC source: 0001127602-22-018489 · form4.xml · nonDerivative · entry 1

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc

Disclosed balance after: 2,595,458

F1 · balance_after: Gregory Paul Hannon, indirectly owns shares of common stock through Retirement Savings Plan (22,500 shares), 1272562 Ontario Inc. (3,000 shares), Oakmont Capital Inc. (2,547,708 shares) his spouse (13,750 shares), trusts for his children (4,500 shares), and Gilter Inc. (4,000 shares).

SEC source: 0001127602-22-018198 · form4.xml · nonDerivative · entry 2

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,522,708

SEC source: 0001127602-22-018197 · form4.xml · nonDerivative · entry 2

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 2,557,458

F2 · balance_after: Terence Michael Kavanagh directly owns shares of common stock (1,750 shares) and indirectly through Retirement Savings Plan (26,875 shares), E.J.K. Holdings, Inc. (6,000 shares), in trust for W. Aikman (125 shares) and Oakmont Capital Inc. (2,522,708 shares).

SEC source: 0001127602-22-018195 · form4.xml · nonDerivative · entry 2

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc

Disclosed balance after: 2,570,458

F2 · balance_after: Gregory Paul Hannon, indirectly owns shares of common stock through Retirement Savings Plan (22,500 shares), 1272562 Ontario Inc. (3,000 shares), Oakmont Capital Inc. (2,522,708 shares) his spouse (13,750 shares), trusts for his children (4,500 shares), and Gilter Inc. (4,000 shares).

SEC source: 0001127602-22-018198 · form4.xml · nonDerivative · entry 1

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,518,850

SEC source: 0001127602-22-018197 · form4.xml · nonDerivative · entry 1

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 2,553,600

F1 · balance_after: Terence Michael Kavanagh directly owns shares of common stock (1,750 shares) and indirectly through Retirement Savings Plan (26,875 shares), E.J.K. Holdings, Inc. (6,000 shares), in trust for W. Aikman (125 shares) and Oakmont Capital Inc. (2,518,850 shares).

SEC source: 0001127602-22-018195 · form4.xml · nonDerivative · entry 1

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc

Disclosed balance after: 2,566,600

F1 · balance_after: Gregory Paul Hannon, indirectly owns shares of common stock through Retirement Savings Plan (22,500 shares), 1272562 Ontario Inc. (3,000 shares), Oakmont Capital Inc. (2,518,850 shares) his spouse (13,750 shares), trusts for his children (4,500 shares), and Gilter Inc. (4,000 shares).

SEC source: 0001127602-22-018130 · form4.xml · nonDerivative · entry 2

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,512,396

SEC source: 0001127602-22-018128 · form4.xml · nonDerivative · entry 2

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc

Disclosed balance after: 2,560,146

F2 · balance_after: Gregory Paul Hannon, indirectly owns shares of common stock through Retirement Savings Plan (22,500 shares), 1272562 Ontario Inc. (3,000 shares), Oakmont Capital Inc. (2,512,396 shares) his spouse (13,750 shares), trusts for his children (4,500 shares), and Gilter Inc. (4,000 shares).

SEC source: 0001127602-22-018125 · form4.xml · nonDerivative · entry 2

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 2,547,146

F2 · balance_after: Terence Michael Kavanagh directly owns shares of common stock (1,750 shares) and indirectly through Retirement Savings Plan (26,875 shares), E.J.K. Holdings, Inc. (6,000 shares), in trust for W. Aikman (125 shares) and Oakmont Capital Inc. (2,512,396 shares).

SEC source: 0001104659-22-074738 · tm2219500-1_4seq1.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

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

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

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 5,048,333

F3 · kind: This Form 4 reports the following acquisition on June 23, 2022: Stilwell Activist Investments, L.P. ("SAI") acquired 500 shares at $5.3374.

F4 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

SEC source: 0001104659-22-073887 · tm2219309-1_4seq1.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: 5,047,833

F3 · kind: This Form 4 reports the following acquisitions on June 21, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 3,351 shares at $5.35; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 588 shares at $5.35; (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,061 shares at $5.35; (d) SAI acquired 6,701 shares at $5.30; (e) SAF acquired 1,177 shares at $5.30; and (f) SVP VII acquired 2,122 shares at $5.30; and on June 22, 2022: (a) SAI acquired 308 shares at $5.15.

F4 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

SEC source: 0001127602-22-018130 · form4.xml · nonDerivative · entry 1

OAKMONT CAPITAL INC · CIK 0001071674 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,477,736

SEC source: 0001127602-22-018128 · form4.xml · nonDerivative · entry 1

Hannon Gregory Paul · CIK 0001538186 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc

Disclosed balance after: 2,525,486

F1 · balance_after: Gregory Paul Hannon, indirectly owns shares of common stock through Retirement Savings Plan (22,500 shares), 1272562 Ontario Inc. (3,000 shares), Oakmont Capital Inc. (2,477,736 shares) his spouse (13,750 shares), trusts for his children (4,500 shares), and Gilter Inc. (4,000 shares).

SEC source: 0001127602-22-018125 · form4.xml · nonDerivative · entry 1

Kavanagh Terence Michael · CIK 0001538185 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · By Oakmont Capital Inc.

Disclosed balance after: 2,512,486

F1 · balance_after: Terence Michael Kavanagh directly owns shares of common stock (1,750 shares) and indirectly through Retirement Savings Plan (26,875 shares), E.J.K. Holdings, Inc. (6,000 shares), in trust for W. Aikman (125 shares) and Oakmont Capital Inc. (2,477,736 shares).

SEC source: 0001104659-22-073887 · tm2219309-1_4seq1.xml · nonDerivative · entry 8

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

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

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

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 960,559

F3 · kind: This Form 4 reports the following acquisitions on June 21, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 3,351 shares at $5.35; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 588 shares at $5.35; (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,061 shares at $5.35; (d) SAI acquired 6,701 shares at $5.30; (e) SAF acquired 1,177 shares at $5.30; and (f) SVP VII acquired 2,122 shares at $5.30; and on June 22, 2022: (a) SAI acquired 308 shares at $5.15.

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

SEC source: 0001104659-22-073887 · tm2219309-1_4seq1.xml · nonDerivative · entry 7

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

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

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

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 665,138

F3 · kind: This Form 4 reports the following acquisitions on June 21, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 3,351 shares at $5.35; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 588 shares at $5.35; (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,061 shares at $5.35; (d) SAI acquired 6,701 shares at $5.30; (e) SAF acquired 1,177 shares at $5.30; and (f) SVP VII acquired 2,122 shares at $5.30; and on June 22, 2022: (a) SAI acquired 308 shares at $5.15.

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

SEC source: 0001104659-22-073887 · tm2219309-1_4seq1.xml · nonDerivative · entry 6

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

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

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

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 5,047,525

F3 · kind: This Form 4 reports the following acquisitions on June 21, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 3,351 shares at $5.35; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 588 shares at $5.35; (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,061 shares at $5.35; (d) SAI acquired 6,701 shares at $5.30; (e) SAF acquired 1,177 shares at $5.30; and (f) SVP VII acquired 2,122 shares at $5.30; and on June 22, 2022: (a) SAI acquired 308 shares at $5.15.

F4 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

SEC source: 0001104659-22-073887 · tm2219309-1_4seq1.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

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

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

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 958,437

F3 · kind: This Form 4 reports the following acquisitions on June 21, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 3,351 shares at $5.35; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 588 shares at $5.35; (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,061 shares at $5.35; (d) SAI acquired 6,701 shares at $5.30; (e) SAF acquired 1,177 shares at $5.30; and (f) SVP VII acquired 2,122 shares at $5.30; and on June 22, 2022: (a) SAI acquired 308 shares at $5.15.

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

SEC source: 0001104659-22-073887 · tm2219309-1_4seq1.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

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

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

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 663,961

F3 · kind: This Form 4 reports the following acquisitions on June 21, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 3,351 shares at $5.35; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 588 shares at $5.35; (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,061 shares at $5.35; (d) SAI acquired 6,701 shares at $5.30; (e) SAF acquired 1,177 shares at $5.30; and (f) SVP VII acquired 2,122 shares at $5.30; and on June 22, 2022: (a) SAI acquired 308 shares at $5.15.

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

SEC source: 0001104659-22-073887 · tm2219309-1_4seq1.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

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

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

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 5,040,824

F3 · kind: This Form 4 reports the following acquisitions on June 21, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 3,351 shares at $5.35; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 588 shares at $5.35; (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,061 shares at $5.35; (d) SAI acquired 6,701 shares at $5.30; (e) SAF acquired 1,177 shares at $5.30; and (f) SVP VII acquired 2,122 shares at $5.30; and on June 22, 2022: (a) SAI acquired 308 shares at $5.15.

F4 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

SEC source: 0001104659-22-072943 · tm2218997-1_4seq1.xml · nonDerivative · entry 6

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

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

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

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 663,373

F3 · kind: This Form 4 reports the following acquisitions on June 16, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 5,772 shares at $5.30; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,086 shares at $5.30; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,866 shares at $5.30; and on June 17, 2022: SAF acquired 1,056 shares at $5.30.

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

SEC source: 0001127602-22-017749 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 91,649

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: 0001127602-22-017753 · 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: 1,921,217

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

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001104659-22-072943 · tm2218997-1_4seq1.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

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

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

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 957,376

F3 · kind: This Form 4 reports the following acquisitions on June 16, 2022: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 5,772 shares at $5.30; (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,086 shares at $5.30; and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,866 shares at $5.30; and on June 17, 2022: SAF acquired 1,056 shares at $5.30.

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