Hansen Kent A

SEC source: 0001127602-24-028279 · form4.xml · nonDerivative · entry 3

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 119,144

F3 · 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.

F5 · balance_after: Includes 10,918 shares of restricted stock granted on December 3, 2021, 8,370 shares of restricted stock granted on December 15, 2022, and 14,204 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-028279 · form4.xml · nonDerivative · entry 2

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 122,881

F3 · 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.

F4 · balance_after: Includes 10,918 shares of restricted stock granted on December 3, 2021, 8,370 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-028279 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,180

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-027485 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 127,005

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-026150 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 126,831

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

F2 · balance_after: Includes 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-025574 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 126,665

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-024687 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 126,487

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-023987 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 126,300

F1 · price: 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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-023289 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 126,100

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-022350 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 125,910

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-021220 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 125,714

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-020514 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 125,535

F1 · price: 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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-019827 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 125,351

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-018896 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 125,160

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-017124 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 124,966

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-015629 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 124,774

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-013766 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 124,580

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-012990 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 124,406

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-011877 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 124,221

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 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-011378 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 124,032

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, 2024.

F2 · price: The number of shares represented by this award was determined by dividing the dollar value of the award granted to the Reporting Person by $8.80 (the volume-weighted average of the closing sale prices of the Issuer's common stock on the NYSE for each of the thirty (30) trading days immediately prior to the grant date).

F3 · balance_after: Includes 10,918 shares of restricted stock granted on December 3, 2021, 16,740 shares of restricted stock granted on December 15, 2022, and 21,306 shares of restricted stock granted on March 26, 2024.

SEC source: 0001127602-24-010601 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 102,726

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 10,918 shares of restricted stock granted on December 3, 2021 and 16,740 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-24-007812 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 102,542

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 10,918 shares of restricted stock granted on December 3, 2021 and 16,740 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-24-005353 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 102,366

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 10,918 shares of restricted stock granted on December 3, 2021 and 16,740 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-24-002724 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 102,179

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 10,918 shares of restricted stock granted on December 3, 2021 and 16,740 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-24-001327 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 102,002

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 10,918 shares of restricted stock granted on December 3, 2021 and 16,740 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-24-000097 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 101,810

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

F2 · balance_after: Includes 10,918 shares of restricted stock granted on December 3, 2021 and 16,740 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-030003 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 101,625

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 10,918 shares of restricted stock granted on December 3, 2021 and 16,740 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-028698 · form4.xml · nonDerivative · entry 3

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 101,438

F3 · 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.

F5 · balance_after: Includes 10,918 shares of restricted stock granted on December 3, 2021 and 16,740 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-028698 · form4.xml · nonDerivative · entry 2

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 106,316

F3 · 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.

F4 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 16,740 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-028698 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 110,066

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-027573 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 109,853

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-026398 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 109,642

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-025883 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 109,435

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-024985 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 109,210

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-024297 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 109,011

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-023554 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 108,823

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-022716 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 108,646

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-021564 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 108,464

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-020722 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 108,275

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-019982 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 108,082

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-019016 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 107,888

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-017220 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 107,713

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-016127 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 107,523

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-014729 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 107,335

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-012992 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 107,158

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

SEC source: 0001127602-23-011693 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 106,975

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

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

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 106,810

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

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

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 106,626

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

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

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 106,470

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.

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

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 106,302

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

F2 · balance_after: Includes 21,836 shares of restricted stock granted on December 3, 2021 and 25,111 shares of restricted stock granted on December 15, 2022.