X0508 4 2024-11-29 0001072627 KINGSWAY FINANCIAL SERVICES INC KFS 0001686017 Hansen Kent A 10 S. RIVERSIDE PLAZA SUITE 1520 CHICAGO IL 60606 1 CFO & EVP 0 Common Stock 2024-11-29 4 P 0 175 8.95 A 127180 D Common Stock 2024-12-01 4 F 0 4299 8.83 D 122881 D Common Stock 2024-12-01 4 F 0 3737 8.83 D 119144 D 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. 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. 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. 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. 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. /s/ Debra Rouse, attorney-in-fact for Kent A. Hansen 2024-12-02