Fitzgerald John Taylor Maloney

SEC source: 0001127602-25-007841 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,527,831

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 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-25-005190 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,527,516

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

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

SEC source: 0001127602-25-002606 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,527,205

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

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

SEC source: 0001127602-25-001430 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,526,905

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

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

SEC source: 0001127602-25-000086 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,526,604

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

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

SEC source: 0001127602-24-029632 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,526,307

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

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

SEC source: 0001127602-24-028281 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,526,016

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

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

SEC source: 0001127602-24-027483 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,525,737

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

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

SEC source: 0001127602-24-026152 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,525,458

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

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

SEC source: 0001127602-24-025573 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,525,192

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

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

SEC source: 0001127602-24-024689 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,524,908

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

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

SEC source: 0001127602-24-024518 · form4.xml · derivative · entry 5

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

10b5-1 filing: No plan indicated

Ownership: Indirect · BY FFI

Disclosed balance after: 8,000

Underlying: Common Stock · 21,052.8 shares

Expires 2031-09-24

F1 · derivative.exercise_price: The shares of Class B Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class B Preferred Stock, subject to customary adjustments. All outstanding shares of Class B Preferred Stock shall be redeemed by the Company on September 24, 2031.

F1 · derivative.expiration_date: The shares of Class B Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class B Preferred Stock, subject to customary adjustments. All outstanding shares of Class B Preferred Stock shall be redeemed by the Company on September 24, 2031.

F1 · derivative.underlying_shares: The shares of Class B Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class B Preferred Stock, subject to customary adjustments. All outstanding shares of Class B Preferred Stock shall be redeemed by the Company on September 24, 2031.

SEC source: 0001127602-25-005192 · form4a.xml · derivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Indirect · BY FFI

Disclosed balance after: 8,000

Underlying: Common Stock · 21,052.64 shares

Expires 2031-09-24

F1 · derivative.exercise_price: The shares of Class B Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class B Preferred Stock, subject to customary adjustments. All outstanding shares of Class B Preferred Stock shall be redeemed by the Company on September 24, 2031.

F1 · derivative.expiration_date: The shares of Class B Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class B Preferred Stock, subject to customary adjustments. All outstanding shares of Class B Preferred Stock shall be redeemed by the Company on September 24, 2031.

F1 · derivative.underlying_shares: The shares of Class B Preferred Stock of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class B Preferred Stock, subject to customary adjustments. All outstanding shares of Class B Preferred Stock shall be redeemed by the Company on September 24, 2031.

F2 · derivative.underlying_shares: This Form 4 amendment is adjusting the conversion basis to display results with five decimal places instead of the previous four due to a software glitch.

SEC source: 0001127602-24-023986 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,524,609

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 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-24-023760 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,524,289

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 400,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-24-023290 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,568,121

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 granted on March 31, 2021.

SEC source: 0001127602-24-022347 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,567,817

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 granted on March 31, 2021.

SEC source: 0001127602-24-021221 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,567,502

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 granted on March 31, 2021.

SEC source: 0001127602-24-020515 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,567,216

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-24-019826 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,566,922

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 granted on March 31, 2021.

SEC source: 0001127602-24-018895 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,566,617

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 granted on March 31, 2021.

SEC source: 0001127602-24-017123 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,566,307

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 granted on March 31, 2021.

SEC source: 0001127602-24-015627 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,565,999

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 granted on March 31, 2021.

SEC source: 0001127602-24-013765 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,565,689

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 granted on March 31, 2021.

SEC source: 0001127602-24-012993 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,565,410

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 granted on March 31, 2021.

SEC source: 0001127602-24-011876 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,565,114

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 granted on March 31, 2021.

SEC source: 0001127602-24-011466 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,564,812

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 granted on March 31, 2021.

SEC source: 0001127602-24-010600 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,785,916

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-24-007811 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,785,622

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-24-005350 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,785,340

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-24-002730 · form4a.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,785,041

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-24-002722 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,785,041

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-24-001325 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,784,758

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-24-000096 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,784,451

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-030335 · form4.xml · nonDerivative · entry 6

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

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust-MPF

Disclosed balance after: 20,000

F3 · kind: Transfer received of Kingsway Financial Services Inc. shares to child's trust.

SEC source: 0001127602-23-030335 · form4.xml · nonDerivative · entry 5

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,784,155

F1 · kind: Transfer of Kingsway Financial Services Inc. shares to child's trust.

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

SEC source: 0001127602-23-030335 · form4.xml · nonDerivative · entry 4

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

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust-GEF

Disclosed balance after: 20,000

F3 · kind: Transfer received of Kingsway Financial Services Inc. shares to child's trust.

SEC source: 0001127602-23-030335 · form4.xml · nonDerivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,804,155

F1 · kind: Transfer of Kingsway Financial Services Inc. shares to child's trust.

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

SEC source: 0001127602-23-030335 · form4.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Indirect · Trust-LTF

Disclosed balance after: 20,000

F3 · kind: Transfer received of Kingsway Financial Services Inc. shares to child's trust.

SEC source: 0001127602-23-030335 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,824,155

F1 · kind: Transfer of Kingsway Financial Services Inc. shares to child's trust.

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

SEC source: 0001127602-23-030000 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,844,155

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-028699 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,843,855

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-027571 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,843,514

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-026399 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,843,177

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-025884 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,842,845

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-024983 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,842,486

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-024295 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,842,168

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-023840 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,841,867

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 500,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-023557 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,885,760

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

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 600,000 shares of restricted stock granted on March 31, 2021.

SEC source: 0001127602-23-022717 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,885,477

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.