John Taylor Maloney Fitzgerald - 15 Jan 2026 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Role: President and CEO, Director
Signature: /s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald
Issuer symbol: KFS
Transactions as of: 15 Jan 2026
Net transactions value: +$2,505
Form type: 4
Filing time: 29 Jan 2026, 18:39:07 UTC
Previous filing: 05 Jan 2026
Next filing: 02 Feb 2026
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Fitzgerald John Taylor Maloney	President and CEO, Director	10 S. RIVERSIDE PLAZA, SUITE 1520, CHICAGO	/s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald	29 Jan 2026	0001584349

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	KFS	Common Stock	Purchase	$2,505	+185	+0.01%	$13.54	1,459,903	15 Jan 2026	Direct	F1, F2
holding	KFS	Common Stock						34,100	15 Jan 2026	Trust-GEF
holding	KFS	Common Stock						34,100	15 Jan 2026	Trust-LTF
holding	KFS	Common Stock						34,100	15 Jan 2026	Trust-MPF

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	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	Includes 400,000 shares of restricted stock granted on March 31, 2021.

Content

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