John Taylor Maloney Fitzgerald - Dec 29, 2023 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Role: President and CEO, Director
Signature: /s/ Debra Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald
Stock symbol: KFS
Transactions as of: Dec 29, 2023
Transactions value $: $2,504
Form type: 4
Date filed: 1/2/2024, 03:56 PM
Previous filing: Dec 22, 2023
Next filing: Jan 16, 2024

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	KFS	Common Stock	Purchase	$2.5K	+296	+0.02%	$8.46	1.78M	Dec 29, 2023	Direct	F1, F2
holding	KFS	Common Stock						20K	Dec 29, 2023	Trust-GEF
holding	KFS	Common Stock						20K	Dec 29, 2023	Trust-LTF
holding	KFS	Common Stock						20K	Dec 29, 2023	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 500,000 shares of restricted stock issued on September 5, 2018 and 500,000 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 500,000 shares of restricted stock issued on September 5, 2018 and 500,000 shares of restricted stock granted on March 31, 2021.