[Form 4] Kingsway Financial Services, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Kent A. Hansen, CFO & EVP of Kingsway Financial Services Inc. (KFS), reported an ESPP purchase on 08/18/2025. The filing shows an acquisition of 111 shares at $14.16 under the Kingsway America Inc. Employee Share Purchase Plan, which provides a company match for eligible employees. After the transaction the filing reports beneficial ownership of 135,575 shares, which includes previously granted restricted shares totaling 43,302 shares from 2022 and 2024 awards. The form was signed by an attorney-in-fact.

Positive

• Insider participation in ESPP demonstrates alignment with company equity programs
• Company match described (100% of employee contribution), indicating incented employee ownership
• Clear disclosure of restricted stock balance (43,302 shares) included in total beneficial ownership

Negative

• None.

Insights

Securities Analyst

TL;DR: Insider used the company ESPP to modestly increase holdings; total beneficial ownership is disclosed and includes restricted awards.

The Form 4 documents a routine employee purchase of 111 shares at $14.16 under the company's ESPP on 08/18/2025. The report clarifies that the reported post-transaction beneficial ownership of 135,575 shares incorporates restricted stock grants from 2022 and 2024 totaling 43,302 shares. This filing is a standard Section 16 disclosure and does not indicate other compensatory arrangements or derivative activity.

Corporate Governance Expert

TL;DR: Compliance filing appears complete and cites the ESPP matching mechanics and restricted stock composition of holdings.

The disclosure cites the Kingsway America Inc. ESPP terms: employees may contribute up to 5% of adjusted salary and eligible employees receive a 100% company match. The administrator purchases shares on the open market through a broker. The signature by an attorney-in-fact is noted, which is acceptable practice when properly authorized. No material governance issues or unusual transactions are disclosed in this Form 4.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Hansen Kent A

(Last) (First) (Middle)

10 S. RIVERSIDE PLAZA

SUITE 1520

(Street)

CHICAGO IL 60606

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
KINGSWAY FINANCIAL SERVICES INC [ KFS ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	CFO & EVP

3. Date of Earliest Transaction (Month/Day/Year)
08/18/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	08/18/2025		P		111(1)	A	$14.16	135,575(2)	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. 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.

2. Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

	/s/ Debra Rouse, attorney-in-fact for Kent A. Hansen	08/18/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
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FAQ

What transaction did Kent A. Hansen report on Form 4 for KFS?

The Form 4 reports an ESPP purchase of 111 shares at $14.16 on 08/18/2025.

How many KFS shares does the filing say Kent Hansen beneficially owns after the transaction?

The filing reports beneficial ownership of 135,575 shares following the reported transaction.

What restricted stock grants are included in Hansen's reported ownership?

The total includes 8,370 shares granted on 12/15/2022, 14,204 shares on 3/26/2024, and 20,728 shares on 12/4/2024.

What are key terms of the Kingsway ESPP described in the filing?

Eligible employees may contribute up to 5% of adjusted salary and, after 12 months of employment, receive a 100% company match; shares are purchased on the open market by the plan administrator.

Who signed the Form 4 for Kent Hansen?

The form was signed by Debra Rouse, attorney-in-fact for Kent A. Hansen on 08/18/2025.