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

Rhea-AI Filing Summary

Kent A. Hansen, Chief Financial Officer and EVP of Kingsway Financial Services Inc. (KFS), purchased shares under the company's Employee Share Purchase Plan (ESPP). On 08/29/2025 Mr. Hansen acquired 107 shares of KFS common stock at $14.49 per share through the ESPP. After the purchase he beneficially owns 135,682 shares, which includes restricted stock grants of 8,370, 14,204, and 20,728 shares granted on December 15, 2022, March 26, 2024, and December 4, 2024, respectively. The ESPP permits eligible employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months of employment; shares are bought on the open market by the plan administrator. The Form 4 was signed by an attorney-in-fact for Mr. Hansen on 09/02/2025.

Positive

• Insider purchase under ESPP—CFO Kent A. Hansen acquired 107 shares at $14.49, showing participation in company equity program
• Clear disclosure of restricted shares—filing itemizes prior restricted grants totaling 43,302 shares (8,370 + 14,204 + 20,728), clarifying insider holdings

Negative

• None.

Insights

Financial Analyst

TL;DR: A routine, modest insider purchase via ESPP increases management ownership slightly; not material to valuation on its own.

The acquisition of 107 shares at $14.49 under the ESPP is an insider purchase but small relative to total beneficial ownership of 135,682 shares. The disclosure confirms participation in a company-sponsored plan with a matching contribution, which aligns executive and shareholder interests. There is no evidence of derivative transactions or disposals in this filing. Overall, this Form 4 signals routine compensation participation rather than a material corporate event.

Corporate Governance Expert

TL;DR: Insider participation in the ESPP is governance-positive but not materially impactful given the modest purchase size.

Mr. Hansen's purchase under the ESPP reflects standard equity-based compensation design and increases his direct stake in KFS. The filing also transparently reports restricted share holdings from prior grants, which helps clarify the insider's long-term incentive alignment. There are no governance red flags in this filing; signature by an attorney-in-fact is a common administrative practice.

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
Estimated average burden
hours per response:			0.5

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)
08/29/2025

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	08/29/2025		P		107(1)	A	$14.49	135,682(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	09/02/2025
	** 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?

Mr. Hansen reported acquiring 107 shares of Kingsway Financial Services Inc. common stock on 08/29/2025 at a price of $14.49 per share under the ESPP.

How many KFS shares does the reporting person beneficially own after the transaction?

Following the reported transaction Mr. Hansen beneficially owns 135,682 shares of KFS common stock.

What restricted stock grants are included in the beneficial ownership total?

The beneficial ownership total includes restricted stock grants of 8,370 shares (12/15/2022), 14,204 shares (03/26/2024), and 20,728 shares (12/04/2024).

Under what plan were the 107 shares acquired?

The shares were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan (ESPP), which allows employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months of employment.

Who signed the Form 4 filing for Mr. Hansen?

The Form 4 was signed by Debra Rouse, attorney-in-fact for Kent A. Hansen on 09/02/2025.