[Form 4] KINGSWAY FINANCIAL SERVICES INC Insider Trading Activity

Rhea-AI Filing Summary

John Taylor Maloney Fitzgerald, President & CEO and Director of Kingsway Financial Services Inc. (KFS), acquired 174 shares of KFS common stock on 09/15/2025 at $14.36 per share under the company's Employee Share Purchase Plan (ESPP). The ESPP allows employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months; purchases are executed on the open market by the plan administrator. After the transaction, Mr. Fitzgerald beneficially owns 1,530,745 shares, which includes 400,000 shares of restricted stock granted on March 31, 2021. The Form 4 was signed by an attorney-in-fact on behalf of Mr. Fitzgerald on 09/16/2025.

Positive

• CEO and Director participated in the company's ESPP, demonstrating continued personal investment in the company
• Substantial total beneficial ownership of 1,530,745 shares, including 400,000 restricted shares, signaling alignment with shareholders
• Purchase executed under ESPP with company matching contributions, reflecting structured and pre-approved acquisition

Negative

• None.

Insights

Financial Analyst

TL;DR: CEO purchased a small block (174 shares) via ESPP, maintaining a substantial overall stake (1.53M shares), signalling routine insider participation.

The purchase of 174 shares at $14.36 under the ESPP represents routine participation in a company-sponsored plan rather than a discretionary open-market buy by the executive. The reported total beneficial ownership of 1,530,745 shares, including 400,000 restricted shares, indicates significant insider alignment with shareholder interests. The transaction size is immaterial relative to the total stake and likely has negligible immediate market impact, but continued participation in the ESPP is a constructive governance signal.

Corporate Governance Expert

TL;DR: Transaction is standard ESPP activity for an executive; disclosure and filing appear complete and timely.

The Form 4 discloses the purchase pursuant to the ESPP and notes the employer match and market execution by the plan administrator. The filing lists the reporting person as both President & CEO and Director, and includes attorney-in-fact signature, which is a common administrative practice. Material governance concerns are not evident from this single, planned-plan purchase; monitoring future insider activity and any changes in restricted share schedules would be prudent for assessing longer-term alignment.

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^*

Fitzgerald John Taylor Maloney

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President and CEO

3. Date of Earliest Transaction (Month/Day/Year)
09/15/2025

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	09/15/2025		P		174(1)	A	$14.36	1,530,745(2)	D
Common Stock								20,000	I	Trust-GEF
Common Stock								20,000	I	Trust-LTF
Common Stock								20,000	I	Trust-MPF

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

	/s/ Debra Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald	09/16/2025
	** 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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What did John Taylor Maloney Fitzgerald purchase on 09/15/2025?

He acquired 174 shares of KFS common stock on 09/15/2025 at a price of $14.36 per share.

How were the shares acquired by the reporting person?

The shares were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan (ESPP), with purchases made on the open market by the plan administrator.

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

Following the reported transaction, he beneficially owns 1,530,745 shares, which includes 400,000 restricted shares granted on March 31, 2021.

What is the reporting person's role at KFS?

The reporting person is listed as both a Director and the President and CEO of Kingsway Financial Services Inc.

Who signed the Form 4 and when was it filed?

The Form 4 was signed by Debra Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald and dated 09/16/2025.