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

Rhea-AI Filing Summary

John Taylor Maloney Fitzgerald, President & CEO and a director of Kingsway Financial Services, Inc. (KFS), reported an open-market purchase of 176 shares of the company's common stock on 08/18/2025 at a price of $14.16 per share. After this transaction he beneficially owns 1,530,398 shares directly. The filing also shows indirect ownership of 20,000 shares each through three trusts (Trust-GEF, Trust-LTF, Trust-MPF).

The shares purchased were acquired under the Kingsway America Inc. Employee Share Purchase Plan (ESPP), which matches eligible employee contributions. The filing notes that the total beneficial ownership includes 400,000 shares of restricted stock granted on March 31, 2021. The Form 4 was signed on behalf of the reporting person by an attorney-in-fact on 08/18/2025.

Positive

• Insider purchase of 176 shares through the ESPP, indicating participation and alignment with employee-shareholder interests
• Company matching ESPP contributions provide automatic share accumulation for employees, as noted in the filing
• Disclosure of 400,000 restricted shares granted March 31, 2021, improves transparency around insider equity holdings

Negative

• None.

Insights

Securities Analyst

TL;DR: Routine ESPP purchase by the CEO increases direct stake modestly; no sales or unusual derivative activity reported.

The Form 4 documents a small open-market acquisition of 176 shares at $14.16 under the company ESPP, bringing direct beneficial ownership to 1,530,398 shares. There are no dispositions or derivative transactions disclosed. Inclusion of 400,000 restricted shares from a 2021 grant is material to calculating ultimate insiders' locked-in equity but the filing shows no change to those restricted shares. This is a routine insider buy consistent with employee plan participation rather than a separate discretionary purchase.

Corporate Governance Expert

TL;DR: Insider participation in the ESPP signals alignment with employees; the transaction is administrative and non-controversial.

As both an officer and director, the reporting person's purchase through the ESPP follows a pre-existing employee plan that includes company matching. The Form 4 is properly filed and signed by an attorney-in-fact. The disclosure that 400,000 restricted shares remain outstanding for the insider is relevant to governance and equity compensation oversight but the filing does not indicate any accelerated vesting or governance actions.

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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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)
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		176(1)	A	$14.16	1,530,398(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	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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
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FAQ

Who filed this Form 4 for KFS?

John Taylor Maloney Fitzgerald, President & CEO and director, with the form signed by attorney-in-fact Debra Rouse on 08/18/2025.

What transaction is reported on the KFS Form 4 dated 08/18/2025?

An open-market purchase of 176 shares of common stock at $14.16 per share, acquired under the company's ESPP.

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

The filing reports 1,530,398 shares beneficially owned following the reported transaction.

Does the filing disclose any restricted stock holdings for the insider?

Yes, the filing states it includes 400,000 shares of restricted stock granted on March 31, 2021.

Are there any derivative transactions or dispositions reported?

No. The Form 4 shows an acquisition via code P; there are no derivative securities or dispositions listed.