Kingsway (KFS) CEO acquires 157 shares at $15.92 via ESPP

Kingsway Financial Services (KFS) disclosed an insider transaction: President and CEO, and Director, John Taylor Maloney Fitzgerald acquired 157 shares of common stock on 10/15/2025 at $15.92 per share through the company’s Employee Share Purchase Plan.

Rhea-AI Filing Summary

Kingsway Financial Services (KFS) disclosed an insider transaction: President and CEO, and Director, John Taylor Maloney Fitzgerald acquired 157 shares of common stock on 10/15/2025 at $15.92 per share through the company’s Employee Share Purchase Plan. Following the trade, he beneficially owned 1,488,773 shares directly, and 34,100 shares each held indirectly via Trust‑GEF, Trust‑LTF, and Trust‑MPF. The holdings include 400,000 shares of restricted stock granted on March 31, 2021.

Insider Trade Summary

Net Buyer: 157 shares

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 157 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	157	$15.92	$2K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,488,773 shares (Direct); Common Stock — 34,100 shares (Indirect, Trust-GEF); Common Stock — 34,100 shares (Indirect, Trust-LTF); Common Stock — 34,100 shares (Indirect, Trust-MPF)

Footnotes (2)

1. 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.
2. F2. Includes 400,000 shares of restricted stock granted on March 31, 2021.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What did KFS’s CEO report on Form 4?

He acquired 157 shares of common stock on 10/15/2025 at $15.92 per share via the ESPP.

How many KFS shares does the CEO own after the transaction?

He beneficially owns 1,488,773 shares directly and 34,100 shares each indirectly via Trust‑GEF, Trust‑LTF, and Trust‑MPF.

What plan was used to acquire the shares?

The shares were acquired under the Employee Share Purchase Plan, which allows up to 5% salary contributions with a 100% company match after 12 months.

Were restricted shares included in the reported holdings?

Yes. The holdings include 400,000 shares of restricted stock granted on March 31, 2021.

What is the issuer and ticker for this filing?

The issuer is Kingsway Financial Services Inc. with ticker KFS.

What roles does the reporting person hold at KFS?

He is a Director and serves as President and CEO.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 10/17/2025 - 05:41 PM EDT Learn about SEC filing dates

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)
10/15/2025

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	10/15/2025		P		157(1)	A	$15.92	1,488,773(2)	D
Common Stock								34,100	I	Trust-GEF
Common Stock								34,100	I	Trust-LTF
Common Stock								34,100	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/ Robert E. Buckner II, attorney-in-fact for John Taylor Maloney Fitzgerald	10/17/2025
	** 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.