Kingsway Financial (KFS) CEO adds 185 shares through employee stock plan

Rhea-AI Filing Summary

Kingsway Financial Services Inc. President and CEO Fitzgerald John Taylor Maloney reported a small open‑market purchase of company stock. On January 15, 2026, he acquired 185 shares of Common Stock at $13.54 per share through the Kingsway America Inc. Employee Share Purchase Plan.

Following this transaction, he directly beneficially owns 1,459,903 Common shares, which include 400,000 restricted shares granted on March 31, 2021. He also reports indirect ownership of 34,100 shares in each of three separate trusts (Trust‑GEF, Trust‑LTF, and Trust‑MPF).

Insider Trade Summary

Net Buyer: 185 shares ($2,505)

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 185 shs ($3K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	185	$13.54	$3K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,459,903 shares (Direct); Common Stock — 34,100 shares (Indirect, Trust-GEF)

Footnotes (1)

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

Form 4 Insider Transactions: What Each Field Means →

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)
01/15/2026

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	01/15/2026		P		185(1)	A	$13.54	1,459,903(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/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald	01/29/2026
	** 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 insider transaction did Kingsway (KFS) report on January 15, 2026?

Kingsway reported that President and CEO Fitzgerald John Taylor Maloney bought 185 Common shares on January 15, 2026 at $13.54 per share. The purchase was made through the Kingsway America Inc. Employee Share Purchase Plan on the open market.

How many Kingsway (KFS) shares does the CEO own after this Form 4?

After the reported transaction, the CEO directly owns 1,459,903 Kingsway Common shares. This total includes 400,000 restricted shares granted on March 31, 2021, as disclosed in the footnotes to the insider ownership table.

What is the Kingsway America Inc. Employee Share Purchase Plan (ESPP)?

The ESPP lets eligible employees contribute up to 5% of adjusted salary each payroll period, with a 100% company match after 12 months of employment. Employee and company contributions are used to buy Kingsway shares on the open market.

Were any derivative securities reported in this Kingsway (KFS) Form 4?

No derivative securities were reported. The Form 4’s Table II for derivatives is blank, and all disclosed holdings and the single transaction relate to Common Stock only, with no options, warrants, or other convertible instruments listed.

What indirect Kingsway (KFS) holdings does the CEO report in this filing?

The CEO reports indirect ownership of 34,100 Common shares in each of Trust‑GEF, Trust‑LTF, and Trust‑MPF. These positions are shown as indirect holdings, separate from his directly owned 1,459,903 Kingsway Common shares.

How are Kingsway (KFS) ESPP shares acquired for employees and the CEO?

ESPP shares are acquired by the plan administrator on the open market using employee and matching company contributions. Purchases are made “as soon as administratively practicable” after contributions through a duly registered stockbroker, then credited as Kingsway Common Stock.