Kingsway CEO buys 239 shares at $10.45 via plan

After the Aug. 31 buy under the employee plan, his direct holdings total 1,426,907 shares, plus three trusts holding 29,100 shares each.

Rhea-AI Filing Summary

KINGSWAY Corp (KWY) director and President & CEO John Taylor Maloney purchased 239 shares of Common Stock on August 31, 2026 at $10.45 per share, through the Kingsway America Inc. Employee Share Purchase Plan. Following this purchase, his direct holdings total 1,426,907 shares, including 300,000 restricted shares granted on March 31, 2021. The filing also reports three indirect holdings of 29,100 shares each in separate trusts.

Insider Trade Summary

Net Buyer: 239 shares

Net Buy 4 txns

Insider Fitzgerald John Taylor Maloney

Role President and CEO

Bought 239 shs ($2K)

Type	Security	Shares	Price	Value
Purchase	Common Stock F1, F2	239	$10.45	$2K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Common Stock — 1,426,907 shares (Direct); Common Stock — 29,100 shares (Indirect, Trust-GEF); Common Stock — 29,100 shares (Indirect, Trust-LTF); Common Stock — 29,100 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 Corporation 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 300,000 shares of restricted stock granted on March 31, 2021.

Key Figures

Shares purchased: 239 shares of Common Stock Purchase price per share: $10.45 per share Direct holdings after transaction: 1,426,907 shares of Common Stock +2 more

5 metrics

Shares purchased 239 shares of Common Stock Purchase on August 31, 2026 under the ESPP

Purchase price per share $10.45 per share Common Stock bought on August 31, 2026

Direct holdings after transaction 1,426,907 shares of Common Stock Direct ownership following August 31, 2026 purchase

Restricted stock included in direct holdings 300,000 shares of restricted stock Granted on March 31, 2021 and included in direct total

Indirect trust holdings per trust 29,100 shares of Common Stock Post‑transaction position in each of three trusts (GEF, LTF, MPF)

Key Terms

Employee Share Purchase Plan, restricted stock, indirect

3 terms

Employee Share Purchase Plan financial

"The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan"

A program that lets employees buy their employer’s stock, often through regular payroll deductions and sometimes at a discounted price or with matching contributions; think of it as a company-run savings plan that converts part of pay into ownership. It matters to investors because it can increase insider ownership and employee motivation, potentially affecting company performance, and can slightly change share supply when new stock is issued or sold.

restricted stock financial

"Includes 300,000 shares of restricted stock granted on March 31, 2021."

Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.

indirect financial

"Common Stock ... indirect ... nature_of_ownership": "Trust-GEF""

FAQ

What insider transaction did KWY report for John Taylor Maloney?

John Taylor Maloney, President & CEO of KINGSWAY Corp, purchased 239 shares of Common Stock on August 31, 2026 at $10.45 per share under the company’s Employee Share Purchase Plan.

How many KWY shares does John Taylor Maloney hold after this transaction?

After the reported purchase, John Taylor Maloney’s direct ownership in KINGSWAY Corp totals 1,426,907 shares of Common Stock, which includes 300,000 shares of restricted stock granted on March 31, 2021.

Were the KWY shares bought on the open market or from the company?

The filing states the shares were acquired under the Employee Share Purchase Plan and that the plan administrator buys shares on the open market through a registered stockbroker using employee and company matching contributions.

Does John Taylor Maloney have indirect ownership of KWY shares?

Yes. The Form 4 reports three indirect positions of 29,100 shares of Common Stock each, held through trusts identified as Trust‑GEF, Trust‑LTF, and Trust‑MPF.

Is this KWY insider transaction part of a Rule 10b5-1 trading plan?

No. The Rule 10b5‑1 checkbox is not marked as an affirming plan, and the footnotes describe the purchase as occurring under the Employee Share Purchase Plan rather than under a Rule 10b5‑1 trading arrangement.

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

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Available on EDGAR 09/01/2026 - 05:03 PM Accepted by SEC EDGAR 09/01/2026 - 05:02 PM 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 ILLINOIS 60606

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
KINGSWAY Corp [ KWY ]

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
08/31/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	08/31/2026		P		239(1)	A	$10.45	1,426,907(2)	D
Common Stock								29,100	I	Trust-GEF
Common Stock								29,100	I	Trust-LTF
Common Stock								29,100	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 Corporation The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

2. Includes 300,000 shares of restricted stock granted on March 31, 2021.

	/s/ Debra S. Rouse, attorney-in-fact for John Taylor Maloney Fitzgerald	09/01/2026
	** 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.
* Form 4: SEC 1474 (03-26)