Gregory Paul Hannon - 17 Dec 2025 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Reporting relationship: Director
Issuer ticker: KFS
Reported as of: 17 Dec 2025
Net transaction value: -$4,125,000
SEC form: 4
Accepted by SEC: 19 Dec 2025, 19:13:04 UTC
Prior SEC filing: 17 Nov 2025
Next SEC filing: 05 Jan 2026
Source filing: View source filing
Reporting owner signature: /s/ Kent Hansen, as attorney-in-fact for Gregory Paul Hannon

Key filing fact

Gregory Paul Hannon filed Form 4 for KINGSWAY FINANCIAL SERVICES INC (KFS) on 19 Dec 2025.

Key facts

This page summarizes Gregory Paul Hannon's Form 4 filing for KINGSWAY FINANCIAL SERVICES INC (KFS).
2 reported transactions and 3 derivative rows are listed below.
Accepted by SEC: 19 Dec 2025, 19:13.

Change

Previous filing in this sequence was filed on 17 Nov 2025.
Current net transaction value: -$4,125,000.

Research use

This tells you what this filing adds before you inspect full transaction and derivative tables.
You can trace every row back to the original SEC filing document.

Evidence

Filed on Form 4

Ownership activity is grounded in SEC Form 4 disclosures.

View source filing

Reporting Owners (1)

CIK 0001538186 Primary reporting owner

Hannon Gregory Paul

Relationship: Director
Address: OAKMONT CAPITAL INC., 45 ST. CLAIR AVENUE WEST, SUITE 400, TORONTO, ONTARIO, CANADA
Signature: /s/ Kent Hansen, as attorney-in-fact for Gregory Paul Hannon
Signature date: 19 Dec 2025

Reported non-derivative transactions

Shares, units, or other non-derivative securities reported in this filing.

KFS transaction

Common Stock

Exercise of in-the-money or at-the-money derivative security

Transaction value: $4,125,000
Shares: -500,000
Change %: -20%
Price: $8.25
Shares after: 1,987,830
Date: 17 Dec 2025
Ownership: By Oakmont Capital Inc
Footnotes: F1

KFS holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 29,500
Date: 17 Dec 2025
Ownership: By Retirement Plan (R)

KFS holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 13,750
Date: 17 Dec 2025
Ownership: By Spouse

KFS holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 4,500
Date: 17 Dec 2025
Ownership: By Trust

Reported derivative securities

Options, warrants, convertible securities, or similar derivative positions disclosed in the filing.

KFS transaction Derivative

Stock Option (obligation to sell)

Exercise of in-the-money or at-the-money derivative security

Transaction value: $0
Shares: -500,000
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: By Oakmont Capital Inc.
Underlying class: Common Stock
Underlying amount: 500,000
Exercise price: $8.25
Footnotes: F1

KFS holding Derivative

Class B Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 80,000
Date: 17 Dec 2025
Ownership: By Oakmont Capital Inc.
Underlying class: Common Stock
Underlying amount: 210,526
Exercise price: $9.50
Footnotes: F2

KFS holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 40,000
Date: 17 Dec 2025
Ownership: By Oakmont Capital Inc.
Underlying class: Common Stock
Underlying amount: 105,263
Exercise price: $9.50
Footnotes: F3

^* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 3 footnotes

Footnote F1

On March 31, 2025, Oakmont Capital Inc. ("Oakmont") entered into an Option Agreement with David Capital Partners Special Situation Fund, LP ("DCPSS"), pursuant to which Oakmont granted DCPSS an option to purchase 500,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company") at an exercise price of $8.25 per share. The Option Agreement was set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and was amended on December 17, 2025 so that the option became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025.

Footnote F2

The shares of Class B Preferred Stock of the Company have a stated value of $25 per share and are convertible at any time into shares of Common Stock at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class B Preferred Stock, subject to customary adjustments. All outstanding shares of Class B Preferred Stock shall be redeemed by the Company on September 24, 2031.

Footnote F3

The shares of Class C Preferred Stock of the Company have a stated value of $25 per share and are convertible at any time into shares of Common Stock at a conversion basis equal to 2.63158 shares of Common Stock for each share of Class C Preferred Stock, subject to customary adjustments. All outstanding shares of Class C Preferred Stock shall be redeemed by the Company on February 12, 2032.