Stilwell Joseph - 17 Dec 2025 Form 4 Insider Report for KINGSWAY FINANCIAL SERVICES INC (KFS)

Reporting relationship: Director, 10%+ Owner
Issuer ticker: KFS
Reported as of: 17 Dec 2025
Net transaction value: -$14,437,500
SEC form: 4
Accepted by SEC: 19 Dec 2025, 19:50:06 UTC
Prior SEC filing: 17 Dec 2025
Next SEC filing: 29 Dec 2025
Source filing: View source filing
Reporting owner signature: /s/ Kent Hansen as Attorney-in-Fact for Joseph Stilwell

Key filing fact

Stilwell Joseph filed Form 4 for KINGSWAY FINANCIAL SERVICES INC (KFS) on 19 Dec 2025.

Key facts

This page summarizes Stilwell Joseph's Form 4 filing for KINGSWAY FINANCIAL SERVICES INC (KFS).
8 reported transactions and 7 derivative rows are listed below.
Accepted by SEC: 19 Dec 2025, 19:50.

Change

Previous filing in this sequence was filed on 17 Dec 2025.
Current net transaction value: -$14,437,500.

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 (6)

CIK 0001113303 Primary reporting owner

Stilwell Joseph

Relationship: Director, 10%+ Owner
Address: 200 CALLE DEL SANTO CRISTO, SAN JUAN, PUERTO RICO
Signature: /s/ Kent Hansen as Attorney-in-Fact for Joseph Stilwell
Signature date: 19 Dec 2025

CIK 0001397076

Stilwell Value LLC

Relationship: 10%+ Owner
Address: 111 BROADWAY, 12TH FLOOR, NEW YORK
Signature: /s/ Kent Hansen as Attorney-in-Fact for Stilwell Value LLC
Signature date: 19 Dec 2025

CIK 0000913960

Stilwell Associates, L.P.

Relationship: 10%+ Owner
Address: 111 BROADWAY, 12TH FLOOR, NEW YORK
Signature: /s/ Kent Hansen as Attorney-in-Fact for Stilwell Associates, L.P.
Signature date: 19 Dec 2025

CIK 0001564452

Stilwell Activist Fund, L.P.

Relationship: 10%+ Owner
Address: 111 BROADWAY, 12TH FLOOR, NEW YORK
Signature: /s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Fund, L.P.
Signature date: 19 Dec 2025

CIK 0001573720

Stilwell Activist Investments, L.P.

Relationship: 10%+ Owner
Address: 111 BROADWAY, 12TH FLOOR, NEW YORK
Signature: /s/ Kent Hansen as Attorney-in-Fact for Stilwell Activist Investments, L.P.
Signature date: 19 Dec 2025

CIK 0001555931

Stilwell Value Partners VII, L.P.

Relationship: 10%+ Owner
Address: 111 BROADWAY, 12TH FLOOR, NEW YORK
Signature: /s/ Kent Hansen as Attorney-in-Fact for Stilwell Value Partners VII, L.P.
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: $1,777,685
Shares: -215,477
Change %: -40%
Price: $8.25
Shares after: 319,229
Date: 17 Dec 2025
Ownership: See footnote
Footnotes: F2, F3

KFS transaction

Common Stock

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

Transaction value: $10,687,141
Shares: -1,295,411
Change %: -36%
Price: $8.25
Shares after: 2,254,971
Date: 17 Dec 2025
Ownership: See footnote
Footnotes: F2, F4

KFS transaction

Common Stock

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

Transaction value: $167,228
Shares: -20,270
Change %: -4.4%
Price: $8.25
Shares after: 436,911
Date: 17 Dec 2025
Ownership: See footnote
Footnotes: F2, F5

KFS transaction

Common Stock

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

Transaction value: $1,805,446
Shares: -218,842
Change %: -37%
Price: $8.25
Shares after: 371,568
Date: 17 Dec 2025
Ownership: See footnote
Footnotes: F2, F6

KFS holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 162,500
Date: 17 Dec 2025
Ownership: Direct
Footnotes: F1

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: -215,477
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: See footnote
Underlying class: Common Stock
Underlying amount: 215,477
Exercise price: $8.25
Footnotes: F2, F3

KFS transaction Derivative

Stock Option (obligation to sell)

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

Transaction value: $0
Shares: -1,295,411
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: See footnote
Underlying class: Common Stock
Underlying amount: 1,295,411
Exercise price: $8.25
Footnotes: F2, F4

KFS transaction Derivative

Stock Option (obligation to sell)

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

Transaction value: $0
Shares: -20,270
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: See footnote
Underlying class: Common Stock
Underlying amount: 20,270
Exercise price: $8.25
Footnotes: F2, F5

KFS transaction Derivative

Stock Option (obligation to sell)

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

Transaction value: $0
Shares: -218,842
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: See footnote
Underlying class: Common Stock
Underlying amount: 218,842
Exercise price: $8.25
Footnotes: F2, F6

KFS holding Derivative

Class D Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 20,000
Date: 17 Dec 2025
Ownership: See footnote
Underlying class: Common Stock
Underlying amount: 52,631
Exercise price: $9.50
Footnotes: F3, F7

KFS holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 33,600
Date: 17 Dec 2025
Ownership: See footnote
Underlying class: Common Stock
Underlying amount: 88,421
Exercise price: $9.50
Footnotes: F4, F8

KFS holding Derivative

Class C Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 6,400
Date: 17 Dec 2025
Ownership: See footnote
Underlying class: Common Stock
Underlying amount: 16,842
Exercise price: $9.50
Footnotes: F5, F8

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

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 8 footnotes

Footnote F1

These are shares owned directly by Joseph Stilwell.

Footnote F2

On March 31, 2025, Stilwell Value LLC ("Value") entered into three Option Agreements with certain counterparties (collectively, the "Buyers"), pursuant to which Value granted each Buyer an option to purchase, respectively, (i) 815,000 shares of common stock, par value $0.01 per share (the "Common Stock"), of Kingsway Financial Services Inc. (the "Company"), (ii) 660,000 shares of Common Stock, and (iii) 275,000 shares of Common Stock, at an exercise price of $8.25 per share. The Option Agreements were set to expire at 5:00 p.m. Eastern Time on December 29, 2025, and were amended on December 17, 2025 so that the options became exercisable at any time prior to 5:00 p.m. Eastern Time on December 29, 2025.

Footnote F3

These are shares owned directly by Stilwell Associates, L.P. ("Associates") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Footnote F4

These are shares owned directly by Stilwell Activist Investments, L.P. ("SAI") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Footnote F5

These are shares owned directly by Stilwell Activist Fund, L.P. ("SAF") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Footnote F6

These are shares owned directly by Stilwell Value Partners VII, L.P. ("SVP VII") and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Footnote F7

The shares of Class D 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 D Preferred Stock, subject to customary adjustments. All outstanding shares of Class D Preferred Stock shall be redeemed by the Company on May 7, 2032.

Footnote F8

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.