Joshua Horowitz - 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: +$2,268,750
SEC form: 4
Accepted by SEC: 18 Dec 2025, 16:15:19 UTC
Prior SEC filing: 12 Dec 2025
Next SEC filing: 05 Jan 2026
Source filing: View source filing
Reporting owner signature: /s/ Joshua Horowitz

Key filing fact

Joshua Horowitz filed Form 4 for KINGSWAY FINANCIAL SERVICES INC (KFS) on 18 Dec 2025.

Key facts

This page summarizes Joshua Horowitz's Form 4 filing for KINGSWAY FINANCIAL SERVICES INC (KFS).
4 reported transactions and 3 derivative rows are listed below.
Accepted by SEC: 18 Dec 2025, 16:15.

Change

Previous filing in this sequence was filed on 12 Dec 2025.
Current net transaction value: +$2,268,750.

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 0001612424 Primary reporting owner

Horowitz Joshua

Relationship: Director
Address: C/O PALM MANAGEMENT (US) LLC, 19 WEST ELM STREET, GREENWICH
Signature: /s/ Joshua Horowitz
Signature date: 18 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: $185,625
Shares: +22,500
Change %: +225%
Price: $8.25
Shares after: 32,500
Date: 17 Dec 2025
Ownership: Direct

KFS transaction

Common Stock

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

Transaction value: $2,083,125
Shares: +252,500
Change %: +220%
Price: $8.25
Shares after: 367,500
Date: 17 Dec 2025
Ownership: by Palm Global Small Cap Master Fund LP
Footnotes: F2

Reported derivative securities

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

KFS transaction Derivative

Stock Option (Right to Buy)

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

Transaction value: $0
Shares: -22,500
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 22,500
Exercise price: $8.25
Footnotes: F3

KFS transaction Derivative

Stock Option (Right to Buy)

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

Transaction value: $0
Shares: -252,500
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 17 Dec 2025
Ownership: by Palm Global Small Cap Master Fund LP
Underlying class: Common Stock
Underlying amount: 252,500
Exercise price: $8.25
Footnotes: F2, F3

KFS holding Derivative

Class D Preferred Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 14,000
Date: 17 Dec 2025
Ownership: Palm Global Small Cap Master Fund LP
Underlying class: Common Stock
Underlying amount: 36,842
Exercise price: $9.50
Footnotes: F1, F2

^* 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

The shares of Class D Preferred Stock, par value $0.01 per share (the "Class D Preferred Stock"), of Kingsway Financial Services Inc. (the "Company") have a stated value of $25 per share and are convertible at any time, at the holder's option, into shares of Common Stock, par value $0.01 per share, of the Company (the "Common Stock") at an initial conversion price of $9.50 per share (or 2.6316 shares of Common Stock for each share of Class D Preferred Stock), subject to customary adjustments. The Company has the option to redeem 25% of the outstanding shares of Class D Preferred Stock for cash upon the occurrence of certain events. All then-outstanding shares of Class D Preferred Stock shall be redeemed by the Company for cash on May 8, 2032.

Footnote F2

Palm Management (US) LLC, as the investment manager of Palm Global Small Cap Master Fund LP ("Palm Global"), may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Due to his positions as a portfolio manager and special limited partner of Palm Global and as an employee of Palm Management (US) LLC, Mr. Horowitz may be deemed to be a beneficial owner of the securities disclosed as directly owned by Palm Global. Palm Management (US) LLC and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein.

Footnote F3

On March 31, 2025, Mr. Horowitz and Palm Global entered into an option agreement with Stilwell Value LLC, (the "Option Agreement") to acquire 22,500 and 252,500 shares of Common Stock, respectively, at an exercise price of $8.25 per share, which Option Agreement was amended on December 17, 2025, to allow for the early exercise of the options. The options had an expiration of December 29, 2025 at 5:00 p.m. Eastern Time.