13D Filings
KINGSWAY FINANCIAL SERVICES INC
KFS
Amendment
Ownership

1.50%

Total Shares

436,842

Issuer CIK

1072627

CUSIP

496904202

Event Date

Dec 16, 2025

Accepted

Dec 18, 2025, 04:15 PM

Reporting Persons (4)
Joint Filing

This is a joint filing. The reported shares may overlap between reporting persons and should not be summed.

NameType% of ClassAggregateSole VotingShared Voting
Joshua S. Horowitz
Individual
1.50%436,84232,500367,500
Palm Management (US) LLC
Other
1.40%404,3420367,500
Palm Global Small Cap Master Fund LP
Partnership
1.40%404,3420367,500
Bradley C. Palmer
Individual
1.40%404,3420367,500
Disclosure Items (6)

Security Title

Common Stock, par value $0.01 per share

Issuer Name

KINGSWAY FINANCIAL SERVICES INC

Issuer Address

10 S. Riverside Plaza, Chicago, IL, 60606

The total cost for acquiring the shares of Common Stock upon the exercise of outstanding options, as described in Item 4, was $2,083,125 for Palm Global and $185,625 for Mr. Horowitz. The source of funds for Palm Global was working capital, and the source of funds for Mr. Horowitz was personal funds.

On March 31, 2025, certain purchasers, including Palm Global and Mr. Horowitz, entered into option agreements with Stilwell Value LLC, an affiliate of Mr. Stilwell, to acquire an aggregate of 1,750,000 additional shares of Common Stock, at an exercise price of $8.25 per share, which options were exercisable by each investor (and Palm Global and Mr. Horowitz together) in whole, and not in part, on December 29, 2025 and were set to expire at 5:00 p.m. Eastern Time on December 29, 2025. On December 17, 2025, certain purchasers, including Palm Global and Mr. Horowitz, amended the option agreements to allow for the early exercise of the options. Following the amendment, on December 17, 2025 Palm Global exercised its options and purchased 252,500 shares of Common Stock and Mr. Horowitz exercised his options and purchased 22,500 shares of Common Stock. A copy of the amendment to the option agreement entered into by Palm Global and Mr. Horowitz is attached hereto as Exhibit 99.1. On May 8, 2025, Palm Global entered into a subscription agreement with the Company (the "Class D Subscription Agreement") for the purchase of shares of the Company's Preferred Stock. The shares of the Preferred Stock have a stated value of $25 per share and are convertible into shares of Common Stock at an initial conversion price of $9.50 per share (or 2.6316 shares of Common Stock for each share of Preferred Stock), subject to customary adjustments, at the option of the holder. For additional terms of the Preferred Stock and the Class D Subscription Agreement, see the form of the Class D Subscription Agreement and the Certificate of Designations of Preferred Stock, filed as Exhibit 99.2 and 99.3, respectively, to this Amendment No. 1. The Reporting Persons acquired the Common Stock reported in this Statement for investment purposes. The Reporting Persons and their affiliates may in the future acquire additional shares of Common Stock or dispose of some or all of the shares of Common Stock held by the Reporting Persons in open-market transactions or privately negotiated transactions, on such terms and at such times as the Reporting Persons may deem advisable. The Reporting Persons may engage in short selling or hedging or similar transactions with respect to the Common Stock, on such terms and at such times as the Reporting Persons may deem advisable, subject to applicable law. The Reporting Persons do not have any present plan or proposal that would relate to or result in any of the matters set forth in subparagraphs (a) - (j) of Item 4 of Schedule 13D except as set forth herein or such as would occur upon or in connection with completion of, or following, any of the actions discussed herein, or as may be proposed by Mr. Horowitz in his capacity as a director of the Company or by the Company's board of directors with his participation. The Reporting Persons intend to review their investment in the Company on a continuing basis. Depending on various factors including, without limitation, the Company's financial position, the price levels of the securities of the Company, conditions in the securities markets, and general economic and industry conditions, the Reporting Persons may in the future take such actions with respect to their investment in the Company as they deem appropriate and to the extent permitted by law, including, without limitation, engaging in communications with management and/or the board of directors of the Company and their advisors, engaging in discussions with stockholders of the Company and others about the Company and the Reporting Persons' investment, making proposals to the Company concerning changes to the capitalization, the ownership structure, the structure, composition and skill sets of the board of directors and senior management or the operations of the Company, purchasing additional securities of the Company, selling some or all of such securities, entering into financial instruments or other agreements that increase or decrease the Reporting Persons' economic or beneficial exposure with respect to their investment in the Company, engaging in short selling of or any hedging or similar transaction with respect to the securities of the Company, including swaps and other derivative instruments, or changing their intention with respect to any and all matters referred to in Item 4.

Percentage of Class

The Reporting Persons beneficially own in the aggregate 436,842.4 shares of Common Stock, which represents approximately 1.5% of the Company's outstanding shares of Common Stock. Palm Global directly holds the number and percentage of shares of Common Stock disclosed as beneficially owned by it in the applicable table set forth on the cover page to this Statement. Mr. Horowitz directly holds the number and percentage of shares of Common Stock disclosed as solely beneficially owned by him in the applicable table set forth on the cover page to this Statement. None of the other Reporting Persons directly holds any of the shares of Common Stock disclosed in this Statement. The Reporting Persons' holdings include 36,842.4 shares of Common Stock that may be acquired upon the conversion of Preferred Stock held by Palm Global. The Preferred Stock is convertible into shares of Common Stock at an initial conversion price of $9.50 per share (or 2.6316 shares of Common Stock for each share of Preferred Stock), subject to customary adjustments, at the option of the holder. Palm Management (US) LLC, as the investment manager of Palm Global, may be deemed to be a beneficial owner of the shares of Common Stock disclosed as directly owned by Palm Global. Due to their positions with Palm Management (US) LLC and Palm Global, each of Mr. Palmer and Mr. Horowitz may be deemed to be a beneficial owner of the shares of Common Stock disclosed as directly owned by Palm Global. Palm Management (US) LLC, Mr. Palmer and Mr. Horowitz expressly disclaim such beneficial ownership except to the extent of their pecuniary interest therein. Each percentage ownership of Common Stock set forth in this Statement is based on 28,956,152 shares of Common Stock reported by the Company as outstanding on November 6, 2025 in its Quarterly Report on Form 10-Q for the quarter ended September 30, 2025, filed with the Securities and Exchange Commission on November 6, 2025.

Number of Shares

Palm Global beneficially owns, and has the shared power to direct the voting and disposition of, the shares of Common Stock disclosed as beneficially owned by it in the applicable table set forth on the cover page to this Statement. Palm Management (US) LLC, as the investment manager of Palm Global, has the shared power to direct the voting and disposition of the shares of Common Stock held by Palm Global. Due to their positions with Palm Management (US) LLC and Palm Global, each of Mr. Palmer and Mr. Horowitz may be deemed to have the shared power to direct the voting and disposition of the shares of Common Stock held by Palm Global. Mr. Horowitz has the sole power to direct the voting and disposition of the shares of Common Stock disclosed as solely beneficially owned by him in the applicable table set forth on the cover page to this Statement.

Transactions

The information set forth in Item 4 is incorporated herein by reference.

The information set forth in Item 4 is incorporated herein by reference. Pursuant to Rule 13d-1(k) promulgated under the Securities Exchange Act of 1934, as amended, the Reporting Persons have entered into an agreement with respect to the joint filing of this Statement, which agreement is set forth on the signature page to this Statement.

Exhibit 99.1 - Amendment No. 1 to Option Agreement, dated December 17, 2025, by and between Stilwell Value LLC, Stilwell Activist Fund, L.P., and Stilwell Activist Investments, L.P. as sellers, and Palm Global Small Cap Master Fund LP and Joshua S. Horowitz, as buyers. Exhibit 99.2 - Form of Subscription Agreement (incorporated by reference to the Company's Current Report on Form 8-K filed with the Securities and Exchange Commission on May 19, 2025). Exhibit 99.3 - Class D Certificate of Designations (incorporated by reference to the Company's Current Report on Form 8-K filed with the Securities and Exchange Commission on May 19, 2025).