Welcome to our dedicated page for Kingsway Finl SEC filings (Ticker: KFS), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
Kingsway Financial Services, Inc. filings document an operating company that uses a Search Fund model to acquire and operate B2B and B2C services businesses. Form 8-K disclosures cover operating results and financial condition, including segment reporting for Kingsway Search Xcelerator and Extended Warranty, as well as material-event and Regulation FD updates tied to governance and board leadership.
Proxy materials describe director elections, auditor ratification, executive compensation votes, equity incentive plan matters, and certificate-of-incorporation amendments. Registration and capital-structure filings address common stock listed under KFS on the New York Stock Exchange, securities registration mechanics, offering disclosures, and related risk and governance information.
Oakmont Capital Inc., a director of Kingsway Financial Services Inc. (KFS), reported a significant change in its holdings of the company’s common stock. On December 17, 2025, Oakmont disposed of 500,000 shares of common stock at $8.25 per share through a stock option arrangement and reported indirect ownership of 1,987,830 common shares afterward, held through Oakmont.
Oakmont also reports additional indirect holdings of common stock through a retirement plan, spouse, and a trust. Beyond common shares, Oakmont holds Class B Preferred Stock with a stated value of $25 per share, convertible into 2.63158 common shares per preferred share and redeemable on September 24, 2031, and Class C Preferred Stock with the same conversion terms, redeemable on February 12, 2032.
The transaction stems from an option agreement with David Capital Partners Special Situation Fund, LP, originally dated March 31, 2025 and amended on December 17, 2025 so the option to purchase the 500,000 common shares at $8.25 can be exercised at any time before 5:00 p.m. Eastern Time on December 29, 2025.
Kingsway Financial Services Inc. (KFS) remains a significant holding for the Stilwell group, which reports beneficial ownership of 3,703,073 common shares, including 105,263 shares issuable from Class C Preferred Stock and 52,631 from Class D Preferred Stock that are immediately convertible. This position represents approximately 12.7% of Kingsway’s common shares, calculated using 28,956,152 shares outstanding as of November 6, 2025 plus the convertible preferred shares.
The filing explains that the Stilwell entities have been long‑term activist investors in Kingsway, with Joseph Stilwell serving as a director since 2009. Members of the group recently sold shares under option agreements originally dated March 31, 2025 and amended on December 17, 2025; the buyers exercised their options on the same day. The group states that it has achieved its goal of profiting from share price appreciation through asserting shareholder rights and now intends to gradually reduce its position over time, though it may still make additional purchases or sales depending on future decisions.
Kingsway Financial Services Inc. reported that its CFO and EVP, Kent A. Hansen, acquired additional common shares through the company’s employee share purchase plan. On 12/16/2025, he bought 122 shares of common stock at $12.82 per share in an open-market purchase coded as an acquisition. Following this transaction, he beneficially owns 136,472 common shares.
The shares were acquired under the Kingsway America Inc. Employee Share Purchase Plan, which allows eligible employees to contribute up to 5% of adjusted salary, with a 100% company match after 12 months of employment, and those contributions are used to buy Kingsway shares on the open market. His total holdings include 8,370 restricted shares granted on December 15, 2022, 14,204 restricted shares granted on March 26, 2024, and 20,728 restricted shares granted on December 4, 2024.
David Capital Partners and affiliates report a significant stake in Kingsway Financial Services Inc. They disclose beneficial ownership of 2,615,421.08 shares of common stock, representing approximately 9.0% of Kingsway’s outstanding common shares, including 68,421.08 shares that may be acquired by converting Class D Preferred Stock.
The filing explains that David Capital Partners Fund, LP and David Capital Partners Special Situation Fund, LP exercised amended option agreements on December 17, 2025 to buy, respectively, 275,000 and 1,040,000 shares of Kingsway common stock at an exercise price of $8.25 per share. DCP Special also holds Class D Preferred Stock, which is convertible into common stock at an initial conversion price of $9.50 per share. The reporting persons state that the position is held for investment purposes and that they may buy or sell additional shares, or use hedging and derivative strategies, depending on market and company conditions.
Kingsway Financial Services Inc. insider John Taylor Maloney Fitzgerald, who serves as President, CEO and Director, reported acquiring additional common shares. On 12/16/2025 he acquired 195 shares of common stock at a price of $12.82 per share, increasing his directly held position to 1,489,534 common shares.
He also reports indirect ownership of 34,100 common shares in each of three separate trusts (Trust-GEF, Trust-LTF and Trust-MPF. According to the notes, the acquired shares were purchased under the Kingsway America Inc. Employee Share Purchase Plan, under which eligible employees can contribute up to 5% of adjusted salary and receive a 100% company match after 12 months of employment. The filing states that the total direct holdings include 400,000 shares of restricted stock granted on March 31, 2021.
Kingsway Financial Services director Adam Jonathan Patinkin reported indirect acquisitions of the company’s common stock through investment funds he manages. On December 17, 2025, David Capital Partners Fund, LP exercised options to acquire 275,000 shares at $8.25 per share, and David Capital Partners Special Situation Fund, LP exercised options to acquire an additional 540,000 and 500,000 shares at the same price. The funds also hold 26,000 shares of Class D Preferred Stock, each convertible into 2.63158 common shares, with all outstanding Class D Preferred Stock scheduled to be redeemed by Kingsway on May 8, 2032.
Palm Global Small Cap Master Fund LP, Palm Management (US) LLC, Bradley C. Palmer and Joshua S. Horowitz report beneficial ownership of 436,842.4 Kingsway Financial common shares, about 1.5% of the 28,956,152 shares outstanding as of November 6, 2025. Their holdings include 36,842.4 shares that may be obtained by converting Class D Preferred Stock at an initial price of $9.50 per share, or 2.6316 common shares per preferred share.
On March 31, 2025 they entered option agreements to buy up to 1,750,000 shares at $8.25. After a December 17, 2025 amendment allowing early exercise, Palm Global bought 252,500 shares and Mr. Horowitz bought 22,500 shares. The exercise cost was $2,083,125 for Palm Global (from working capital) and $185,625 for Mr. Horowitz (from personal funds). The group states the investment is for investment purposes but may buy or sell more stock, use hedging or short selling, and engage with the company’s board and other stockholders.
Kingsway Financial Services Inc. director Joshua Horowitz reported exercising options on 12/17/2025 to acquire 22,500 shares of common stock at $8.25 per share, increasing his direct holdings to 32,500 common shares.
On the same date, Palm Global Small Cap Master Fund LP acquired 252,500 common shares at $8.25, resulting in 367,500 common shares reported as indirectly owned, with Palm Management (US) LLC and Mr. Horowitz stating they may be deemed beneficial owners through Palm Global but expressly disclaiming beneficial ownership beyond their pecuniary interest. Palm Global also holds 14,000 shares of Class D Preferred Stock, each with a stated value of $25 and initially convertible into 2.6316 common shares at a conversion price of $9.50 per share, with all then-outstanding Class D Preferred Stock to be redeemed for cash on May 8, 2032.
Kingsway Financial Services Inc. received an updated ownership disclosure from a shareholder group led by Oakmont Capital Inc. In an option agreement exercised on December 17, 2025, Oakmont sold 500,000 Kingsway common shares to David Capital Partners Special Situation Fund, LP at US$8.25 per share.
After this transaction, the group comprising Oakmont, E.J.K. Holdings Inc., 1272562 Ontario Inc., Terence M. Kavanagh and Gregory P. Hannon is reported to beneficially own 2,386,119 shares, or about 8.24% of Kingsway’s outstanding common stock as of that date. This percentage is based on 28,956,152 shares outstanding as of November 6, 2025, plus 315,789 shares issuable upon exercise of the group’s Series B warrants and conversion of its Class C preferred shares.
Kingsway Financial Services Inc. director and 10% owner Joseph Stilwell, together with affiliated fund Stilwell Associates, L.P., reported sales of Kingsway common stock on December 15 and 16, 2025. Associates sold 34,269 shares at $12.8005 on December 15 and 10,429 shares at $12.80 on December 16.
After these trades, the report shows Stilwell directly owning 162,500 Kingsway common shares and indirect interests in several large positions, including 545,135 shares held by Stilwell Associates, 3,550,382 shares held by Stilwell Activist Investments, L.P., 457,181 shares held by Stilwell Activist Fund, L.P., and 590,410 shares held by Stilwell Value Partners VII, L.P. He reports these as indirectly owned through his role at Stilwell Value LLC and disclaims beneficial ownership beyond his pecuniary interest.
The filing also lists indirect holdings of 20,000 shares of Class D Preferred Stock and 33,600 and 6,400 shares of Class C Preferred Stock. The Class C and Class D Preferred Stock each have a stated value of $25 per share and are convertible at any time into Kingsway common stock at a conversion basis of 2.63158 common shares per preferred share, with all outstanding Class D Preferred Stock to be redeemed on May 7, 2032 and all outstanding Class C Preferred Stock to be redeemed on February 12, 2032.