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.
The Kingsway Financial Services Inc. (NYSE: KFS) SEC filings page on Stock Titan provides access to the company’s U.S. regulatory documents, along with AI-powered tools to help interpret them. Kingsway files a range of forms with the Securities and Exchange Commission, reflecting its operations as a Search Fund–oriented owner of services businesses and its status as a New York Stock Exchange–listed issuer.
Investors can review current reports on Form 8-K that disclose material events such as quarterly and year-to-date financial results, acquisitions, and financing arrangements. For example, recent 8-K filings describe Kingsway’s results for the quarters ended June 30 and September 30, 2025, including reconciliations from GAAP net income (loss) to non-GAAP adjusted EBITDA, and provide details on the acquisition of Roundhouse Electric & Equipment Co., Inc. and related credit facilities.
The filings page also includes registration statements such as the S-1 covering the resale of common stock issued in a 2025 private placement and in connection with the acquisition of Bud’s Plumbing. This document outlines Kingsway’s business, segment structure, use of non-GAAP measures, and the terms under which selling stockholders may resell their shares.
Over time, users can expect to find Kingsway’s annual reports on Form 10-K and quarterly reports on Form 10-Q (when filed), which provide audited financial statements, segment information for Kingsway Search Xcelerator and Extended Warranty, and detailed risk factor and management discussion sections. Filings related to equity offerings, credit agreements, and other corporate actions are also part of the company’s EDGAR record.
Stock Titan’s interface is designed to surface AI-generated summaries that explain key points from lengthy filings, highlight segment performance, and clarify the implications of complex items such as non-GAAP adjustments, credit agreements, and registration rights. Users can quickly locate Forms 8-K, S-1, 10-K, 10-Q, and other documents, and explore insider and ownership-related disclosures when they are available in the SEC database.
For anyone analyzing KFS, this page offers a centralized view of Kingsway’s regulatory history, with real-time updates as new filings are posted to EDGAR and contextual AI insights to make the information more accessible.
Kingsway Financial Services Inc. reported an insider share sale by its President and CEO, John Taylor Maloney Fitzgerald, who is also a director. On 12/23/2025, he sold 30,000 shares of Kingsway common stock in an open market transaction coded as a sale at a price of $13.3238 per share.
After this transaction, he beneficially owned 1,459,534 shares directly, which include 400,000 shares of restricted stock granted on March 31, 2021. He also had indirect beneficial ownership of additional shares through trusts, including 34,100 shares held in each of three trusts identified as Trust‑GEF, Trust‑LTF, and Trust‑MPF.
Kingsway Financial Services Inc. insider Joseph Stilwell, a director and 10% owner, reported a sale of Common Stock. On 12/22/2025, Stilwell Associates, L.P. sold 19,229 shares of Kingsway common stock at $12.80 per share.
After this transaction, Stilwell reports 162,500 shares owned directly and additional indirect holdings of Kingsway common stock through several investment entities, including 300,000, 2,254,971, 436,911 and 371,568 shares. He also reports indirect interests in Kingsway preferred stock: Class D and Class C series with stated value of $25 per share, convertible into common stock at 2.63158 common shares per preferred share, with underlying amounts of 52,631, 88,421 and 16,842 common shares and redemption dates in 2032 as disclosed.
A holder of KFS common stock has filed a notice to sell shares under SEC Rule 144. The planned transaction covers 7,500 common shares through broker Charles Schwab Corp. on the NYSE, with an indicated aggregate market value of $105,000. The issuer lists 28,956,152 common shares outstanding.
The shares to be sold were acquired from the issuer as stock grants classified as equity compensation, with 7,436 shares granted on 12/01/2024 and 64 shares on 12/03/2024, both fully paid on the respective grant dates. The notice also states that the seller represents they are not aware of any undisclosed material adverse information about the issuer’s current or prospective operations.
KFS received a notice of proposed stock sales under Rule 144. A shareholder plans to sell 30,000 shares of common stock through Goldman Sachs & Co. LLC on or about 12/23/2025 on the NYSE, with an indicated aggregate market value of $398,400. The filing notes that 28,956,152 shares of this class were outstanding.
The shares to be sold were originally acquired in 2016 as restricted stock units granted as compensation by the issuer on multiple dates, with payment described as compensation rather than cash purchases. The signer represents that they are not aware of any undisclosed material adverse information about the issuer’s current or prospective operations.
Kingsway Financial Services Inc. insider Joseph Stilwell and affiliated funds reported option-related share transactions. On December 17, 2025, entities associated with Stilwell, a director and 10% owner, reported dispositions of Kingsway common stock at a price of $8.25 per share through stock options described as an obligation to sell.
Footnotes explain that on March 31, 2025, Stilwell Value LLC entered into three option agreements granting buyers options to purchase 815,000, 660,000, and 275,000 Kingsway common shares, each at an exercise price of $8.25, later amended on December 17, 2025 to be exercisable at any time before 5:00 p.m. Eastern on December 29, 2025. The filing also notes indirect ownership of Kingsway shares and preferred stock (Class C and D) by several Stilwell-managed limited partnerships, with those preferred shares convertible into common stock at a stated conversion basis of 2.63158 common shares per preferred share.
Oakmont Capital Inc., a 10% owner and director-level affiliate of Kingsway Financial Services Inc. (KFS), reported a transaction involving 500,000 shares of Kingsway common stock. On December 17, 2025, Oakmont entered into a stock option (an obligation to sell) covering 500,000 common shares at a price of $8.25 per share, pursuant to an Option Agreement with David Capital Partners Special Situation Fund, LP that is exercisable up to 5:00 p.m. Eastern Time on December 29, 2025. After this reported transaction, Oakmont directly beneficially owns 1,987,830 shares of common stock. Oakmont also holds Class B and Class C Preferred Stock that are each convertible into common stock at a rate of 2.63158 common shares per preferred share, with all Class B Preferred Stock subject to redemption on September 24, 2031 and all Class C Preferred Stock subject to redemption on February 12, 2032.
Oakmont Capital Inc., a director-level holder of Kingsway Financial Services Inc. (KFS), reported an indirect sale-related transaction involving 500,000 common shares at $8.25 per share on December 17, 2025. The filing shows these shares as disposed of and reflects that 1,987,830 common shares are now indirectly held through Oakmont, with an additional 34,750 common shares held indirectly through a retirement plan.
The report also details derivative securities held indirectly by Oakmont. These include Class B Preferred Stock convertible into 210,526.4 common shares, redeemable by the company on September 24, 2031, and Class C Preferred Stock convertible into 105,263.2 common shares, redeemable on February 12, 2032. A stock option representing an obligation to sell 500,000 common shares at $8.25, linked to an option agreement with David Capital Partners Special Situation Fund, LP, is shown with zero derivative securities remaining after the reported transaction.
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.