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.
Kingsway Financial Services Inc. insider trading report shows the company’s Chief Financial Officer and Executive Vice President, Kent A. Hansen, acquired additional common shares on 12/31/2025. The filing reports a purchase of 115 shares of Kingsway common stock at a price of $13.58 per share, bringing his total directly held beneficial ownership to 119,477 shares.
The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan, which allows eligible employees to contribute up to 5% of adjusted salary, with the company matching 100% of contributions for employees with at least 12 months of service. The filing notes that this ownership total includes 7,102 restricted shares granted on March 26, 2024 and 13,818 restricted shares granted on December 4, 2024.
Kingsway Financial Services Inc. President and CEO John Taylor Maloney Fitzgerald reported a small open‑market acquisition of company stock through an employee plan. On 12/31/2025, he acquired 184 shares of common stock at a price of $13.58 per share under the Kingsway America Inc. Employee Share Purchase Plan, which uses both employee and company matching contributions to buy shares on the open market.
After this transaction, Fitzgerald beneficially owns 1,459,718 shares of Kingsway common stock directly, plus 34,100 shares held in each of three separate trusts. The direct holdings disclosed include 400,000 shares of restricted stock that were granted on March 31, 2021. The filing characterizes this transaction as part of an ongoing employee share purchase program rather than a one‑time discretionary trade.
Kingsway Financial Services reported insider share transactions by its CFO and EVP, Kent A. Hansen. On 12/29/2025, he sold 7,500 shares of common stock at $13.6678 per share. On 12/30/2025, a total of 9,488 shares of common stock were surrendered at $12.83 per share to cover tax withholding upon vesting of restricted stock awards. After these transactions, Hansen beneficially owned 119,362 shares, which include restricted stock grants of 8,370 shares from December 15, 2022, 14,204 shares from March 26, 2024, and 20,728 shares from December 4, 2024, as well as remaining unvested restricted shares from 2024 grants.
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.