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 insider transaction summary: The company’s President and CEO, John Taylor Maloney Fitzgerald, acquired 173 shares of Common Stock under transaction code P at $14.49 per share through the Kingsway America Inc. Employee Share Purchase Plan (ESPP). Following the purchase, his total reported beneficial ownership in common stock is 1,530,571 shares, which includes 400,000 shares of restricted stock granted in March 2021. The filing also discloses three indirect holdings of 20,000 shares each held in specified trusts. The ESPP permits employee contributions up to 5% of adjusted salary with a 100% company match after 12 months, and purchases are made on the open market by the plan administrator.
Kingsway Financial Services, Inc. (KFS) Form 4 summary: Joseph Stilwell and affiliated entities reported multiple sales of KFS common stock on 08/22/2025. Stilwell Activist Investments, L.P. sold 44,772 shares, Stilwell Activist Fund, L.P. sold 7,642 shares, and Stilwell Value Partners VII, L.P. sold 22,586 shares, each at $14.1784 per share. After the reported transactions, the reporting parties hold significant common stock positions: Joseph Stilwell directly holds 162,500 shares and beneficially holds additional shares through affiliated entities for totals shown on the form. The filing also discloses ownership of Class C and Class D preferred shares convertible into common stock at 2.63158 shares per preferred share, with redemption dates in 2032. The Form 4 is signed by Debra Rouse as attorney-in-fact for the reporting persons.
Kingsway Financial Services Inc. has filed a Form S-1 to register the resale of up to 1,419,001 shares of its common stock. These shares consist of 1,336,264 shares issued in a June 2025 private placement at $11.75 per share and 82,737 shares issued to the former owner of Bud’s Plumbing in exchange for cancelling a $1.25 million seller note. The filing allows the named selling stockholders to resell their shares from time to time on the market or in private transactions.
Kingsway will not sell any new shares in this offering and will not receive proceeds from stockholder resales. The company previously received approximately $15.7 million in gross proceeds from the 2025 private placement. Kingsway operates two main segments—Search Xcelerator and Extended Warranty—owning a portfolio of asset-light, recurring-revenue services businesses. As of the filing date, 28,873,415 common shares were issued and outstanding, alongside three series of convertible preferred stock with fixed 8% cumulative dividends.
Kingsway Financial Services, Inc. insider filing reports multiple August 18, 2025 sales by entities affiliated with Joseph Stilwell while retaining substantial ownership. The Form 4 shows aggregated dispositions of 71,429 common shares across Stilwell Activist Investments, L.P., Stilwell Activist Fund, L.P., and Stilwell Value Partners VII, L.P., at prices between $13.95 and $14.1631. After the transactions, certain affiliated entities and Mr. Stilwell continue to beneficially own large positions, including reported indirect holdings of 3,650,696, 701,904 (derivative-convertible basis noted), and other specified share counts. The filing also discloses convertible Class C and D preferred stakes convertible into common shares.
Kingsway Financial Services, Inc. (KFS) Schedule 13D/A (Forty-Seventh Amendment) reports that a Stilwell group of entities and Joseph Stilwell collectively beneficially own 5,788,271 shares, representing approximately 19.9% of common shares outstanding based on 28,873,415 shares plus conversion shares as of August 7, 2025. The filing states the Group's percentage decreased due to a change in the issuer's shares outstanding and that certain Group members sold shares since the prior amendment while others did not. Holdings reported include shares issuable on immediate conversion of Class C and Class D preferred stock (105,263 and 52,631 shares, respectively). The Group describes a history of activist positions and says its purpose was to seek profit from share appreciation through asserting shareholder rights and that it intends to gradually reduce its position over time.
John Taylor Maloney Fitzgerald, President & CEO and a director of Kingsway Financial Services, Inc. (KFS), reported an open-market purchase of 176 shares of the company's common stock on 08/18/2025 at a price of $14.16 per share. After this transaction he beneficially owns 1,530,398 shares directly. The filing also shows indirect ownership of 20,000 shares each through three trusts (Trust-GEF, Trust-LTF, Trust-MPF).
The shares purchased were acquired under the Kingsway America Inc. Employee Share Purchase Plan (ESPP), which matches eligible employee contributions. The filing notes that the total beneficial ownership includes 400,000 shares of restricted stock granted on March 31, 2021. The Form 4 was signed on behalf of the reporting person by an attorney-in-fact on 08/18/2025.
Kent A. Hansen, CFO & EVP of Kingsway Financial Services Inc. (KFS), reported an ESPP purchase on 08/18/2025. The filing shows an acquisition of 111 shares at $14.16 under the Kingsway America Inc. Employee Share Purchase Plan, which provides a company match for eligible employees. After the transaction the filing reports beneficial ownership of 135,575 shares, which includes previously granted restricted shares totaling 43,302 shares from 2022 and 2024 awards. The form was signed by an attorney-in-fact.