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 (KFS) reported an insider transaction by its CFO & EVP. On 10/30/2025, the officer acquired 111 shares of common stock at $14.08 per share. Following the purchase, direct beneficial ownership totaled 136,107 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 a 100% company match after 12 months, with shares bought on the open market. Holdings include restricted stock grants of 8,370 (12/15/2022), 14,204 (03/26/2024), and 20,728 (12/04/2024).
Kingsway Financial Services (KFS) reported an insider purchase by its Director and President & CEO. On 10/30/2025, the reporting person bought 177 shares of common stock at $14.08 (transaction code P). The filing notes these shares were acquired under the company’s Employee Share Purchase Plan, which allows employee contributions with a company match and open‑market purchases by the plan administrator.
Following the transaction, the reporting person directly beneficially owns 1,488,950 shares. Additional indirect holdings are reported, including 34,100 shares held in each of Trust‑GEF, Trust‑LTF, and Trust‑MPF. The ownership also includes 400,000 shares of restricted stock granted on March 31, 2021.
Kingsway Financial Services (KFS) reported an insider transaction by CFO & EVP Kent A. Hansen. On 10/15/2025, he purchased 98 shares of Common Stock at $15.92 per share, recorded as an open-market buy via the Kingsway America Inc. Employee Share Purchase Plan (ESPP). After this trade, his beneficial ownership stood at 135,996 shares.
The ESPP permits eligible employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months, with purchases made on the open market. Disclosed holdings include restricted stock grants of 8,370 (12/15/2022), 14,204 (3/26/2024), and 20,728 (12/4/2024) shares.
Kingsway Financial Services (KFS) disclosed an insider transaction: President and CEO, and Director, John Taylor Maloney Fitzgerald acquired 157 shares of common stock on 10/15/2025 at $15.92 per share through the company’s Employee Share Purchase Plan. Following the trade, he beneficially owned 1,488,773 shares directly, and 34,100 shares each held indirectly via Trust‑GEF, Trust‑LTF, and Trust‑MPF. The holdings include 400,000 shares of restricted stock granted on March 31, 2021.
John Taylor Maloney, President and CEO and a director of Kingsway Financial Services Inc. (KFS), reported transactions dated 09/26/2025 on a Form 4. The filing shows repeated entries of 14,100-share movements coded J(1) at a price of $14.57 involving transfers between the reporting person’s direct holdings and three trusts (GEF, LTF, MPF). The filing states the reporting person transferred shares to trusts for which he serves as trustee but retained voting and investment power, so his beneficial ownership did not change. The report notes total direct beneficial holdings in the ranges shown: approximately 1,516,645, 1,502,545, and 1,488,445 shares after specific transactions, and discloses inclusion of 400,000 restricted shares granted on 03/31/2021. The Form 4 was signed by an attorney-in-fact, Debra Rouse, on 09/30/2025.
Joseph Stilwell and affiliated entities reported insider sales of Kingsway Financial Services Inc. (KFS) common stock on September 16-17, 2025. The Form 4 shows aggregate sales by three affiliated investment vehicles of 68,000 common shares: 20,000 shares sold on 09/16/2025 at $14.40 and 48,000 shares sold on 09/17/2025 at $14.47. After these transactions certain indirect holdings remain large, with the largest reported indirect position totaling 3,550,382 shares following the 09/17 trades and other indirect holdings reported at 457,181, 590,410 and 701,904 through affiliated entities. The filing also discloses convertible Class C and Class D preferred stakes that convert into common shares (conversion rate 2.63158) and remaining derivative common equivalents reported as 52,631 and 88,421/16,842 across certain preferred positions. The Form 4 is signed by an attorney-in-fact on behalf of Stilwell and his affiliated entities.
John Taylor Maloney Fitzgerald, President & CEO and Director of Kingsway Financial Services Inc. (KFS), acquired 174 shares of KFS common stock on 09/15/2025 at $14.36 per share under the company's Employee Share Purchase Plan (ESPP). The ESPP allows employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months; purchases are executed on the open market by the plan administrator. After the transaction, Mr. Fitzgerald beneficially owns 1,530,745 shares, which includes 400,000 shares of restricted stock granted on March 31, 2021. The Form 4 was signed by an attorney-in-fact on behalf of Mr. Fitzgerald on 09/16/2025.
Kent A. Hansen, Chief Financial Officer and Executive Vice President of Kingsway Financial Services Inc. (KFS), purchased shares under the company's Employee Share Purchase Plan on 09/15/2025. The filing shows a purchase (code P) at $14.36 per share for 109 shares acquired through the ESPP administrator. Following the transaction, Mr. Hansen beneficially owns 135,791 shares, which includes restricted stock grants of 8,370, 14,204, and 20,728 shares from 2022, March 2024 and December 2024 respectively. The ESPP permits eligible employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months of service; shares are purchased on the open market by the plan administrator.
Kingsway Financial Services Inc. insider sale disclosure: This Form 4 shows that on September 8, 2025 multiple Stilwell-related entities sold common stock of KFS at $14.41 per share. Stilwell Activist Investments, L.P. sold 14,944 shares, Stilwell Activist Fund, L.P. sold 2,551 shares, and Stilwell Value Partners VII, L.P. sold 7,505 shares. Joseph Stilwell is identified as a director and >10% owner and directly owns 162,500 common shares. Several Stilwell entities and affiliates report substantial indirect holdings, including reported beneficial ownership figures of 3,590,980, 464,342, 610,651, and 701,904 common shares. The filing also discloses convertible Class D and Class C preferred shares with stated value $25 and conversion ratio 2.63158 common shares per preferred share, and redemption dates in 2032.
Kent A. Hansen, Chief Financial Officer and EVP of Kingsway Financial Services Inc. (KFS), purchased shares under the company's Employee Share Purchase Plan (ESPP). On 08/29/2025 Mr. Hansen acquired 107 shares of KFS common stock at $14.49 per share through the ESPP. After the purchase he beneficially owns 135,682 shares, which includes restricted stock grants of 8,370, 14,204, and 20,728 shares granted on December 15, 2022, March 26, 2024, and December 4, 2024, respectively. The ESPP permits eligible employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months of employment; shares are bought on the open market by the plan administrator. The Form 4 was signed by an attorney-in-fact for Mr. Hansen on 09/02/2025.