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 (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.
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.