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.
David Capital Partners and affiliates report a significant stake in Kingsway Financial Services Inc. They disclose beneficial ownership of 2,615,421.08 shares of common stock, representing approximately 9.0% of Kingsway’s outstanding common shares, including 68,421.08 shares that may be acquired by converting Class D Preferred Stock.
The filing explains that David Capital Partners Fund, LP and David Capital Partners Special Situation Fund, LP exercised amended option agreements on December 17, 2025 to buy, respectively, 275,000 and 1,040,000 shares of Kingsway common stock at an exercise price of $8.25 per share. DCP Special also holds Class D Preferred Stock, which is convertible into common stock at an initial conversion price of $9.50 per share. The reporting persons state that the position is held for investment purposes and that they may buy or sell additional shares, or use hedging and derivative strategies, depending on market and company conditions.
Kingsway Financial Services Inc. insider John Taylor Maloney Fitzgerald, who serves as President, CEO and Director, reported acquiring additional common shares. On 12/16/2025 he acquired 195 shares of common stock at a price of $12.82 per share, increasing his directly held position to 1,489,534 common shares.
He also reports indirect ownership of 34,100 common shares in each of three separate trusts (Trust-GEF, Trust-LTF and Trust-MPF. According to the notes, the acquired shares were purchased under the Kingsway America Inc. Employee Share Purchase Plan, under which eligible employees can contribute up to 5% of adjusted salary and receive a 100% company match after 12 months of employment. The filing states that the total direct holdings include 400,000 shares of restricted stock granted on March 31, 2021.
Kingsway Financial Services director Adam Jonathan Patinkin reported indirect acquisitions of the company’s common stock through investment funds he manages. On December 17, 2025, David Capital Partners Fund, LP exercised options to acquire 275,000 shares at $8.25 per share, and David Capital Partners Special Situation Fund, LP exercised options to acquire an additional 540,000 and 500,000 shares at the same price. The funds also hold 26,000 shares of Class D Preferred Stock, each convertible into 2.63158 common shares, with all outstanding Class D Preferred Stock scheduled to be redeemed by Kingsway on May 8, 2032.
Palm Global Small Cap Master Fund LP, Palm Management (US) LLC, Bradley C. Palmer and Joshua S. Horowitz report beneficial ownership of 436,842.4 Kingsway Financial common shares, about 1.5% of the 28,956,152 shares outstanding as of November 6, 2025. Their holdings include 36,842.4 shares that may be obtained by converting Class D Preferred Stock at an initial price of $9.50 per share, or 2.6316 common shares per preferred share.
On March 31, 2025 they entered option agreements to buy up to 1,750,000 shares at $8.25. After a December 17, 2025 amendment allowing early exercise, Palm Global bought 252,500 shares and Mr. Horowitz bought 22,500 shares. The exercise cost was $2,083,125 for Palm Global (from working capital) and $185,625 for Mr. Horowitz (from personal funds). The group states the investment is for investment purposes but may buy or sell more stock, use hedging or short selling, and engage with the company’s board and other stockholders.
Kingsway Financial Services Inc. director Joshua Horowitz reported exercising options on 12/17/2025 to acquire 22,500 shares of common stock at $8.25 per share, increasing his direct holdings to 32,500 common shares.
On the same date, Palm Global Small Cap Master Fund LP acquired 252,500 common shares at $8.25, resulting in 367,500 common shares reported as indirectly owned, with Palm Management (US) LLC and Mr. Horowitz stating they may be deemed beneficial owners through Palm Global but expressly disclaiming beneficial ownership beyond their pecuniary interest. Palm Global also holds 14,000 shares of Class D Preferred Stock, each with a stated value of $25 and initially convertible into 2.6316 common shares at a conversion price of $9.50 per share, with all then-outstanding Class D Preferred Stock to be redeemed for cash on May 8, 2032.
Kingsway Financial Services Inc. received an updated ownership disclosure from a shareholder group led by Oakmont Capital Inc. In an option agreement exercised on December 17, 2025, Oakmont sold 500,000 Kingsway common shares to David Capital Partners Special Situation Fund, LP at US$8.25 per share.
After this transaction, the group comprising Oakmont, E.J.K. Holdings Inc., 1272562 Ontario Inc., Terence M. Kavanagh and Gregory P. Hannon is reported to beneficially own 2,386,119 shares, or about 8.24% of Kingsway’s outstanding common stock as of that date. This percentage is based on 28,956,152 shares outstanding as of November 6, 2025, plus 315,789 shares issuable upon exercise of the group’s Series B warrants and conversion of its Class C preferred shares.
Kingsway Financial Services Inc. director and 10% owner Joseph Stilwell, together with affiliated fund Stilwell Associates, L.P., reported sales of Kingsway common stock on December 15 and 16, 2025. Associates sold 34,269 shares at $12.8005 on December 15 and 10,429 shares at $12.80 on December 16.
After these trades, the report shows Stilwell directly owning 162,500 Kingsway common shares and indirect interests in several large positions, including 545,135 shares held by Stilwell Associates, 3,550,382 shares held by Stilwell Activist Investments, L.P., 457,181 shares held by Stilwell Activist Fund, L.P., and 590,410 shares held by Stilwell Value Partners VII, L.P. He reports these as indirectly owned through his role at Stilwell Value LLC and disclaims beneficial ownership beyond his pecuniary interest.
The filing also lists indirect holdings of 20,000 shares of Class D Preferred Stock and 33,600 and 6,400 shares of Class C Preferred Stock. The Class C and Class D Preferred Stock each have a stated value of $25 per share and are convertible at any time into Kingsway common stock at a conversion basis of 2.63158 common shares per preferred share, with all outstanding Class D Preferred Stock to be redeemed on May 7, 2032 and all outstanding Class C Preferred Stock to be redeemed on February 12, 2032.
Kingsway Financial Services Inc is the focus of an ownership update from a shareholder group led by Joseph Stilwell. The group reports beneficial ownership of 5,463,502 common shares, including shares underlying Class C and Class D preferred stock, representing about 18.8% of the company’s common shares, based on 28,956,152 shares outstanding as of November 6, 2025 plus the convertible preferred.
The group states that a member has sold common shares and that, having achieved its objective of profiting by asserting shareholder rights, it now intends to gradually reduce its position over time, while still allowing for additional purchases or sales. Existing arrangements include Class C and Class D preferred stock with a stated value of $25 per share, each convertible into 2.63158 common shares, and option agreements giving third-party buyers the right to purchase blocks of common stock at an exercise price of $8.25 per share on December 29, 2025.
Kingsway Financial Services Inc. director and 10% owner Joseph Stilwell reported an insider transaction involving the sale of 67,500 shares of common stock at $12.80 per share on December 11, 2025 through Stilwell Associates, L.P. After this sale, Stilwell-related entities continue to hold significant positions, including 579,404 common shares via Stilwell Associates, 3,550,382 shares via Stilwell Activist Investments, 457,181 shares via Stilwell Activist Fund, and 590,410 shares via Stilwell Value Partners VII, along with shares held directly by Stilwell.
The filing also lists preferred stock holdings that can convert into common stock. Class D Preferred Stock with a stated value of $25 per share is convertible into 52,631 common shares and is scheduled to be redeemed by Kingsway on May 7, 2032. Class C Preferred Stock, also with a stated value of $25 per share, is convertible into 88,421 and 16,842 common shares across two positions and is scheduled to be redeemed on February 12, 2032.
Kingsway Financial Services Inc. insider activity: Director and 10% owner Joseph Stilwell, reporting jointly with several Stilwell investment partnerships, disclosed open-market sales of a total of 55,000 shares of Kingsway common stock. Stilwell Associates, L.P. sold 35,000 shares on December 8, 2025 at $12.82 per share and 20,000 shares on December 9, 2025 at $12.80 per share.
Following these trades, Stilwell Associates reports indirect beneficial ownership of 646,904 common shares, while other Stilwell entities report additional indirect holdings of 3,550,382, 457,181 and 590,410 common shares. The group also reports Class C and Class D preferred stock that is convertible into common stock at 2.63158 common shares per preferred share, with all outstanding Class D preferred to be redeemed on May 7, 2032 and all outstanding Class C preferred to be redeemed on February 12, 2032. Stilwell disclaims beneficial ownership of indirectly held shares except to the extent of his pecuniary interest.