Kingsway Finl SEC Filings

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.

Kingsway Financial Services Inc. (KFS) reported an insider share purchase by its President, CEO and Director, John Taylor Maloney Fitzgerald. On 11/28/2025 he acquired 192 shares of common stock at a price of $13.03 per share 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 matching contribution after 12 months of employment. Following this transaction, he beneficially owns 1,489,339 common shares directly and also holds 34,100 shares indirectly in each of several family trusts.

The shares were bought on the open market under the employee share plan. Contributions from both the employee and the company are used by the plan administrator to purchase Kingsway Financial Services Inc. shares on the open market through a registered stockbroker, and his holdings include 400,000 restricted shares that were granted on March 31, 2021.

Kingsway Financial Services Inc. officer Kent A. Hansen, who serves as CFO and EVP, reported a small open-market purchase of company stock. On 11/28/2025, he acquired 120 shares of common stock at a price of $13.03 per share, bringing his total beneficial ownership to 136,350 shares, held directly.

The filing explains that these shares were acquired under the Kingsway America Inc. Employee Share Purchase Plan. Under this plan, eligible employees can contribute up to 5% of adjusted salary, and after 12 months of employment the company matches 100% of the employee’s contribution, with both contributions used to buy Kingsway Financial Services Inc. shares on the open market. His total holdings include prior restricted stock grants made in December 2022, March 2024, and December 2024.

Kingsway Financial Services Inc. (KFS) filed a Form 4 reporting a routine employee share purchase by its CFO and EVP, Kent A. Hansen. On 11/17/2025, he acquired 123 shares of common stock at a price of $12.7 per share through the Kingsway America Inc. Employee Share Purchase Plan (ESPP). Following this transaction, he beneficially owned 136,230 common shares.

The ESPP allows eligible employees to contribute up to 5% of adjusted salary each pay period, with Kingsway America Inc. matching 100% of contributions for employees with at least 12 months of service, with all contributions used to buy Kingsway Financial Services Inc. shares on the open market. Hansen’s holdings include 8,370 restricted shares granted on December 15, 2022, 14,204 restricted shares granted on March 26, 2024, and 20,728 restricted shares granted on December 4, 2024.

Kingsway Financial Services Inc. (KFS)November 17, 2025 through a purchase coded “P” under the Kingsway America Inc. Employee Share Purchase Plan (ESPP) at $12.70 per share.

After this transaction, he beneficially owns 1,489,147 shares of common stock directly, plus 34,100 shares held in each of three separate trusts. The directly held amount includes 400,000 shares of restricted stock granted on March 31, 2021. Under the ESPP, eligible employees can contribute up to 5% of adjusted salary, and the company matches 100% of that contribution once a 12‑month service requirement is met.

Kingsway Financial Services Inc. (KFS) furnished its quarterly update. The company announced it issued a press release covering financial results for the three and nine months ended September 30, 2025. The release is furnished as Exhibit 99.1.

The disclosure is provided under Item 2.02, Results of Operations and Financial Condition, and is designated as “furnished” rather than “filed” under the Exchange Act. Kingsway’s common stock trades on the New York Stock Exchange under the symbol KFS.

Kingsway Financial Services (KFS) reported Q3 2025 results. Revenue reached $37.2 million, up from $27.1 million a year ago, reflecting growth across services. The quarter posted a net loss attributable to common shareholders of $2.8 million, similar to last year, with a basic and diluted loss per share of $0.10.

For the first nine months, revenue was $96.4 million versus $79.7 million, while the net loss attributable to common shareholders was $9.8 million compared with $7.7 million last year. Operating cash flow was essentially breakeven for the period, with $0.007 million provided; investing used $29.9 million, and financing provided $33.6 million.

Balance sheet and capital actions: Total assets were $235.1 million, up from $186.6 million at year-end. Bank loans were $55.8 million. Shareholders’ equity attributable to common shareholders improved to $16.6 million. The company issued preferred stock (650,000 outstanding; redemption amount $16.25 million) and increased common shares outstanding to 28,612,850. Kingsway acquired Roundhouse Electric & Equipment Co., Inc. on July 1, 2025 for approximately $23.5 million in cash and phantom equity awards.

Kingsway Financial Services (KFS): Greenhaven Road Investment Management, MVM Funds, two affiliated funds, and Scott Miller filed a Schedule 13G reporting beneficial ownership of 1,970,536 shares of common stock, equal to 6.8% of the class. The ownership figure includes 660,000 shares that may be acquired within 60 days under an option agreement with a third party.

The reporting persons report shared voting and dispositive power over 1,970,536 shares and no sole power. The percentage is based on 28,873,415 shares outstanding as of August 7, 2025. Within the group, Fund 1 reports 915,059 shares (3.2%) and Fund 2 reports 1,055,477 shares (3.7%). The certification states the securities were not acquired to change or influence control.