Kingsway Financial Services, Inc. Form 4 Filings

KINGSWAY Corp President and CEO John Taylor Maloney increased his stake through the company’s employee share plan. On May 29, he bought 250 shares of Common Stock in an open-market purchase at $10.03 per share under the Employee Share Purchase Plan.

After this transaction, his direct ownership rose to 1,455,634 Common shares, which includes 400,000 shares of restricted stock granted on March 31, 2021. He also reports indirect holdings of 29,100 shares of Common Stock in each of three family trusts labeled MPF, LTF, and GEF.

Kingsway Corp director-linked fund increases stake with open-market buys. Palm Global Small Cap Master Fund LP, an entity associated with director Joshua Horowitz, purchased 3,800 shares of Kingsway common stock on May 29, 2026 at $9.9105 per share and 700 shares on May 28, 2026 at $9.95 per share, for a total of 4,500 shares. After these trades, Palm Global indirectly holds 372,000 common shares, while Horowitz directly holds 32,500 shares. In addition, Palm Global holds Class D Preferred Stock that is convertible into 36,842.4 common shares at a $9.50 conversion price, with all such preferred shares to be redeemed for cash on May 8, 2032. The filing notes Palm Management (US) LLC and Horowitz may be deemed beneficial owners of Palm Global’s holdings but expressly disclaim beneficial ownership except to the extent of their pecuniary interest.

KINGSWAY Corp President and CEO John Taylor Maloney reported a bona fide charitable gift of 6,257 shares of common stock on May 27, 2026 at a value of $9.99 per share. After the gift, he directly holds 1,455,384 shares, including 400,000 restricted shares granted on March 31, 2021, and reports additional indirect holdings through three family trusts.

KINGSWAY Corp President and CEO Fitzgerald John Taylor Maloney reported an indirect open-market sale of 5,000 shares of Common Stock at $10.135 per share through a trust identified as Trust-MPF. After the sale, he reports 29,100 shares held indirectly in that trust and 1,461,641 shares held directly.

KINGSWAY Corp President and CEO John Taylor Maloney reported selling a total of 10,000 shares of common stock in open-market transactions through family trusts. The sales occurred on May 19 and May 20 at prices of about $10.30–$10.43 per share. After these transactions, he continues to hold 1,461,641 shares directly as of May 19, along with additional indirect holdings through trusts, so the sales represent a small portion of his overall position.

KINGSWAY Corp director Adam Jonathan Patinkin received a grant of 400,000 nonqualified stock options for Kingsway common stock. The options are split into 200,000 at an exercise price of $20 per share and 200,000 at $30 per share, all with a 10-year term.

According to the vesting schedule, 100,000 options at $20 vested on the grant date, another 100,000 at $20 vest on the first anniversary, 100,000 at $30 vest on the second anniversary, and the final 100,000 at $30 vest on the third anniversary, subject to his continued service.

Entities managed by David Capital Partners, LLC hold 1,524,000 and 1,023,000 Kingsway common shares, and 68,421.08 shares of Class D Preferred Stock that are convertible at a basis of 2.63158 common shares per preferred share and are redeemable by the company on May 8, 2032.

KINGSWAY Corp CFO & EVP Kent A. Hansen bought 144 shares of Common Stock on May 15, 2026 in an open‑market transaction at $10.85 per share. The shares were acquired through the company’s Employee Share Purchase Plan, which allows salary contributions and matching company contributions to buy stock. Following this purchase, Hansen directly owns 135,247 shares of Kingsway, including previously granted restricted stock awards.

KINGSWAY FINANCIAL SERVICES INC executive Kent A. Hansen, the company’s CFO and EVP, made an open-market purchase of 143 shares of common stock at $10.93 per share on April 30, 2026. The shares were acquired through the company’s Employee Share Purchase Plan, which matches eligible employee contributions.

Following this transaction, Hansen directly holds 135,103 common shares, a figure that includes 6,909 restricted shares granted on December 4, 2024 and 14,568 restricted shares granted on March 17, 2026.

Kingsway Financial Services Inc. President and CEO John Taylor Maloney increased his direct stake through the company’s employee share purchase plan. On April 30, 2026, he purchased 229 shares of common stock at $10.93 per share, bringing his directly held common shares to 1,461,411, which includes 400,000 restricted shares granted on March 31, 2021. The filing also reports indirect holdings of 34,100 shares of common stock in each of three trusts identified as Trust-MPF, Trust-LTF, and Trust-GEF.

KINGSWAY FINANCIAL SERVICES INC President and CEO Fitzgerald John Taylor Maloney bought 211 shares of Common Stock on April 15, 2026 at $11.85 per share. The shares were acquired through the company’s Employee Share Purchase Plan, which uses employee contributions and matching company contributions to buy stock on the open market.

After this purchase, he directly holds 1,461,182 Common shares, which include 400,000 shares of restricted stock granted on March 31, 2021. He also has indirect ownership of 34,100 shares in each of three separate trusts identified as Trust-GEF, Trust-LTF, and Trust-MPF.

Hansen Kent A reported acquisition or exercise transactions in this Form 4 filing.

Kingsway Financial Services CFO & EVP Kent A. Hansen received a grant of 14,568 shares of common stock on March 17, 2026 at a reference price of $11.02 per share. The restricted stock award, granted under the 2020 Equity Incentive Plan, vests ratably over three years starting on December 1, 2026. After this award, Hansen directly holds 134,675 shares, including earlier restricted stock grants of 7,102 shares from March 26, 2024 and 13,818 shares from December 4, 2024.

Kingsway Financial Services Inc. executive Kent A. Hansen, the CFO and EVP, bought 153 shares of common stock at $10.22 per share in an open-market purchase. This increased his directly held position to 120,260 common shares, including previously granted restricted stock awards.

The filing explains that these shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan (ESPP). 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 to buy shares on the open market.

KINGSWAY FINANCIAL SERVICES INC President and CEO John Taylor Maloney bought 244 shares of common stock at $10.22 per share in an open-market purchase made through the company’s Employee Share Purchase Plan. After this transaction, he directly owns 1,460,971 common shares.

The direct holdings figure includes 400,000 shares of restricted stock granted on March 31, 2021. In addition, Form 4 entries show 34,100 shares of common stock held indirectly in each of three trusts identified as Trust-GEF, Trust-LTF, and Trust-MPF.

Kingsway Financial Services Inc. President and CEO John Taylor Maloney bought 234 shares of common stock on March 13, 2026 in an open-market purchase at $10.71 per share. This increased his directly held stake to 1,460,727 common shares, which includes 400,000 shares of restricted stock granted on March 31, 2021.

The filing also shows indirect ownership of 34,100 common shares in each of three separate trusts identified as Trust-GEF, Trust-LTF, and Trust-MPF. The newly acquired shares were purchased through the Kingsway America Inc. Employee Share Purchase Plan, where employee payroll contributions are matched by the company and used to buy shares on the open market.

Kingsway Financial Services Inc. Chief Financial Officer and Executive Vice President Kent A. Hansen reported a small open-market purchase of company stock through an employee share purchase plan. On March 13, he acquired 146 shares of common stock at $10.71 per share. Following this transaction, he directly holds 120,107 common shares, which the footnotes indicate include previously granted restricted stock awards.

Kingsway Financial Services executive Kent A. Hansen, the CFO and EVP, bought 126 shares of common stock in an open-market purchase at $12.34 per share. The shares were acquired through the company’s Employee Share Purchase Plan, bringing his directly held stake to 119,961 shares.

Kingsway Financial Services Inc. president and CEO John Taylor Maloney bought 202 shares of common stock on February 27, 2026 in an open-market purchase at $12.34 per share. The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan, which matches eligible employee contributions in company stock.

After this transaction, Maloney directly owns 1,460,493 common shares, including 400,000 shares of restricted stock granted on March 31, 2021. In addition, 34,100 common shares are held indirectly in each of three trusts identified as Trust-GEF, Trust-LTF and Trust-MPF.

Kingsway Financial Services Inc. Chief Financial Officer and Executive Vice President Kent A. Hansen bought 128 shares of common stock in an open-market purchase at $12.19 per share. Following this transaction, he directly owns 119,835 common shares, which include 7,102 restricted shares granted on March 26, 2024 and 13,818 restricted shares granted on December 4, 2024.

Kingsway Financial Services President and CEO John Taylor Maloney reported an open-market purchase of 205 shares of common stock at $12.19 per share. The shares were acquired through the company’s Employee Share Purchase Plan, which matches eligible employee contributions.

After this transaction, Maloney directly owned 1,460,291 common shares, which includes 400,000 shares of restricted stock granted on March 31, 2021. He also reported indirect ownership of 34,100 shares in each of three separate trusts identified as Trust‑GEF, Trust‑LTF, and Trust‑MPF.

Kingsway Financial Services Inc. President and CEO John Taylor Maloney Fitzgerald reported a small open-market purchase of 183 shares of Common Stock on February 2, 2026 at $13.69 per share. The shares were acquired through the company’s Employee Share Purchase Plan, which allows eligible employees to contribute up to 5% of adjusted salary with a 100% company match after 12 months of employment.

Following this transaction, Fitzgerald directly beneficially owns 1,460,086 Common shares, which includes 400,000 restricted shares granted on March 31, 2021. He also has indirect beneficial ownership of 34,100 shares in each of three trusts labeled Trust-GEF, Trust-LTF, and Trust-MPF.

Kingsway Financial Services Inc. executive transaction: CFO & EVP Kent A. Hansen acquired 114 shares of Kingsway common stock on February 2, 2026 at a price of $13.69 per share.

The purchase was made through the Kingsway America Inc. Employee Share Purchase Plan, where eligible employees contribute up to 5% of adjusted salary and, after 12 months of employment, receive a 100% company matching contribution. Following this transaction, Hansen beneficially owned 119,707 common shares, including restricted stock grants of 7,102 shares from March 26, 2024 and 13,818 shares from December 4, 2024.

Kingsway Financial Services Inc. President and CEO Fitzgerald John Taylor Maloney reported a small open‑market purchase of company stock. On January 15, 2026, he acquired 185 shares of Common Stock at $13.54 per share through the Kingsway America Inc. Employee Share Purchase Plan.

Following this transaction, he directly beneficially owns 1,459,903 Common shares, which include 400,000 restricted shares granted on March 31, 2021. He also reports indirect ownership of 34,100 shares in each of three separate trusts (Trust‑GEF, Trust‑LTF, and Trust‑MPF).

Kingsway Financial Services Inc. executive Kent A. Hansen, the company’s CFO and EVP, purchased 116 shares of common stock on January 15, 2026 at $13.54 per share. The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan, which uses employee and company matching contributions to buy stock on the open market.

After this transaction, Hansen beneficially owns 119,593 common shares directly, including 7,102 restricted shares granted on March 26, 2024 and 13,818 restricted shares granted on December 4, 2024.

Kingsway Financial Services Inc. insider trading report shows the company’s Chief Financial Officer and Executive Vice President, Kent A. Hansen, acquired additional common shares on 12/31/2025. The filing reports a purchase of 115 shares of Kingsway common stock at a price of $13.58 per share, bringing his total directly held beneficial ownership to 119,477 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 the company matching 100% of contributions for employees with at least 12 months of service. The filing notes that this ownership total includes 7,102 restricted shares granted on March 26, 2024 and 13,818 restricted shares granted on December 4, 2024.

Kingsway Financial Services Inc. President and CEO John Taylor Maloney Fitzgerald reported a small open‑market acquisition of company stock through an employee plan. On 12/31/2025, he acquired 184 shares of common stock at a price of $13.58 per share under the Kingsway America Inc. Employee Share Purchase Plan, which uses both employee and company matching contributions to buy shares on the open market.

After this transaction, Fitzgerald beneficially owns 1,459,718 shares of Kingsway common stock directly, plus 34,100 shares held in each of three separate trusts. The direct holdings disclosed include 400,000 shares of restricted stock that were granted on March 31, 2021. The filing characterizes this transaction as part of an ongoing employee share purchase program rather than a one‑time discretionary trade.

Kingsway Financial Services reported insider share transactions by its CFO and EVP, Kent A. Hansen. On 12/29/2025, he sold 7,500 shares of common stock at $13.6678 per share. On 12/30/2025, a total of 9,488 shares of common stock were surrendered at $12.83 per share to cover tax withholding upon vesting of restricted stock awards. After these transactions, Hansen beneficially owned 119,362 shares, which include restricted stock grants of 8,370 shares from December 15, 2022, 14,204 shares from March 26, 2024, and 20,728 shares from December 4, 2024, as well as remaining unvested restricted shares from 2024 grants.

Kingsway Financial Services Inc. reported an insider share sale by its President and CEO, John Taylor Maloney Fitzgerald, who is also a director. On 12/23/2025, he sold 30,000 shares of Kingsway common stock in an open market transaction coded as a sale at a price of $13.3238 per share.

After this transaction, he beneficially owned 1,459,534 shares directly, which include 400,000 shares of restricted stock granted on March 31, 2021. He also had indirect beneficial ownership of additional shares through trusts, including 34,100 shares held in each of three trusts identified as Trust‑GEF, Trust‑LTF, and Trust‑MPF.

Kingsway Financial Services Inc. insider Joseph Stilwell, a director and 10% owner, reported a sale of Common Stock. On 12/22/2025, Stilwell Associates, L.P. sold 19,229 shares of Kingsway common stock at $12.80 per share.

After this transaction, Stilwell reports 162,500 shares owned directly and additional indirect holdings of Kingsway common stock through several investment entities, including 300,000, 2,254,971, 436,911 and 371,568 shares. He also reports indirect interests in Kingsway preferred stock: Class D and Class C series with stated value of $25 per share, convertible into common stock at 2.63158 common shares per preferred share, with underlying amounts of 52,631, 88,421 and 16,842 common shares and redemption dates in 2032 as disclosed.

Kingsway Financial Services Inc. insider Joseph Stilwell and affiliated funds reported option-related share transactions. On December 17, 2025, entities associated with Stilwell, a director and 10% owner, reported dispositions of Kingsway common stock at a price of $8.25 per share through stock options described as an obligation to sell.

Footnotes explain that on March 31, 2025, Stilwell Value LLC entered into three option agreements granting buyers options to purchase 815,000, 660,000, and 275,000 Kingsway common shares, each at an exercise price of $8.25, later amended on December 17, 2025 to be exercisable at any time before 5:00 p.m. Eastern on December 29, 2025. The filing also notes indirect ownership of Kingsway shares and preferred stock (Class C and D) by several Stilwell-managed limited partnerships, with those preferred shares convertible into common stock at a stated conversion basis of 2.63158 common shares per preferred share.

Oakmont Capital Inc., a 10% owner and director-level affiliate of Kingsway Financial Services Inc. (KFS), reported a transaction involving 500,000 shares of Kingsway common stock. On December 17, 2025, Oakmont entered into a stock option (an obligation to sell) covering 500,000 common shares at a price of $8.25 per share, pursuant to an Option Agreement with David Capital Partners Special Situation Fund, LP that is exercisable up to 5:00 p.m. Eastern Time on December 29, 2025. After this reported transaction, Oakmont directly beneficially owns 1,987,830 shares of common stock. Oakmont also holds Class B and Class C Preferred Stock that are each convertible into common stock at a rate of 2.63158 common shares per preferred share, with all Class B Preferred Stock subject to redemption on September 24, 2031 and all Class C Preferred Stock subject to redemption on February 12, 2032.

Oakmont Capital Inc., a director-level holder of Kingsway Financial Services Inc. (KFS), reported an indirect sale-related transaction involving 500,000 common shares at $8.25 per share on December 17, 2025. The filing shows these shares as disposed of and reflects that 1,987,830 common shares are now indirectly held through Oakmont, with an additional 34,750 common shares held indirectly through a retirement plan.

The report also details derivative securities held indirectly by Oakmont. These include Class B Preferred Stock convertible into 210,526.4 common shares, redeemable by the company on September 24, 2031, and Class C Preferred Stock convertible into 105,263.2 common shares, redeemable on February 12, 2032. A stock option representing an obligation to sell 500,000 common shares at $8.25, linked to an option agreement with David Capital Partners Special Situation Fund, LP, is shown with zero derivative securities remaining after the reported transaction.

Oakmont Capital Inc., a director of Kingsway Financial Services Inc. (KFS), reported a significant change in its holdings of the company’s common stock. On December 17, 2025, Oakmont disposed of 500,000 shares of common stock at $8.25 per share through a stock option arrangement and reported indirect ownership of 1,987,830 common shares afterward, held through Oakmont.

Oakmont also reports additional indirect holdings of common stock through a retirement plan, spouse, and a trust. Beyond common shares, Oakmont holds Class B Preferred Stock with a stated value of $25 per share, convertible into 2.63158 common shares per preferred share and redeemable on September 24, 2031, and Class C Preferred Stock with the same conversion terms, redeemable on February 12, 2032.

The transaction stems from an option agreement with David Capital Partners Special Situation Fund, LP, originally dated March 31, 2025 and amended on December 17, 2025 so the option to purchase the 500,000 common shares at $8.25 can be exercised at any time before 5:00 p.m. Eastern Time on December 29, 2025.

Kingsway Financial Services Inc. reported that its CFO and EVP, Kent A. Hansen, acquired additional common shares through the company’s employee share purchase plan. On 12/16/2025, he bought 122 shares of common stock at $12.82 per share in an open-market purchase coded as an acquisition. Following this transaction, he beneficially owns 136,472 common shares.

The shares were acquired under 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 of employment, and those contributions are used to buy Kingsway shares on the open market. His total 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. 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.

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. 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. 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) President and CEO John Taylor Maloney Fitzgerald reported acquiring 197 shares of common stock on 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 (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.