KINGSWAY Corp (KWY) SEC Filings

KINGSWAY Corp (KWY) director and President & CEO John Taylor Maloney purchased 239 shares of Common Stock on August 31, 2026 at $10.45 per share, through the Kingsway America Inc. Employee Share Purchase Plan. Following this purchase, his direct holdings total 1,426,907 shares, including 300,000 restricted shares granted on March 31, 2021. The filing also reports three indirect holdings of 29,100 shares each in separate trusts.

KINGSWAY Corp (KWY) director Joshua Horowitz reported indirect open-market purchases of Common Stock through Palm Global Small Cap Master Fund LP on August 18–20, 2026, totaling 9,103 shares at weighted-average prices around $9.75–$9.89 per share. Horowitz also reports 32,500 Common shares held directly and an indirect derivative position in Class D Preferred Stock convertible into 36,842.4 Common shares at a $9.50 conversion price. Palm Management (US) LLC and Horowitz may be deemed beneficial owners of Palm Global’s holdings but each disclaims beneficial ownership except to the extent of pecuniary interest.

KINGSWAY Corp (KWY) reported that President and CEO Fitzgerald John Taylor Maloney purchased 254 shares of common stock on August 17, 2026 at $9.87 per share. The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan, which allows up to 5% of adjusted salary to be contributed with a 100% company match after 12 months of employment. Following this ESPP purchase, he directly owns 1,426,668 shares, including 300,000 restricted shares granted on March 31, 2021, and also reports indirect ownership of 29,100 shares in each of three separate trusts.

KINGSWAY Corp (KWY) executive Kent A. Hansen, CFO & EVP, purchased 158 shares of common stock on 2026-08-17 at $9.87 per share. The shares were acquired through the Kingsway America Inc. Employee Share Purchase Plan, under which eligible employees can contribute up to 5% of adjusted salary with a 100% company match. Following this transaction, Hansen directly holds 136,195 shares of common stock, including 6,909 restricted shares granted on December 4, 2024 and 14,568 restricted shares granted on March 17, 2026.

KINGSWAY Corp (KWY) insider group led by Joseph Stilwell reported sales of 100,000 shares of Common Stock on August 13, 2026 at $10.00 per share, executed indirectly through Stilwell Associates, L.P., Stilwell Activist Investments, L.P., and Stilwell Value Partners VII, L.P. Joseph Stilwell continues to hold 162,500 Common shares directly and has additional indirect positions in Class C and Class D Preferred Stock that are convertible into Common Stock at $9.50 per share, with conversions based on 2.63158 Common shares per preferred share and mandatory redemption dates in 2032. Footnotes state that these partnership-held shares are owned directly by the respective funds and only indirectly by Stilwell through control of their general partner, and he disclaims beneficial ownership beyond his pecuniary interest.

Kingsway Corporation reported strong results for the three and six months ended June 30, 2026. Second-quarter revenue grew 28% to $39.4 million, with KSX segment revenue up 68% to $22.3 million and Extended Warranty revenue of $17.1 million.

KSX generated a segment quarterly record of $4.3 million in adjusted EBITDA, while Extended Warranty delivered adjusted EBITDA of $1.1 million and lender-defined Modified Cash adjusted EBITDA of $2.9 million. Consolidated non-GAAP adjusted EBITDA for the quarter was $5,178 (in thousands), compared with $1,653 (in thousands) a year earlier, and GAAP net income for the quarter was $157 (in thousands). Management reaffirmed its 2026 targets of completing three to five acquisitions and achieving double-digit organic growth in both segments.

Kingsway Corporation, a Delaware holding company that owns asset-light B2B and B2C services businesses, reported stronger operating results for the quarter ended June 30, 2026. Revenue was $39.4 million, compared with $30.9 million a year earlier, and net income was $0.2 million versus a net loss of $3.2 million. However, after preferred dividends, net loss attributable to common shareholders was $0.9 million, compared with a $3.6 million loss in the prior-year quarter.

For the first six months of 2026, revenue was $78.4 million versus $59.3 million in 2025, and net loss attributable to common shareholders was $3.7 million versus $7.1 million. Operating cash flow was $1.2 million, with total cash and restricted cash of $15.0 million and total debt of $69.6 million.

Kingsway completed the sale of its Trinity Warranty Solutions subsidiary on May 8, 2026 for $8.0 million in gross consideration, recording a $1.3 million gain. Goodwill totaled $65.4 million after a small acquisition and measurement-period adjustments, while trade-name intangible impairments were $0.5 million year-to-date. The company disclosed covenant violations and waivers on several subsidiary loans (SNS, DDI, KPH), reclassifying related debt to current and noting potential acceleration risk if future covenant compliance is not maintained.

Kent A. Hansen, CFO & EVP of Kingsway Corp, purchased 174 shares of Common Stock at $8.98 per share on July 30, 2026 through the Kingsway America Inc. Employee Share Purchase Plan. Under this ESPP, eligible employees may contribute up to 5% of adjusted salary with a 100% company match after 12 months to buy shares on the open market. Following this purchase, Hansen directly owns 136,037 shares, including 6,909 restricted shares granted on December 4, 2024 and 14,568 restricted shares granted on March 17, 2026.

Kingsway Corp President and CEO Fitzgerald John Taylor Maloney purchased 278 shares of Common Stock on July 30, 2026 at $8.98 per share through the company’s Employee Share Purchase Plan. Following this purchase, he directly holds 1,426,414 shares, including 300,000 shares of restricted stock granted March 31, 2021, and also reports indirect holdings of 29,100 shares in each of three trusts.