Fitzgerald John Taylor Maloney 4

What Happened
John Taylor Maloney, President & CEO and a director of Kingsway Financial Services Inc. (KFS), acquired 183 shares on 2026-02-02 at $13.69 per share, for a total purchase of $2,505. The shares were purchased under the company’s Employee Share Purchase Plan (ESPP). This was a purchase (not a sale), though the amount is modest and appears to be a routine ESPP acquisition rather than a large directional trade.

Key Details

• Transaction date: 2026-02-02; Transaction code: P (purchase).
• Price: $13.69 per share; Shares acquired: 183; Total value: $2,505 (approx.).
• Shares were acquired pursuant to the Kingsway America Inc. ESPP; purchases are made on the open market by the plan administrator through a broker (footnote F1).
• Filing date / Period of report: 2026-02-02 — filing appears timely (no late-filing indication).
• Filing notes inclusion of 400,000 restricted shares granted March 31, 2021 (footnote F2). The filing excerpt does not state total shares owned by Maloney after this purchase.

Context

• ESPP purchases are employee benefit transactions: employees contribute (up to 5% of adjusted salary) and, after 12 months of service, the company may match contributions (100% match under this ESPP). The plan administrator then acquires shares on the open market for participants.
• Small purchases through ESPPs are common and often routine; while purchases can be viewed as a mild positive signal, they do not necessarily indicate a significant change in insider sentiment.