Item 3 is hereby amended and restated as follows: Pursuant to the Securities Exchange Agreement (as defined in Item 5), Mr. Eberwein purchased from the Issuer 287,631 shares (the "Purchased Shares") of Issuer Common Stock, at a purchase price per share of Common Stock of $10.43. In exchange for the Purchased Shares, Mr. Eberwein transferred 320,855 shares of Issuer 10.0% Series A Cumulative Perpetual Preferred Stock, par value $0.001 per share ("Preferred Stock") to the Company. The aggregate purchase price of the 1,033,069 Shares beneficially owned by Mr. Eberwein is approximately $21,426,901, excluding brokerage commissions. In addition to the 1,033,069 Shares, Mr. Eberwein owns 810,217 shares of the Issuer's 10% Series A Cumulative Perpetual Preferred Stock. The foregoing description of the Securities Exchange Agreement is qualified in its entirety by reference to the full text of the Securities Exchange Agreement, a copy of which is filed as Exhibit 99.2.

Items 5(a)-(c) are hereby amended and restated to read as follows: On December 8, 2025, Mr. Eberwein entered into a securities exchange agreement with the Issuer (the "Securities Exchange Agreement"), pursuant to which Mr. Eberwein purchased from the Issuer, 287,631 Purchased Shares of Issuer common stock at a purchase price per share of Common Stock of $10.43. In exchange for the Purchased Shares, Mr. Eberwein transferred 320,855 shares of Preferred Stock to the Issuer. The aggregate percentage of Shares reported owned by the Reporting Person is based upon 3,810,694 Shares, which is inclusive of 3,761,244 shares outstanding as of September 18, 2025 in addition to 49,450 Warrants attributed to the Reporting Person. The total number of Shares outstanding is based on information provided by the Issuer to the Reporting Person. The foregoing description of the Securities Exchange Agreement is qualified in its entirety by reference to the full text of the Securities Exchange Agreement, a copy of which is filed as Exhibit 99.2. As of the close of business on December 9, 2025, Mr. Eberwein beneficially owned 1,033,069 Shares. Percentage: 27.11%

1. Sole power to vote or direct vote: 1,033,069 2. Shared power to vote or direct vote: 0 3. Sole power to dispose or direct the disposition: 1,033,069 4. Shared power to dispose or direct the disposition: 0

Jeff Eberwein's transactions in the Shares in the last 60 days are set forth in Schedule A, attached hereto as Exhibit 99.1, and are incorporated herein by reference.

Exhibit 99.1 - Schedule A. Exhibit 99.2 - Securities Exchange Agreement, dated as of December 8, 2025, between Star Equity Holdings, Inc. and Jeffrey E. Eberwein.