Star Equity Holdings, Inc.

Item 1.01. Entry into a Material Definitive Agreement. Stock Purchase Agreement On October 23, 2026 (the “Closing Date”), Star Equity Holdings, Inc. (the “Company”) entered into a Stock Purchase Agreement (the “Purchase Agreement”) with PD Machine, LLC (the “Target Company”); Davis Rentals, LLC (the “Real Estate Target Company”); the Company’s indirect wholly owned subsidiaries: Alliance Machine Solutions, Inc. (“Alliance Machines”) and 1218 East 135 South, Inc. (“New Real Estate Sub”); Phil's Welding, Inc. (the “Target Parent Company”); each of the owners of Target Parent Company and beneficial owners of the Target Company, Real Estate Target Company and Target Parent Company (collectively along with Target Parent Company, the “Sellers”); and Phillip Davis, as Seller Representative. On the Closing Date, the Target Company merged into Alliance Machines, which survived as an indirect wholly owned subsidiary of the Company. The Target Company operates a machine shop in Vernal, Utah, providing specialized welding, repair, rebuilding, and machining services for drilling and other equipment, primarily in Utah and the surrounding states. In connection with the closing of the transaction, excluding the separate real-estate transaction described below, the Company paid the Sellers aggregate consideration of (i) $350,000 (the “Cash Consideration”) and (ii) issued 75,000 shares (the “Stock Consideration”) of the Company’s 10% Series A Cumulative Perpetual Preferred Stock, par value $0.001 per share (the “Series A Preferred Stock”), subject to customary adjustments for debt, cash on hand, transaction expenses and net working capital. At the closing, $50,000 of the Cash Consideration and 5,000 shares of the Stock Consideration were held in escrow to satisfy the Sellers’ indemnification and purchase-price adjustment obligations under the Purchase Agreement. The Purchase Agreement also provides for the acquisition of the Owned Real Property (as defined in the Purchase Agreement) by a merger of Real Estate Target Company into New Real Estate Sub at a separate closing (the “Real Estate Closing”), subject to satisfaction or waiver of the applicable closing conditions, for $150,000 in cash and 35,000 shares of Series A Preferred Stock. If certain conditions of the Purchase Agreement have not been satisfied or waived by February 28, 2027, the Company has the option to forego the purchase of the Owned Real Property. Alliance Machines also entered into a lease with the Real Estate Target Company for the continued use of the Owned Real Property. The foregoing description of the Purchase Agreement does not purport to be complete and is subject to and qualified in its entirety by the full text of the Purchase Agreement, a copy of which is filed as Exhibit 10.1 to this Current Report on Form 8-K and incorporated into this Item 1.01 by reference.

Item 3.02. Unregistered Sales of Equity Securities. The Company issued the 75,000 shares of Stock Consideration to certain of the Sellers on October 23, 2026, as partial consideration pursuant to the Purchase Agreement. The shares were issued without an underwriter or placement agent in a transaction exempt from registration pursuant to Section 4(a)(2) of the Securities Act of 1933, as amended, and Rule 506 of Regulation D promulgated thereunder.

Item 7.01. Regulation FD Disclosure. On October 26, 2026, the Company issued a press release announcing the transaction. A copy of the press release is furnished herewith as Exhibit 99.1.