X0609 4 2026-10-14 0 0001210708 Star Equity Holdings, Inc. STRR 0001548312 Eberwein Jeffrey E. false C/O STAR EQUITY HOLDINGS, INC. 53 FOREST AVENUE, SUITE 101 OLD GREENWICH CT 06870 1 1 1 0 Chief Executive Officer 1 Series A Preferred Stock 2026-10-14 4 S 0 1000 9.10 D 755937 D Series A Preferred Stock 2026-10-15 4 S 0 1001 9.14 D 754936 D Series A Preferred Stock 2026-10-16 4 S 0 1000 9.16 D 753936 D Common Stock. 2026-10-15 4 A 0 6257 0 A 1137359 D The sale reported on this Form 4 was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person and assumed by Clear Street LLC, providing for the sale of shares of the Issuer's Series A Cumulative Perpetual Preferred Stock, par value $0.001 per share. Sales under the plan were permitted to begin on October 1, 2026, and the plan expires on October 1, 2028, unless terminated earlier. The price reported in Column 4 is a weighted average price, rounded to the nearest cent. These shares were sold in multiple transactions at prices ranging from $9.06 to $9.11 on October 14, 2026, $9.06 to $9.60 on October 15, 2026, and $9.16 to $9.24 on October 16, 2026. The Reporting Person undertakes to provide the Issuer and any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price such shares were sold. Includes 6,257 shares of restricted stock credited to the Reporting Person's account under the Issuer's 2009 Incentive Stock and Awards Plan, as amended and restated. Mr. Eberwein has elected to receive fifty percent of his base salary in the form of such restricted stock. Each share of restricted stock shall vest upon the first anniversary of the grant date and represents the right to receive, at settlement, one share of common stock. Includes (i) 23,852 shares of restricted stock and (ii) 6,750 RSUs credited to the Reporting Person's account under the Issuer's 2009 Incentive Stock and Awards Plan, as amended and restated; and (iii) 1,106,757 shares of common stock. Excludes 2,000 shares indirectly owned in contributory 401(k) and IRA accounts. Each share of restricted stock and each RSU represents the right to receive, at settlement, one share of common stock. /s/ Jeffrey E. Eberwein 2026-10-16