Sec Form 4 Filing - Eberwein Jeffrey E. @ Star Equity Holdings, Inc. - 2026-05-22

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Eberwein Jeffrey E. 2. Issuer Name and Ticker or Trading Symbol Star Equity Holdings, Inc. [ STRR] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director X __ 10% Owner X __ Officer (give title below) _____ Other (specify below) Chief Executive Officer (Last) (First) (Middle) 53 FOREST AVENUE, SUITE 101 3. Date of Earliest Transaction (MM/DD/YY) 05/22/2026 (Street) OLD GREENWICH, CT06870 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock. 05/22/2026 P 694 A $ 11.06 ( 1 ) 1,060,078 ( 2 ) D Common Stock. 05/26/2026 P 2,414 A $ 11.51 ( 1 ) 1,062,492 ( 2 ) D Common Stock. 05/27/2026 P 2,288 A $ 11.76 ( 1 ) 1,064,780 ( 2 ) D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Eberwein Jeffrey E. 53 FOREST AVENUE, SUITE 101 OLD GREENWICH, CT06870 X X Chief Executive Officer Signatures /s/ Jeffrey E. Eberwein 05/27/2026 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The price reported in Column 4 is a weighted average price, rounded to the nearest cent. These shares were purchased in multiple transactions at prices ranging from $10.90 to $11.26 on May 22, 2026, $11.40 to $11.51 on May 26, 2026, and $11.51 to $11.76 on May 27, 2026, inclusive. 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 purchased at each separate price such shares were purchased. ( 2 )Includes (i) 21,125 shares of restricted stock credited to the Reporting Person's account under the Issuer's 2009 Incentive Plan; (ii) 6,750 RSUs; and (iii) 1,036,905 shares of common stock. Excludes 1,690 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.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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