Star Equity CEO increases common stake and gifts preferred shares to charity

Rhea-AI Filing Summary

Jeffrey E. Eberwein, who serves as Chief Executive Officer, a director and a reported >10% owner of Star Equity Holdings, Inc. (STRR), reported small open-market purchases of the company’s common stock and a charitable donation of preferred shares. On 09/29/2025 he purchased 5,000 shares of common stock at $11.31 each, bringing his beneficial common holdings to 679,147 shares. On 09/30/2025 he purchased an additional 2,600 common shares at $11.20, increasing his holdings to 681,747 shares.

Also on 09/30/2025 the filing reports a disposition of 20,000 shares of Series A preferred stock, explained as a charitable gift to a donor-advised fund. The Form 4 discloses that after the reported preferred transaction the reported beneficial preferred position is shown as 1,131,072 shares (reported as indirect ownership). The filing notifies investors of these insider transactions and the reporting person’s roles with the issuer.

Positive

• Insider increased direct common-stock holdings with purchases of 5,000 shares at $11.31 and 2,600 shares at $11.20
• Clear disclosure of charitable gift—the 20,000 Series A preferred shares disposition is identified as a donation to a donor-advised fund
• Reporting person holds multiple roles (CEO, director, >10% owner), so disclosures provide meaningful transparency for investors

Negative

• None.

Insights

Financial Analyst

TL;DR: Insider made modest purchases of common stock and a charitable gift of preferred shares; overall insider stake remains substantial.

The purchases on 09/29 and 09/30/2025 (5,000 shares at $11.31 and 2,600 shares at $11.20) are small relative to the reported common shareholding of ~681,747, indicating incremental insider accumulation rather than a material change in control. The 20,000-share disposition of Series A preferred is identified as a charitable gift to a donor-advised fund, which is a non-economic transfer for the reporting person. For investors, these transactions are routine insider activity that increases transparency about the CEO/director’s current positions but do not, by themselves, indicate a material shift in governance or capital structure.

Corporate Governance Expert

TL;DR: Disclosure is complete and consistent with Section 16 reporting; transactions appear routine and the gift is properly explained.

The Form 4 identifies the reporting person as CEO, director and a >10% owner, which makes these disclosures particularly relevant to governance watchers. The charitable disposition is explicitly explained as a gift to a donor-advised fund, satisfying common disclosure expectations about the nature of non-market dispositions. The combined purchases slightly increase the insider’s direct common share stake, while the gift reduces his preferred holdings; neither action alters board composition or control based on the information provided.

SEC Form 4

FORM 4

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
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

1. Name and Address of Reporting Person^*

Eberwein Jeffrey E.

(Last) (First) (Middle)

53 FOREST AVENUE, SUITE 102

(Street)

OLD GREENWICH CT 06870

(City) (State) (Zip)

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

3. Date of Earliest Transaction (Month/Day/Year)
09/29/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	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	09/29/2025		P		5,000	A	$11.31	679,147	D
Common Stock	09/30/2025		P		2,600	A	$11.2	681,747	D
Series A Preferred Stock	09/30/2025		S		20,000	D	(1)	1,131,072	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 (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	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 (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (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: 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

Explanation of Responses:

1. The reported transaction represents the Reporting Person's charitable gift to a donor advised fund.

Remarks:

	/s/ Jeffrey E. Eberwein	10/01/2025
	** Signature of Reporting Person	Date
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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What insider transactions did STRR CEO Jeffrey E. Eberwein report?

He reported purchases of 5,000 common shares at $11.31 on 09/29/2025 and 2,600 common shares at $11.20 on 09/30/2025, plus a disposition of 20,000 Series A preferred shares.

Why was 20,000 Series A preferred stock disposed of according to the Form 4?

The filing explains the 20,000-share disposition as a charitable gift to a donor-advised fund.

How many common shares does Jeffrey E. Eberwein beneficially own after the reported purchases?

The Form 4 shows beneficial common ownership increasing to 681,747 shares after the reported transactions.

Does the Form 4 indicate Jeffrey E. Eberwein’s relationship to STRR?

Yes. The form lists him as Chief Executive Officer, a director, and a >10% owner of Star Equity Holdings, Inc. (STRR).

Were the common stock purchases open-market transactions?

The transaction codes reported are "P" for the common stock purchases, which indicates acquisitions pursuant to a Rule 10b5-1 trading plan or similar pre-arranged purchase method as defined in Form 4 instructions.