[Form 4] Star Equity Holdings, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Jeffrey E. Eberwein, who serves as Chief Executive Officer, a director and a 10% owner, reported multiple transactions in Star Equity Holdings, Inc. The Form 4 shows restricted stock and open-market purchases of common stock on September 15-17, 2025: 8,918 restricted shares granted (valued at $0 in the filing), then purchases of 10,402 shares at $9.62, 11,395 shares at $9.96 and 12,000 shares at $10.94, bringing his common stock holdings to 651,595 shares after the last trade. The filing also reports dispositions of Series A Preferred Stock in amounts of 9,076, 11,948 and 10,081 shares on the same dates at prices around $9.20–$9.24, reflecting reductions in the preferred holdings reported to 1,151,072 shares. The restricted shares vest after one year and represent a portion of his elected compensation.

Positive

• CEO and director increased common stock ownership via purchases and restricted stock grants, aligning management and shareholder interests
• Restricted stock election (50% of base salary) creates longer-term alignment subject to one-year vesting
• Multiple open-market purchases provide recent market-price reference points ($9.62, $9.96, $10.94)

Negative

• Dispositions of Series A Preferred Stock on the same dates reduced preferred holdings (9,076; 11,948; 10,081 shares), indicating a shift in the insider’s capital structure exposure
• Form does not disclose rationale for reallocating from preferred to common stock, leaving purpose unclear

Insights

Financial Analyst

TL;DR: CEO increased common stock holdings through purchases and restricted stock, aligning interests with shareholders.

The pattern of purchases over three days and the grant of restricted stock indicates an increase in the reporting person’s economic stake in the company’s common equity. The prices paid ($9.62, $9.96, $10.94) provide recent transaction-level valuation points for the market’s view of equity value. The restricted stock election (50% of base salary paid in restricted shares) creates ongoing alignment subject to vesting. Concurrent dispositions of Series A Preferred Stock are documented; since those preferred shares are non-convertible, the transactions appear to shift the reporting person’s holding mix toward common equity rather than change total economic exposure materially.

Corporate Governance Expert

TL;DR: Insider activity is notable for alignment but mixed due to simultaneous preferred share dispositions.

As CEO and a director, reported purchases are governance-positive because they increase insider ownership of common stock, enhancing alignment with public shareholders. The restricted stock compensation election is a formalized alignment mechanism that vests after one year. The reported sales of Series A Preferred Stock on the same dates reduce preferred holdings; because those preferred shares are not convertible, the filings do not indicate dilution risk but do show a rebalancing of the insider’s portfolio. Overall, this is a material insider reallocation but not clearly adverse to minority shareholders.

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

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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)
09/15/2025

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	09/15/2025		A		8,918(1)	A	$0	617,798	D
Common Stock	09/15/2025		P		10,402	A	$9.62	628,200	D
Common Stock	09/16/2025		P		11,395	A	$9.96	639,595	D
Common Stock	09/17/2025		P		12,000	A	$10.94	651,595	D
Series A Preferred Stock(2)	09/15/2025		S		9,076	D	$9.24	1,173,101	D
Series A Preferred Stock(2)	09/16/2025		S		11,948	D	$9.24	1,161,153	D
Series A Preferred Stock(2)	09/17/2025		S		10,081	D	$9.2	1,151,072	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. Includes 8,918 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.

2. Star Equity Holdings, Inc. 10% Series A Cumulative Perpetual Preferred Stock, which is not convertible or exchangeable into Star Equity Holdings, Inc. Common Stock.

Remarks:

	/s/ Jeffrey E. Eberwein	09/17/2025
	** 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).
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FAQ

What insider transactions did Jeffrey E. Eberwein report for STRRP on the Form 4?

The filing reports a grant of 8,918 restricted common shares and open-market purchases of common stock (10,402 at $9.62; 11,395 at $9.96; 12,000 at $10.94) on September 15–17, 2025, plus dispositions of Series A Preferred Stock (9,076; 11,948; 10,081) at about $9.20–$9.24.

How many common shares does the reporting person own after the transactions?

The Form 4 reports the reporting person beneficially owning 651,595 shares of common stock after the September 17, 2025 transaction.

Are the restricted shares immediately transferable?

No. The 8,918 restricted shares vest on the first anniversary of the grant date according to the issuer's 2009 Incentive Stock and Awards Plan as amended and restated.

Did the reporting person sell any securities?

Yes. The filing shows dispositions of Series A Preferred Stock on September 15, 16 and 17, 2025, reducing preferred holdings to 1,151,072 shares.

Does the Form 4 indicate whether the Series A Preferred Stock converts to common stock?

The filing states the Series A Preferred Stock is not convertible or exchangeable into common stock.