How were the Star Equity share purchase prices disclosed in the Form 4 footnotes?

The filing states that reported prices are weighted averages, rounded to the nearest cent. It notes purchases occurred in multiple trades between $10.09–$10.11 on May 19, $9.78–$10.33 on May 20, and $10.82–$10.96 on May 21, 2026, inclusive.

CEO Jeffrey Eberwein adds Star Equity (NASDAQ: STRR) shares in May 2026 buys

Filing Impact

(High)

Filing Sentiment

(Positive)

Form Type

Rhea-AI Filing Summary

Star Equity Holdings, Inc. Chief Executive Officer Jeffrey E. Eberwein reported open-market purchases of a total of 18,403 shares of common stock at weighted average prices around $10 per share over three days in May 2026. Following these transactions, he directly holds 1,059,384 common shares.

He also settled 860 Restricted Stock Units that had been granted in 2025, receiving 860 shares of 10.0% Series A Cumulative Perpetual Preferred Stock upon their scheduled vesting on May 19, 2026. This RSU settlement is a non-cash, compensation-related conversion rather than a market trade.

Insider Trade Summary

Net Buyer: 18,403 shares ($189,123)

Net Buy 5 txns

Insider Eberwein Jeffrey E.

Role Chief Executive Officer

Bought 18,403 shs ($189K)

Type	Security	Shares	Price	Value
Purchase	Common Stock.	4,198	$10.90	$46K
Purchase	Common Stock.	406	$10.18	$4K
Exercise	Restricted Stock Unit	860	$0.00	--
Exercise	Series A Preferred Stock	860	$0.00	--
Purchase	Common Stock.	13,799	$10.09	$139K

Holdings After Transaction: Common Stock. — 1,059,384 shares (Direct, null); Restricted Stock Unit — 0 shares (Direct, null); Series A Preferred Stock — 765,077 shares (Direct, null)

Footnotes (1)

Each Restricted Stock Unit represents the right to receive, at settlement, one share of the Issuer's 10.0% Series A Cumulative Perpetual Preferred Stock, par value $0.001 per share (the "Series A Preferred Stock"). This transaction represents the settlement of Restricted Stock Units in shares of Series A Preferred Stock on their scheduled vesting date. 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 $10.09 to $10.11 on May 19, 2026, $9.78 to $10.33 on May 20, 2026, and $10.82 to $10.96 on May 21, 2026, rounded to the nearest cent, 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. On May 19, 2025, the Reporting Person was granted Restricted Stock Units by Star Operating Companies, Inc. ("SOC"), each of which represented the right to receive, at settlement, one share of SOC Series A Preferred Stock ("SOC RSUs"). Pursuant to the Agreement and Plan of Merger, dated as of May 21, 2025, by and among SOC, the Issuer and HSON Merger Sub, Inc., a wholly owned subsidiary of the Issuer, the Reporting Person's SOC RSUs were exchanged for 860 Restricted Stock Units. As to this grant, one hundred percent (100%) of the Restricted Stock Units vested on May 19, 2026.

Key Figures

Common shares bought: 18,403 shares Purchase prices: $9.78–$10.96 per share Common shares after transactions: 1,059,384 shares +2 more

5 metrics

Common shares bought 18,403 shares Open-market purchases in May 2026

Purchase prices $9.78–$10.96 per share Weighted average ranges over May 19–21, 2026

Common shares after transactions 1,059,384 shares Direct holdings following May 21, 2026 purchase

RSUs settled 860 units Restricted Stock Units vesting into preferred shares on May 19, 2026

Preferred shares received 860 shares 10.0% Series A Cumulative Perpetual Preferred Stock from RSU settlement

Key Terms

Restricted Stock Unit, 10.0% Series A Cumulative Perpetual Preferred Stock, weighted average price, Agreement and Plan of Merger

4 terms

Restricted Stock Unit financial

"The Reporting Person was granted Restricted Stock Units by Star Operating Companies, Inc."

A restricted stock unit is a promise from a company to give an employee shares of stock after certain conditions are met, like staying with the company for a set amount of time. It’s like earning a bonus that turns into company stock once you’ve proven your commitment, making it a way to motivate and reward employees.

10.0% Series A Cumulative Perpetual Preferred Stock financial

"one share of the Issuer's 10.0% Series A Cumulative Perpetual Preferred Stock"

weighted average price financial

"The price reported in Column 4 is a weighted average price, rounded to the nearest cent."

Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.

Agreement and Plan of Merger financial

"Pursuant to the Agreement and Plan of Merger, dated as of May 21, 2025"

An Agreement and Plan of Merger is a formal document where two companies agree to combine into one, outlining how the process will happen. It’s like a step-by-step plan for merging, and it matters because it shows both sides have agreed on the details before the official transition takes place.

Form 4 Insider Transactions: What Each Field Means →

05/21/2026 - 05:55 PM

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
Estimated average burden
hours per response:			0.5

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

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Eberwein Jeffrey E.

(Last)

(First)

(Middle)

53 FOREST AVENUE, SUITE 101

(Street)

OLD GREENWICH

CONNECTICUT

06870

(City)

(State)

(Zip)

UNITED STATES

(Country)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/19/2026

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

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

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

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Series A Preferred Stock	05/19/2026		M		860	A	⁽¹⁾⁽²⁾	765,077	D
Common Stock.	05/19/2026		P		13,799	A	$10.09⁽³⁾	1,054,780	D
Common Stock.	05/20/2026		P		406	A	$10.18⁽³⁾	1,055,186	D
Common Stock.	05/21/2026		P		4,198	A	$10.9⁽³⁾	1,059,384	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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Restricted Stock Unit	⁽¹⁾⁽²⁾	05/19/2026		M			860	⁽⁴⁾	⁽⁴⁾	Series A Preferred Stock	860	⁽¹⁾	0	D

Explanation of Responses:

1. Each Restricted Stock Unit represents the right to receive, at settlement, one share of the Issuer's 10.0% Series A Cumulative Perpetual Preferred Stock, par value $0.001 per share (the "Series A Preferred Stock").

2. This transaction represents the settlement of Restricted Stock Units in shares of Series A Preferred Stock on their scheduled vesting date.

3. 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 $10.09 to $10.11 on May 19, 2026, $9.78 to $10.33 on May 20, 2026, and $10.82 to $10.96 on May 21, 2026, rounded to the nearest cent, 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.

4. On May 19, 2025, the Reporting Person was granted Restricted Stock Units by Star Operating Companies, Inc. ("SOC"), each of which represented the right to receive, at settlement, one share of SOC Series A Preferred Stock ("SOC RSUs"). Pursuant to the Agreement and Plan of Merger, dated as of May 21, 2025, by and among SOC, the Issuer and HSON Merger Sub, Inc., a wholly owned subsidiary of the Issuer, the Reporting Person's SOC RSUs were exchanged for 860 Restricted Stock Units. As to this grant, one hundred percent (100%) of the Restricted Stock Units vested on May 19, 2026.

Remarks:

	/s/ Jeffrey E. Eberwein	05/21/2026
	** 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.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transactions did Star Equity (STRR) report for Jeffrey E. Eberwein?

Jeffrey E. Eberwein reported buying 18,403 Star Equity common shares in open-market transactions and settling 860 Restricted Stock Units into 10.0% Series A Preferred Stock. These moves increased his direct equity exposure through both common and preferred shares.

How many Star Equity common shares did the CEO buy and at what prices?

He bought 18,403 common shares in three trades: 13,799 shares on May 19, 406 shares on May 20, and 4,198 shares on May 21, 2026. Weighted average prices ranged from about $9.78 to $10.96 per share, based on detailed footnote disclosure.

What are Jeffrey E. Eberwein’s Star Equity holdings after these transactions?

After the reported purchases, Jeffrey E. Eberwein directly owns 1,059,384 Star Equity common shares. This total reflects his position following the May 21, 2026 transaction and shows that the new buys added to an already substantial existing stake in the company.

What happened with the 860 Restricted Stock Units reported in the filing?

The 860 Restricted Stock Units vested and were settled into 860 shares of 10.0% Series A Cumulative Perpetual Preferred Stock on May 19, 2026. This was a scheduled equity compensation event, converting RSUs into preferred shares without an open-market purchase or sale.

What was the origin of the 860 Restricted Stock Units that vested in 2026?

The footnotes explain that these RSUs were originally granted on May 19, 2025 by Star Operating Companies, Inc. and later exchanged into 860 Star Equity RSUs under a merger agreement. One hundred percent of the exchanged RSUs vested on May 19, 2026.