[Form 4] Orange County Bancorp, Inc. /DE/ Insider Trading Activity

Rhea-AI Filing Summary

Sousa Gregory reported acquisition or exercise transactions in this Form 4 filing.

Orange County Bancorp EVP and Deputy CLO Gregory Sousa reported updated equity holdings and a new compensation grant. He now holds 13,619 shares of common stock directly and 7,065 shares indirectly through a 401(k) plan. The direct holdings include restricted stock units that vest in equal annual installments starting on March 21, 2025, March 20, 2026, and March 19, 2027. Sousa also received a grant of phantom stock interests under a Performance-Based SERP representing 25 underlying shares of common stock at a deemed price of $35.35 per share, bringing his phantom stock balance to 4,969 units. The filing notes some underlying transactions were not required to be reported under Section 16 rules, indicating these updates are largely administrative and compensation-related rather than open-market trading.

Insights

Equity compensation analyst

Routine equity and phantom stock awards update Sousa’s long-term incentives.

The filing shows Gregory Sousa, EVP and Deputy CLO of Orange County Bancorp, receiving a compensation-related award of phantom stock under a Performance-Based SERP, linked to 25 shares of common stock at $35.35. This is not an open-market purchase or sale.

The phantom stock interests, now totaling 4,969 units, are designed to track the value of common stock and may be settled in shares upon distribution, according to the plan’s terms and Sousa’s prior elections. Direct holdings of 13,619 shares and 7,065 shares via a 401(k) provide additional equity exposure.

The filing characterizes some activity as not required to be reported under Section 16, supporting the view that this is largely administrative and compensation-focused. Future company filings may provide more detail on performance conditions tied to the Performance-Based SERP.

Insider Trade Summary

3 transactions reported

Mixed 3 txns

Insider Sousa Gregory

Role EVP and Deputy CLO

Type	Security	Shares	Price	Value
Grant/Award	Phantom Stock	0	$35.35	--
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Phantom Stock — 4,969 shares (Direct, null); Common Stock — 13,619 shares (Direct, null); Common Stock — 7,065 shares (Indirect, By 401(k))

Footnotes (1)

1. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 20, 2026. Restricted stock units which vest at a rate of 1/3 per year commencing on March 19, 2027. Reflects transactions not required to be reported pursuant to Section 16 of the Securities Exchange Act of 1934, as amended. Represents deemed investments in connection with the Performance-Based SERP. Phantom stock interests under the Performance-Based SERP may be settled in shares of Company stock upon distribution to the reporting person, based on their prior election.

Key Figures

Direct common stock holdings: 13,619 shares 401(k) common stock holdings: 7,065 shares Phantom stock balance: 4,969 units +2 more

5 metrics

Direct common stock holdings 13,619 shares Total direct holdings following transaction

401(k) common stock holdings 7,065 shares Indirect holdings via 401(k) following transaction

Phantom stock balance 4,969 units Phantom stock interests under Performance-Based SERP after grant

Underlying shares for new phantom award 25 shares Common stock equivalent for latest phantom stock grant

Deemed price for phantom stock $35.35 per share Transaction price per share for phantom stock award

Key Terms

Phantom stock, Performance-Based SERP, restricted stock units, Section 16 of the Securities Exchange Act of 1934

4 terms

Phantom stock financial

"Represents deemed investments in connection with the Performance-Based SERP. Phantom stock interests under the Performance-Based SERP may be settled in shares of Company stock"

A phantom stock is a form of compensation that gives employees or executives the benefits of stock ownership, such as the increase in stock value, without actually giving them real shares. It acts like a promise to pay the employee the equivalent value of company stock later, often as a bonus or incentive. This allows companies to motivate and reward staff without diluting ownership or transferring actual shares.

Performance-Based SERP financial

"Represents deemed investments in connection with the Performance-Based SERP. Phantom stock interests under the Performance-Based SERP may be settled in shares"

restricted stock units financial

"Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025."

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

Section 16 of the Securities Exchange Act of 1934 regulatory

"Reflects transactions not required to be reported pursuant to Section 16 of the Securities Exchange Act of 1934, as amended."

A provision of federal securities law that requires company insiders—directors, officers and large shareholders—to publicly report their stock holdings and trades and to surrender any “short-swing” profits from purchases and sales within a six-month window. It acts like a rule that forces leaders to announce their trades and prevents quick buy-sell windfalls, giving investors transparency into insider activity and reducing opportunities for unfair gain.

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Form 4 Insider Transactions: What Each Field Means →

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^*

Sousa Gregory

(Last) (First) (Middle)

212 DOLSON AVENUE

(Street)

MIDDLETOWN NEW YORK 10940

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Orange County Bancorp, Inc. /DE/ [ OBT ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	EVP and Deputy CLO

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/15/2026

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)
			Code	V	Amount	(A) or (D)	Price
Common Stock								13,619(1)(2)(3)	D
Common Stock								7,065(4)	I	By 401(k)

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
Phantom Stock	(5)	06/15/2026		A		$25		(5)	(5)	Common Stock	25	$35.35	4,969	D

Explanation of Responses:

1. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

2. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 20, 2026.

3. Restricted stock units which vest at a rate of 1/3 per year commencing on March 19, 2027.

4. Reflects transactions not required to be reported pursuant to Section 16 of the Securities Exchange Act of 1934, as amended.

5. Represents deemed investments in connection with the Performance-Based SERP. Phantom stock interests under the Performance-Based SERP may be settled in shares of Company stock upon distribution to the reporting person, based on their prior election.

	/s/ Jennifer Staub, pursuant to power of attorney	06/16/2026
	** 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)