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

Rhea-AI Filing Summary

Richard B. Rowley, a director of Orange County Bancorp, Inc. (OBT), reported changes in his beneficial ownership on 09/16/2025. The filing shows a disposition of 537,263 shares of common stock and a reported ownership balance of 21,691 shares following the transactions. On 09/16/2025 he also acquired 108 units of phantom stock that are economically equivalent to 108 shares and become payable upon his separation as a director. The filing discloses restricted stock units: some vest 100% as of grant and others vest 100% on February 20, 2026, and are settled in common stock upon separation. The form was signed under power of attorney on 09/17/2025.

Positive

• Retained direct ownership: the reporting person continues to hold 21,691 shares after the reported transactions.
• Deferred alignment: presence of RSUs and phantom stock ties future director compensation to the company's share performance or separation events.

Negative

• Large disposition: a reported disposal of 537,263 common shares on 09/16/2025 represents a substantial reduction in reported holdings.
• Concentration of deferred payouts: certain awards vest or pay out only upon separation, which may delay economic alignment with current shareholders.

Insights

Securities Analyst

TL;DR: Large disposal recorded with remaining direct ownership and director phantom/RSU holdings creating deferred economic exposure.

The Form 4 documents a material reduction in reported common stock holdings by the director through a 537,263-share disposition on 09/16/2025 while leaving 21,691 shares held directly post-transaction. The filing also recognizes 108 phantom stock units and RSUs with differing vesting terms, which provide deferred value payable in shares upon separation. These instruments preserve some alignment with shareholder outcomes despite the reported disposal. All items are presented as direct holdings and the filing is executed under power of attorney.

Corporate Governance Expert

TL;DR: Director disposition is notable; retained equity and deferred awards maintain partial alignment with shareholders.

The report highlights a significant disposal by a director, coupled with retained direct ownership and deferred compensation in the form of RSUs and phantom stock. The RSUs include one tranche vesting on February 20, 2026 and another that vests 100% as of grant but settles upon separation, while phantom units convert to a cash/share equivalent at separation. Documentation appears complete and signed by an authorized agent on 09/17/2025.

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).

1. Name and Address of Reporting Person^*

Rowley Richard B

(Last) (First) (Middle)

212 DOLSON AVENUE

(Street)

MIDDLETOWN NY 10940

(City) (State) (Zip)

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)

X	Director		10% Owner
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
09/16/2025

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								537,263(1)(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 (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	(3)	09/16/2025		A		$108		(3)	(3)	Common Stock	108	$25.95	21,691	D

Explanation of Responses:

1. Includes restricted stock units which vest 100% as of the date of grant and are settled in shares of Issuer common stock upon separation from service of the reporting person.

2. Includes restricted stock units which vest 100% on February 20, 2026 and are settled in shares of Issuer common stock upon separation from service of the reporting person.

3. Each share of phantom stock is the economic equivalent of one share of common stock and becomes payable upon the reporting person's separation of service as a director.

	/s/ Jennifer Staub, pursuant to power of attorney	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).
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 transactions did Richard B. Rowley report on Form 4 for OBT?

The filing reports a disposition of 537,263 shares of common stock on 09/16/2025 and the acquisition of 108 phantom stock units on the same date.

How many OBT shares does the reporting person own after the reported transactions?

The reporting person beneficially owns 21,691 shares following the reported transactions.

What are the vesting terms disclosed in the Form 4 for RSUs?

The filing states some RSUs vest 100% as of the date of grant and others vest 100% on February 20, 2026; all are settled in common stock upon separation.

What is the nature of the phantom stock reported?

Each phantom stock unit is the economic equivalent of one share of common stock and becomes payable upon the reporting person's separation of service as a director.

Who signed the Form 4 and when was it filed?

The form was signed under power of attorney by Jennifer Staub and dated 09/17/2025.