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

Rhea-AI Filing Summary

Richard B. Rowley, a director of Orange County Bancorp, Inc. (OBT), reported changes in his beneficial ownership. The filing shows a disposition of 537,263 common shares. The report also records an acquisition of 56 phantom stock units that are economically equivalent to one share each and become payable upon the reporting person’s separation from service. After the reported transactions, the filing shows 21,582 shares of common stock beneficially owned directly by the reporting person. The filing discloses restricted stock units that vest either immediately upon grant or on February 20, 2026, and that those RSUs are settled in shares of the issuer’s common stock upon separation from service.

Positive

• Retention of equity‑linked compensation via 56 phantom stock units and restricted stock units aligns the director’s economic interests with shareholders over time
• RSUs include a defined vesting date (February 20, 2026), providing clarity on timing for at least some awards

Negative

• Large disposal of 537,263 common shares materially reduced the director’s direct holdings as reported
• No rationale provided in the filing for the sale, leaving investors without context about whether the sale was routine, personal liquidity, or other

Insights

Financial Analyst

TL;DR: Director sold a large block of common stock while receiving long‑term‑style compensation in phantom shares and RSUs.

The disposition of 537,263 common shares is the most material line item and could reflect personal liquidity or rebalancing; the filing does not state the reason for the sale. The grant of 56 phantom stock units and the presence of RSUs that vest on separation (including those vesting on February 20, 2026) indicate continued compensation tied to equity value. Net direct beneficial ownership after these transactions is shown as 21,582 shares. No information on the issuer’s total shares outstanding or percentage ownership is included, so the filing alone cannot quantify the disposal’s ownership impact on a percentage basis.

Corporate Governance Expert

TL;DR: A director reduced direct holdings substantially while retaining deferred/equity‑linked awards.

The combination of a large sale and retention of phantom units and RSUs suggests the reporting person maintains some ongoing economic exposure to the company through deferred awards while materially lowering direct share holdings. The RSU settlement terms tie payout to separation from service rather than time‑based vesting alone, which affects when those shares convert to actual ownership. The filing does not disclose any 10b5‑1 plan or the rationale for the transactions, so governance context is limited.

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^*

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)
09/02/2025

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)	09/02/2025		A		$56		(3)	(3)	Common Stock	56	$26.52	21,582	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	09/04/2025
	** 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 did Orange County Bancorp (OBT) director Richard B. Rowley report on the Form 4?

The filing reports a disposition of 537,263 common shares, an acquisition of 56 phantom stock units, and resulting direct beneficial ownership of 21,582 shares.

Do the reported phantom stock units convert to actual shares for OBT?

Yes; the filing states each phantom stock unit is the economic equivalent of one common share and becomes payable upon the reporting person’s separation from service.

Are there restricted stock units (RSUs) in the report and when do they vest?

Yes; the filing includes RSUs that vest 100% as of the grant date and additional RSUs that vest 100% on February 20, 2026, settled in common stock upon separation from service.

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

The filing shows 21,582 shares of common stock beneficially owned directly following the reported transactions.

Does the Form 4 explain why the 537,263 shares were sold?

No; the filing discloses the transaction but does not state a reason for the disposition.