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

Rhea-AI Filing Summary

Orange County Bancorp, Inc. reported an insider equity transaction by its President and CEO, who also serves as a director. On 12/16/2025, the insider acquired 136 shares of phantom stock, each economically equivalent to one share of common stock, at $28.95 per unit. These phantom stock units become payable when the insider separates from service as a director.

Following the reported transactions, the insider beneficially owns 106,788 shares of common stock directly and 16,200 shares indirectly through an IRA, along with 22,055 phantom stock units. The common stock totals include several blocks of restricted stock units that vest in stages between March 2024 and December 2026.

Insider Trade Summary

3 transactions reported

Mixed 3 txns

Insider Gilfeather Michael J

Role President and CEO

Type	Security	Shares	Price	Value
Grant/Award	Phantom Stock	136	$28.95	$4K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Phantom Stock — 22,055 shares (Direct); Common Stock — 106,788 shares (Direct); Common Stock — 16,200 shares (Indirect, By IRA)

Footnotes (1)

1. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024. Includes restricted stock units which vest on December 31, 2026. 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. 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.

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^*

Gilfeather Michael J

(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
X	Officer (give title below)		Other (specify below)
	President and CEO

3. Date of Earliest Transaction (Month/Day/Year)
12/16/2025

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								106,788(1)(2)(3)(4)	D
Common Stock								16,200	I	By IRA

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)	12/16/2025		A		136		(5)	(5)	Common Stock	136	$28.95	22,055	D

Explanation of Responses:

1. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

2. Includes restricted stock units which vest on December 31, 2026.

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

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

5. 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	12/17/2025
	** 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).
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