Orange County Bancorp insider purchase at $24.02; updated holdings

Rhea-AI Filing Summary

Orange County Bancorp, Inc. (OBT) reported insider open‑market purchases by its President and CEO, who is also a director. On 10/31/2025, the insider bought 1,300 shares of common stock at $24.02 per share in a direct account and 350 shares at $24.02 per share through an IRA.

Following these transactions, the insider beneficially owned 106,788 common shares directly and 16,200 common shares indirectly via an IRA. The filing also lists 21,919 phantom stock units, each economically equivalent to one common share and payable upon separation of service as a director. Direct holdings include restricted stock units that vest over time, as described in the notes.

Insider Trade Summary

Net Buyer: 1,650 shares ($39,633)

Net Buy 3 txns

Insider Gilfeather Michael J

Role President and CEO

Bought 1,650 shs ($40K)

Type	Security	Shares	Price	Value
Purchase	Common Stock	1,300	$24.02	$31K
Purchase	Common Stock	350	$24.02	$8K
holding	Phantom Stock	--	--	--

Holdings After Transaction: Common Stock — 106,788 shares (Direct); Common Stock — 16,200 shares (Indirect, By IRA); Phantom Stock — 21,919 shares (Direct)

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)
10/31/2025

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	10/31/2025		P		1,300	A	$24.02	106,788(1)(2)(3)(4)	D
Common Stock	10/31/2025		P		350	A	$24.02	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)							(5)	(5)	Common Stock	21,919		21,919	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	11/03/2025
	** 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 insider transactions did OBT report?

On 10/31/2025, the insider purchased 1,300 shares at $24.02 directly and 350 shares at $24.02 through an IRA.

How many OBT shares does the insider own after the trades?

The insider beneficially owns 106,788 common shares directly and 16,200 common shares indirectly via an IRA.

What is the role of the reporting person at OBT?

The reporting person is a Director and serves as President and CEO.

What are the phantom stock units disclosed for OBT?

The filing lists 21,919 phantom stock units, each equal in value to one common share, payable upon separation of service as a director.

Do the insider’s direct holdings include restricted stock units?

Yes. Direct holdings include restricted stock units that vest on schedules noted in the filing.

What is the OBT ticker symbol?

The ticker symbol is OBT.