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

Rhea-AI Filing Summary

Orange County Bancorp, Inc. (OBT) director Gregory F. Holcombe reported a set of equity transactions dated 10/01/2025. The filing shows a disposition of 68,953 shares of common stock. It also reports indirect holdings through entities: 14,920 shares held by a foundation, 69,440 shares held by an LLC, and 12,054 shares held in trust. The report lists phantom stock totaling 872 units (each unit economically equivalent to one common share) and restricted stock units (RSUs) that include one grant vesting fully on grant and another vesting on February 20, 2026. The phantom units and RSUs are payable or settled in common shares upon the reporting person’s separation from service.

Positive

• Continued indirect ownership via foundation, LLC, and trust (14,920; 69,440; 12,054 shares) preserves long-term alignment
• Deferred equity (RSUs and phantom stock) remain structured to settle in common shares, aligning pay with shareholder value

Negative

• Large disposition of 68,953 common shares on 10/01/2025 reduces the reporting person’s direct stake
• Significant portion of holdings indirect or contingent on separation dates, limiting immediate voting influence from those instruments

Insights

Insider Transactions Analyst

TL;DR: Director sold a large block and retains several indirect and deferred equity holdings.

The Form 4 records a disposition of 68,953 common shares on 10/01/2025, while the reporting person continues to have indirect ownership through a foundation, LLC, and trust totaling 95,?414 shares across those entities as reported individually. The filing also shows 872 phantom units and RSUs that convert to common shares upon separation, with one RSU vesting on February 20, 2026. This mix indicates liquidity was realized via the sale while material deferred compensation remains tied to future service or separation events.

Corporate Governance Expert

TL;DR: Disclosure clarifies types of holdings and settlement conditions for deferred awards.

The filing differentiates direct, indirect, and derivative-like holdings: direct dispositions, indirect holdings by a foundation/LLC/trust, RSUs with specified vesting, and phantom stock payable on separation. These distinctions matter for understanding when economic exposure converts to voting shares and when payouts may occur. The filing’s explanations explicitly state settlement occurs in common stock upon separation, and one RSU tranche vests on February 20, 2026.

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^*

HOLCOMBE GREGORY F

(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)
10/01/2025

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								68,953(1)(2)	D
Common Stock								14,920	I	By Foundation
Common Stock								69,440	I	By LLC
Common Stock								12,054	I	By Trust

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)	10/01/2025		A		$872		(3)	(3)	Common Stock	872	$25.1	22,061	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	10/03/2025
	** 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 did Gregory F. Holcombe report on Form 4 for OBT?

The report shows a disposition of 68,953 common shares on 10/01/2025 and lists various indirect holdings and deferred equity instruments.

How many phantom stock units and RSUs does the filing disclose?

The filing discloses 872 phantom stock units and RSUs that include one tranche vesting February 20, 2026 plus other RSUs that vest 100% as of grant and settle upon separation.

What indirect holdings does Holcombe report for OBT?

Indirect holdings reported are 14,920 shares by a foundation, 69,440 shares by an LLC, and 12,054 shares by a trust.

Do the deferred awards convert to common stock?

Yes. The filing states RSUs and phantom stock are settled or become payable in shares of common stock upon the reporting person’s separation from service.

When did the reported transaction occur?

The transaction date shown in the filing is 10/01/2025.