Orange County Bancorp CEO gets stock awards, buys shares

Orange County Bancorp President and CEO Michael J. Gilfeather reported mainly compensation-related equity activity.

Rhea-AI Filing Summary

Orange County Bancorp President and CEO Michael J. Gilfeather reported mainly compensation-related equity activity. He received two Common Stock awards of 16,853 and 9,438 shares at no cost, increasing his direct holdings before taxes. To cover tax obligations, 6,189 shares were withheld at a price of $31.15 per share, leaving him with 129,449 directly held shares, including restricted stock units that vest over several future dates. He also made a small open-market purchase of 200 Common Stock shares in an IRA at $31.2499 per share, bringing that indirect IRA position to 16,400 shares. In addition, he holds 26,460 phantom stock units, each economically equivalent to one share of Common Stock, payable upon his separation from service as a director.

Insider Trade Summary

Net Buyer: 200 shares

Net Buy 5 txns

Insider Gilfeather Michael J

Role President and CEO

Bought 200 shs ($6K)

Type	Security	Shares	Price	Value
Grant/Award	Common Stock	16,853	$0.00	$0.00
Grant/Award	Common Stock	9,438	$0.00	$0.00
Exercise Price or Tax Liability	Common Stock	6,189	$31.15	$193K
Purchase	Common Stock	200	$31.2499	$6K
holding	Phantom Stock	--	--	--

Holdings After Transaction: Common Stock — 129,449 shares (Direct); Common Stock — 16,400 shares (Indirect, By IRA); Phantom Stock — 26,460 contracts (Direct)

Footnotes (6)

1. F1. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.
2. F2. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 20, 2026.
3. F3. Includes restricted stock units which vest on December 31, 2026.
4. F4. Restricted stock units which vest at a rate of 1/3 per year commencing on March 19, 2027.
5. F5. Restricted stock units which vest on March 19, 2029.
6. F6. 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.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What stock transactions did OBT CEO Michael J. Gilfeather report on March 19, 2026?

He reported stock awards, tax withholding, and a small purchase. Two Common Stock grants totaled 26,291 shares, 6,189 shares were withheld for taxes, and 200 shares were bought in an IRA, reflecting mainly compensation-related activity with a modest personal purchase.

How many Orange County Bancorp (OBT) shares does the CEO hold after these transactions?

After these transactions, Michael J. Gilfeather directly holds 129,449 Common Stock shares. This figure includes restricted stock units scheduled to vest over several future dates, reflecting his ongoing equity-based compensation and long-term alignment with Orange County Bancorp shareholders.

What price did the OBT CEO pay for his March 19, 2026 share purchase?

He purchased 200 Common Stock shares at $31.2499 per share in an IRA. This open-market transaction increased his indirect IRA holdings to 16,400 shares, complementing his larger, compensation-based direct equity position in Orange County Bancorp.

Why were 6,189 Orange County Bancorp shares disposed of in this Form 4?

The 6,189-share disposition was a tax-withholding transaction at $31.15 per share. Shares were withheld to cover tax obligations associated with equity awards, rather than sold in the open market, so it does not represent a discretionary sale of stock.

What are the vesting terms of the CEO’s restricted stock units at OBT?

His restricted stock units vest under several schedules. Some vest one-third per year starting March 21, 2025, others from March 20, 2026 and March 19, 2027, while additional units fully vest on December 31, 2026 and March 19, 2029, supporting long-term incentives.

What phantom stock holdings does the Orange County Bancorp CEO report?

He reports 26,460 phantom stock units, each economically equivalent to one Common Stock share. These units become payable when he separates from service as a director, providing deferred, share-linked compensation tied to Orange County Bancorp’s equity value over time.

AI-generated analysis. How Rhea-AI works. Not financial advice.

Form 4 Insider Transactions: What Each Field Means →

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Accepted by SEC EDGAR 03/23/2026 - 05:42 PM Learn about SEC filing dates

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 NEW YORK 10940

(City) (State) (Zip)

UNITED STATES

(Country)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
03/19/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	03/19/2026		A		16,853(4)	A	$0	126,200(1)(2)(3)	D
Common Stock	03/19/2026		A		9,438(5)	A	$0	135,638(1)(2)(3)	D
Common Stock	03/19/2026		F		6,189	D	$31.15	129,449(1)(2)(3)	D
Common Stock	03/19/2026		P		200	A	$31.2499	16,400	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	(6)							(6)	(6)	Common Stock	26,460		26,460	D

Explanation of Responses:

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

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

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

4. Restricted stock units which vest at a rate of 1/3 per year commencing on March 19, 2027.

5. Restricted stock units which vest on March 19, 2029.

6. 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	03/23/2026
	** 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.
* Form 4: SEC 1474 (03-26)