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

Rhea-AI Filing Summary

Insider filing: Michael Lesler, EVP and Chief Financial Officer of Orange County Bancorp, Inc. (OBT), reported changes in his beneficial ownership on Form 4. The filing shows a disposition of 12,845 shares of common stock and continued indirect holdings of 1,062 shares in a 401(k) and 2,000 shares in an IRA. The report also records the acquisition of phantom stock interests tied to the company’s Performance-Based SERP representing 4 underlying shares with a stated price of $25.95; those phantom interests may be settled in company stock upon distribution based on prior election. Several disclosed restricted stock unit grants vest in thirds on various commencement dates in 2023–2026.

Positive

• Retention of equity-linked compensation: Multiple restricted stock unit grants with scheduled vesting through 2026 indicate continuing incentive alignment with shareholders
• Performance-based deferred pay: Phantom stock under the Performance-Based SERP may settle in shares, linking future compensation to company performance

Negative

• Direct disposition of 12,845 shares: The CFO sold a material number of shares directly, reducing his direct beneficial ownership

Insights

Financial Analyst

TL;DR: Insider sale of 12,845 shares with ongoing retirement-plan holdings and performance-based phantom stock grants; no exercise of listed options.

The filing details a direct sale of 12,845 common shares by the CFO and records indirect holdings via a 401(k) and IRA totaling 3,062 shares. It also documents phantom stock credits under a Performance-Based SERP for 4 underlying shares at $25.95, which are a deferred, performance-linked compensation mechanism potentially settled in stock. Multiple restricted stock unit awards are noted with staggered vesting schedules through 2026, indicating ongoing equity compensation rather than market-driven option exercises.

Corporate Governance Expert

TL;DR: Transaction mix reflects routine executive compensation and a discretionary disposal; disclosures conform to Section 16 reporting requirements.

The disclosure identifies the reporting person as an officer and director-level executive, lists a sale of common stock and the grant/accrual of deferred phantom stock under the SERP, and clarifies vesting schedules for several RSU grants. The presence of retirement-account holdings and performance-based phantom awards suggests standard compensation structuring. The report was executed via power of attorney, which is a common administrative practice for timely Section 16 filings.

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^*

Lesler Michael

(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)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	EVP, Chief Financial Officer

3. Date of Earliest Transaction (Month/Day/Year)
09/16/2025

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								12,845(1)(2)(3)(4)	D
Common Stock								1,062(5)	I	By 401(k)
Common Stock								2,000	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)	09/16/2025		A		$4		(6)	(6)	Common Stock	4	$25.95	896	D

Explanation of Responses:

1. Includes restricted stock units which vest at a rate of 1/3 per year commencing on December 23, 2023.

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

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. Reflects transactions not required to be reported pursuant to Section 16 of the Securities Exchange Act of 1934, as amended.

6. Represents deemed investments in connection with the Performance-Based SERP. Phantom stock interests under the Performance-Based SERP may be settled in shares of Company stock upon distribution to the reporting person, based on their prior election.

	/s/ Jennifer Staub, pursuant to power of attorney	09/17/2025
	** 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).
** 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 Michael Lesler report on the Form 4 for OBT?

The filing reports a disposition of 12,845 common shares, indirect holdings of 1,062 shares in a 401(k) and 2,000 shares in an IRA, plus acquisition of phantom stock interests tied to the Performance-Based SERP.

Did the Form 4 show any stock option exercises for OBT?

No option exercises are reported; the filing shows RSUs, indirect retirement-plan holdings, and phantom stock interests rather than exercised derivative securities.

How many phantom shares were acquired and at what price?

The report records phantom stock interests representing 4 underlying shares with a stated price of $25.95 associated with the Performance-Based SERP.

Are there vesting schedules disclosed in the Form 4?

Yes; the filing lists several restricted stock unit grants that vest at a rate of 1/3 per year beginning on dates in December 23, 2023; March 11, 2024; March 21, 2025; and March 20, 2026.

Was the Form 4 filed by the reporting person directly?

The signature block indicates the form was signed by Jennifer Staub pursuant to power of attorney on 09/17/2025.