Award4

Orange County Bancorp, Inc. /DE/

Total Value

Filing Date

Sep 16, 2026

1 transactions

Trade Summary

On Sep 15, 2026, Lesler Michael, EVP, Chief Financial Officer, reported $0 of Orange County Bancorp, Inc. /DE/ (OBT) across 1 transactions. The filing covers company securities and reflects balanced net activity of $0. Insider transactions are sourced from SEC Form 4 disclosures and should be reviewed alongside company fundamentals and the insider's broader trading history.

Insider Information

Name: Lesler Michael
Role: EVP, Chief Financial Officer
Location: MIDDLETOWN, NY

Filing Details

Filing Date: Sep 16, 2026
Transaction Date: Sep 15, 2026
Accession Number: 0001437749-26-030567
Form Type: 4

Derivative Transactions

Date	Security	Shares	Exercise Price	Type	Value
Sep 15, 2026	OBT derivative	—	—	Grant/Award	—

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Footnotes

(F1)Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.
(F2)Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 20, 2026.
(F3)Restricted stock units which vest at a rate of 1/3 per year commencing on March 19, 2027.
(F4)Reflects transactions not required to be reported pursuant to Section 16 of the Securities Exchange Act of 1934, as amended.
(F5)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.

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^*

Lesler Michael

(Last)

(First)

(Middle)

212 DOLSON AVENUE

(Street)

MIDDLETOWN

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)
09/15/2026

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock								16,216⁽¹⁾⁽²⁾⁽³⁾	D
Common Stock								1,623⁽⁴⁾	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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Phantom Stock	⁽⁵⁾	09/15/2026		A		$12		⁽⁵⁾	⁽⁵⁾	Common Stock	12	$38.78	2,543	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. Restricted stock units which vest at a rate of 1/3 per year commencing on March 19, 2027.

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

5. 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	09/16/2026
	** 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 as rendered by the SEC from accession 0001437749-26-030567.

Orange County Bancorp, Inc. /DE/

Trade Summary

Company Information

Insider Information

Filing Details

Derivative Transactions

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Footnotes

SEC Form 4

SEC Filing

SEC Form 4