OBT

SEC source: 0001437749-25-007329 · rdgdoc.xml · nonDerivative · entry 1

Sousa Gregory · CIK 0001875279 · EVP and Deputy CLO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,669

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F5 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-007314 · rdgdoc.xml · nonDerivative · entry 1

Rooney Stephen · CIK 0001464333 · SVP, Chief Credit Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,217

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on November 8, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-007321 · rdgdoc.xml · nonDerivative · entry 1

Gilfeather Michael J · CIK 0001333208 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 89,088

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F2 · balance_after: Includes restricted stock units which vest on December 31, 2026.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F5 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-007325 · rdgdoc.xml · nonDerivative · entry 1

Dineen David P · CIK 0001681144 · SVP, Dir. Wealth Services

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,712

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on May 28, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-007307 · rdgdoc.xml · nonDerivative · entry 1

Jones Elizabeth A · CIK 0001915399 · SVP, Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,830

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F3 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004779 · rdgdoc.xml · nonDerivative · entry 1

Keane Kevin J · CIK 0001907910 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,497

F5 · shares: 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.

F1 · balance_after: 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.

F2 · balance_after: Includes restricted stock units which vest 100% on March 21, 2025 and are settled in shares of Issuer common stock upon separation from service of the reporting person.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004777 · rdgdoc.xml · nonDerivative · entry 1

Schiller Jon · CIK 0002040355 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,995

F3 · shares: 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.

F2 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004764 · rdgdoc.xml · nonDerivative · entry 1

Rouis Jonathan F · CIK 0001875271 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,397

F5 · shares: 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.

F1 · balance_after: 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.

F2 · balance_after: Includes restricted stock units which vest 100% on March 21, 2025 and are settled in shares of Issuer common stock upon separation from service of the reporting person.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004770 · rdgdoc.xml · derivative · entry 3

Sousa Gregory · CIK 0001875279 · EVP and Deputy CLO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,601

Underlying: Common Stock · 1,223 shares

Expires not disclosed

F5 · derivative.exercise_price: 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.

F5 · derivative.exercise_date: 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.

F5 · derivative.expiration_date: 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.

F6 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004781 · rdgdoc.xml · nonDerivative · entry 1

Morrison William D · CIK 0001875297 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 103,741

F4 · shares: 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.

F1 · balance_after: 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.

F2 · balance_after: Includes restricted stock units which vest 100% on March 21, 2025 and are settled in shares of Issuer common stock upon separation from service of the reporting person.

F3 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004772 · rdgdoc.xml · nonDerivative · entry 1

HOLCOMBE GREGORY F · CIK 0001191186 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 70,055

F5 · shares: 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.

F1 · balance_after: 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.

F2 · balance_after: Includes restricted stock units which vest 100% on March 21, 2025 and are settled in shares of Issuer common stock upon separation from service of the reporting person.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004774 · rdgdoc.xml · derivative · entry 3

Gilfeather Michael J · CIK 0001333208 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21.572

Underlying: Common Stock · 4,817 shares

Expires not disclosed

F5 · derivative.exercise_price: 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.

F5 · derivative.exercise_date: 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.

F5 · derivative.expiration_date: 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.

F6 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004768 · rdgdoc.xml · nonDerivative · entry 1

Rowley Richard B · CIK 0001370312 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 538,365

F5 · shares: 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.

F1 · balance_after: 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.

F2 · balance_after: Includes restricted stock units which vest 100% on March 21, 2025 and are settled in shares of Issuer common stock upon separation from service of the reporting person.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004766 · rdgdoc.xml · derivative · entry 4

Lesler Michael · CIK 0001393132 · EVP, Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 882

Underlying: Common Stock · 882 shares

Expires not disclosed

F6 · derivative.exercise_price: 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.

F6 · derivative.exercise_date: 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.

F6 · derivative.expiration_date: 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 source: 0001437749-25-004783 · rdgdoc.xml · nonDerivative · entry 1

Kennedy Marianna R · CIK 0001947963 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,697

F5 · shares: 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

F1 · balance_after: 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.

F2 · balance_after: Includes restricted stock units which vest 100% on March 21, 2025 and are settled in shares of Issuer common stock upon separation from service of the reporting person.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004762 · rdgdoc.xml · nonDerivative · entry 1

Tirado Olga Luz · CIK 0001995774 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,097

F4 · shares: 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.

F1 · balance_after: Includes restricted stock units which vest 100% on March 21, 2025 and are settled in shares of Issuer common stock upon separation from service of the reporting person.

F3 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004575 · rdgdoc.xml · nonDerivative · entry 1

Listner Michael · CIK 0001876359 · SVP and Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,808

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004582 · rdgdoc.xml · nonDerivative · entry 1

Coulter Michael J · CIK 0001875275 · EVP and CLO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,607

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F5 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004573 · rdgdoc.xml · nonDerivative · entry 1

Ruhl Joseph A · CIK 0001875278 · Reg Pres, Westchester County

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 28,426

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004584 · rdgdoc.xml · nonDerivative · entry 1

Sousa Gregory · CIK 0001875279 · EVP and Deputy CLO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,079

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F6 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004580 · rdgdoc.xml · nonDerivative · entry 1

Gilfeather Michael J · CIK 0001333208 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 90,704

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest on December 31, 2026.

F4 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F6 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004578 · rdgdoc.xml · nonDerivative · entry 1

Jones Elizabeth A · CIK 0001915399 · SVP, Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,083

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-007304 · rdgdoc.xml · nonDerivative · entry 1

Jones Elizabeth A · CIK 0001915399 · SVP, Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,083

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F4 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-004255 · rdgdoc.xml · nonDerivative · entry 1

Gilfeather Michael J · CIK 0001333208 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 91,837

F3 · shares: Includes restricted stock units which vest on December 31, 2026.

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest on December 31, 2026.

F4 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

F6 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-002022 · rdgdoc.xml · derivative · entry 2

Rowley Richard B · CIK 0001370312 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,065

Underlying: Common Stock · 58 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

F2 · balance_after: Restricted stock units which vested 100% on August 8, 2024 (including accumulated dividends) and were deferred into the Orange County Bancorp, Inc. Stock-Based Deferral Plan, as amended and restated. The restricted stock units will settle in shares of Issuer common stock upon the reporting person's separation from service.

F5 · balance_after: Reflects two-for-one forward stock split of the Issuer's common stock which occurred on January 10, 2025.

SEC source: 0001437749-25-000255 · rdgdoc.xml · derivative · entry 4

Keane Kevin J · CIK 0001907910 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,498

Underlying: Common Stock · 358 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001437749-25-000241 · rdgdoc.xml · derivative · entry 2

Schiller Jon · CIK 0002040355 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 358

Underlying: Common Stock · 358 shares

Expires not disclosed

F1 · derivative.exercise_price: 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.

F1 · derivative.exercise_date: 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.

F1 · derivative.expiration_date: 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.

SEC source: 0001437749-25-000239 · rdgdoc.xml · derivative · entry 3

Rouis Jonathan F · CIK 0001875271 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,585

Underlying: Common Stock · 83 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001437749-25-000257 · rdgdoc.xml · derivative · entry 5

HOLCOMBE GREGORY F · CIK 0001191186 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,542

Underlying: Common Stock · 405 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001437749-25-000240 · rdgdoc.xml · derivative · entry 2

Rowley Richard B · CIK 0001370312 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,542

Underlying: Common Stock · 405 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001437749-25-000261 · rdgdoc.xml · derivative · entry 2

Tirado Olga Luz · CIK 0001995774 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23

Underlying: Common Stock · 23 shares

Expires not disclosed

F2 · derivative.exercise_price: 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.

F2 · derivative.exercise_date: 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.

F2 · derivative.expiration_date: 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.

SEC source: 0001437749-25-002021 · rdgdoc.xml · derivative · entry 3

Gilfeather Michael J · CIK 0001333208 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,378

Underlying: Common Stock · 223 shares

Expires not disclosed

F5 · derivative.exercise_price: 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.

F5 · derivative.exercise_date: 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.

F5 · derivative.expiration_date: 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.

SEC source: 0001437749-24-038348 · rdgdoc.xml · nonDerivative · entry 1

Lesler Michael · CIK 0001393132 · EVP, Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,736

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on December 23, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

SEC source: 0001437749-24-037863 · rdgdoc.xml · derivative · entry 4

Keane Kevin J · CIK 0001907910 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,140

Underlying: Common Stock · 22 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001437749-24-037859 · rdgdoc.xml · derivative · entry 3

Rouis Jonathan F · CIK 0001875271 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,503

Underlying: Common Stock · 6 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001437749-24-037869 · rdgdoc.xml · derivative · entry 3

Sousa Gregory · CIK 0001875279 · EVP and Deputy CLO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,189

Underlying: Common Stock · 5 shares

Expires not disclosed

F5 · derivative.exercise_price: 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.

F5 · derivative.exercise_date: 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.

F5 · derivative.expiration_date: 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 source: 0001437749-24-037865 · rdgdoc.xml · derivative · entry 5

HOLCOMBE GREGORY F · CIK 0001191186 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,137

Underlying: Common Stock · 34 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001437749-24-037867 · rdgdoc.xml · derivative · entry 3

Gilfeather Michael J · CIK 0001333208 · Director · President and CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,154

Underlying: Common Stock · 34 shares

Expires not disclosed

F5 · derivative.exercise_price: 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.

F5 · derivative.exercise_date: 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.

F5 · derivative.expiration_date: 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.

SEC source: 0001437749-24-037856 · rdgdoc.xml · derivative · entry 2

Rowley Richard B · CIK 0001370312 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,137

Underlying: Common Stock · 34 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001437749-24-037861 · rdgdoc.xml · derivative · entry 2

Kennedy Marianna R · CIK 0001947963 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,208

Underlying: Common Stock · 13 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001437749-25-002009 · rdgdoc.xml · derivative · entry 4

Keane Kevin J · CIK 0001907910 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,601

Underlying: Common Stock · 24 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

F2 · balance_after: Restricted stock units which vested 100% on August 8, 2024 (including accumulated dividends) and were deferred into the Orange County Bancorp, Inc. Stock-Based Deferral Plan, as amended and restated. The restricted stock units will settle in shares of Issuer common stock upon the reporting person's separation from service.

SEC source: 0001437749-25-001996 · rdgdoc.xml · derivative · entry 3

Rouis Jonathan F · CIK 0001875271 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,964

Underlying: Common Stock · 8 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

F2 · balance_after: Restricted stock units which vested 100% on August 8, 2024 (including accumulated dividends) and were deferred into the Orange County Bancorp, Inc. Stock-Based Deferral Plan, as amended and restated. The restricted stock units will settle in shares of Issuer common stock upon the reporting person's separation from service.

SEC source: 0001437749-25-002015 · rdgdoc.xml · derivative · entry 5

HOLCOMBE GREGORY F · CIK 0001191186 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,598

Underlying: Common Stock · 36 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

F2 · balance_after: Includes restricted stock units which vested 100% on August 8, 2024 (including accumulated dividends) and are settled in shares of Issuer common stock upon separation from service of the reporting person.

SEC source: 0001437749-25-001990 · rdgdoc.xml · derivative · entry 2

Rowley Richard B · CIK 0001370312 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,598

Underlying: Common Stock · 36 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

F2 · balance_after: Restricted stock units which vested 100% on August 8, 2024 (including accumulated dividends) and were deferred into the Orange County Bancorp, Inc. Stock-Based Deferral Plan, as amended and restated. The restricted stock units will settle in shares of Issuer common stock upon the reporting person's separation from service.

SEC source: 0001437749-25-002002 · rdgdoc.xml · derivative · entry 2

Kennedy Marianna R · CIK 0001947963 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,670

Underlying: Common Stock · 15 shares

Expires not disclosed

F4 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

F2 · balance_after: Restricted stock units which vested 100% on August 8, 2024 (including accumulated dividends) and were deferred into the Orange County Bancorp, Inc. Stock-Based Deferral Plan, as amended and restated. The restricted stock units will settle in shares of Issuer common stock upon the reporting person's separation from service.

SEC source: 0001437749-24-036699 · rdgdoc.xml · nonDerivative · entry 1

Rooney Stephen · CIK 0001464333 · SVP, Chief Credit Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,175

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on November 8, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

SEC source: 0001437749-24-036039 · rdgdoc.xml · nonDerivative · entry 1

Ruhl Joseph A · CIK 0001875278 · Reg Pres, Westchester County

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,464

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025

SEC source: 0001437749-24-034467 · rdgdoc.xml · nonDerivative · entry 1

Rooney Stephen · CIK 0001464333 · SVP, Chief Credit Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,875

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on November 8, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

SEC source: 0001437749-24-033838 · rdgdoc.xml · nonDerivative · entry 2

Listner Michael · CIK 0001876359 · SVP and Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,072

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

SEC source: 0001437749-24-033838 · rdgdoc.xml · nonDerivative · entry 1

Listner Michael · CIK 0001876359 · SVP and Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,286

F1 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on February 15, 2023.

F2 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

F3 · balance_after: Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.