Dimitar Karaivanov - Mar 14, 2023 Form 4 Insider Report for COMMUNITY BANK SYSTEM, INC. (CBU)

Role: EVP, Chief Operating Officer
Signature: /s/ Danielle M. Cima, pursuant to a Confirming Statement executed by Dimitar Karaivanov
Stock symbol: CBU
Transactions as of: Mar 14, 2023
Transactions value $: $0
Form type: 4
Date filed: 3/15/2023, 11:18 AM
Previous filing: Mar 9, 2023
Next filing: Mar 28, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	CBU	Common Stock	Award	$0	+2.35K	+18.51%	$0.00	15K	Mar 14, 2023	Direct
holding	CBU	Common Stock						334	Mar 14, 2023	By 401(k) Plan

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	CBU	Stock Option	Award	$0	+8.56K		$0.00	8.56K	Mar 14, 2023	Common Stock	8.56K	$54.06	Direct	F1

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	The option vests ratably on March 14, 2024, 2025, 2026, 2027, and 2028.