CBU

SEC source: 0001127602-23-010115 · form4.xml · nonDerivative · entry 1

ACE BRIAN R · CIK 0001264817 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 63,493.6029

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-23-009553 · form4.xml · nonDerivative · entry 1

LEVY JEFFREY M · CIK 0001384972 · President, Commercial Banking

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,410

F1 · kind: Payment of tax liability associated with vesting of restricted stock award.

SEC source: 0001127602-23-009550 · form4.xml · nonDerivative · entry 1

Abdo Michael N · CIK 0001933852 · EVP and General Counsel

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,495

F1 · kind: Payment of tax liability associated with vesting of restricted stock award.

SEC source: 0001127602-23-009549 · form4.xml · nonDerivative · entry 1

Gillan-Myer Maureen A · CIK 0001670754 · EVP, Chief Human Resources Off

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,849

F1 · kind: Payment of tax liability associated with vesting of restricted stock award.

SEC source: 0001127602-23-009548 · form4.xml · nonDerivative · entry 1

SUTARIS JOSEPH E · CIK 0001278835 · EVP & Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,913.9958

F1 · kind: Payment of tax liability associated with vesting of restricted stock awards.

SEC source: 0001127602-23-009547 · form4.xml · nonDerivative · entry 1

Karaivanov Dimitar · CIK 0001866135 · EVP, Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,687

F1 · kind: Payment of tax liability associated with vesting of restricted stock award.

SEC source: 0001127602-23-009546 · form4.xml · nonDerivative · entry 1

TRYNISKI MARK E · CIK 0001242753 · Director · President & CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 29,711

F1 · kind: Payment of tax liability associated with the vesting of restricted stock awards.

SEC source: 0001127602-23-008716 · form4.xml · derivative · entry 12

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 468

Underlying: Common Stock · 4,163 shares

Expires 2023-03-19

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-23-008716 · form4.xml · nonDerivative · entry 2

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 85,153.062

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $60.50 to $60.5623, inclusive. The reporting person undertakes to provide Community Bank System, Inc., any security holder of Community Bank System, Inc. or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001127602-23-008716 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 89,316.062

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · balance_after: Includes 1,687.6874 shares acquired pursuant to the Community Bank System, Inc. Dividend Reinvestment Plan.

SEC source: 0001127602-23-008666 · form4.xml · derivative · entry 5

ACE BRIAN R · CIK 0001264817 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 483

Underlying: Common Stock · 4,148 shares

Expires 2023-03-19

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-23-008666 · form4.xml · nonDerivative · entry 3

ACE BRIAN R · CIK 0001264817 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 63,010.6029

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $60.5003 to $60.5623, inclusive. The reporting person undertakes to provide Community Bank System, Inc., any security holder of Community Bank System, Inc. or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001127602-23-008666 · form4.xml · nonDerivative · entry 2

ACE BRIAN R · CIK 0001264817 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 67,158.6029

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-23-003520 · form4.xml · nonDerivative · entry 1

ACE BRIAN R · CIK 0001264817 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 70,423.6029

SEC source: 0001127602-23-001849 · form4.xml · derivative · entry 2

Fesette Neil E. · CIK 0001485738 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 7,071.9751

Underlying: Common Stock · 633.3678 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F2 · balance_after: Includes 47.4236, 50.8174, 54.984, and 52.5636 units of phantom stock acquired on April 11, 2022, July 11, 2022, October 10, 2022, and January 10, 2023, respectively, under the Deferred Compensation Plan's dividend reinvestment feature.

SEC source: 0001127602-23-001849 · form4.xml · nonDerivative · entry 1

Fesette Neil E. · CIK 0001485738 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,585.8069

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-23-000373 · form4.xml · derivative · entry 3

ACE BRIAN R · CIK 0001264817 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,217.1164

Underlying: Common Stock · 3,354.6029 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F2 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F2 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

SEC source: 0001127602-23-000373 · form4.xml · nonDerivative · entry 1

ACE BRIAN R · CIK 0001264817 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 71,423.6029

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: On January 3, 2023, the reporting person's phantom stock units were settled for an equal number of shares of Community Bank System, Inc. common stock.

SEC source: 0001127602-23-000322 · form4.xml · derivative · entry 3

STEELE SALLY A · CIK 0001264816 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 6,526.0997

Underlying: Common Stock · 3,366.0319 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F2 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F2 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F3 · balance_after: Includes 69.0288, 73.4281, and 77.8631 units of phantom stock acquired on April 9, 2021, July 9, 2021 and October 8, 2021, respectively under the Deferred Compensation Plan's dividend reinvestment feature.

SEC source: 0001127602-23-000322 · form4.xml · nonDerivative · entry 1

STEELE SALLY A · CIK 0001264816 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 42,372.2727

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: On January 3, 2023, the reporting person's phantom stock units were settled for an equal number of shares of Community Bank System, Inc. common stock.

SEC source: 0001127602-23-000774 · form4.xml · derivative · entry 5

DAVIS JEFFREY L · CIK 0001220435 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 50,488.2253

Underlying: Common Stock · 7,521 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: The units of phantom stock were acquired through Merchants deferred compensation plan. Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to such deferred compensation plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F3 · derivative.exercise_date: The units of phantom stock were acquired through Merchants deferred compensation plan. Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to such deferred compensation plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F3 · derivative.expiration_date: The units of phantom stock were acquired through Merchants deferred compensation plan. Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to such deferred compensation plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

SEC source: 0001127602-23-000774 · form4.xml · nonDerivative · entry 1

DAVIS JEFFREY L · CIK 0001220435 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 21,516

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: On January 3, 2023, the reporting person's phantom stock units acquired under the Merchants Bancshares, Inc. ("Merchants") deferred compensation plan were settled for an equal number of shares of Community Bank System, Inc. common stock.

SEC source: 0001127602-23-008666 · form4.xml · nonDerivative · entry 1

ACE BRIAN R · CIK 0001264817 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 59,737

F1 · kind: Gift to charitable trust.

F2 · balance_after: Includes 919 shares acquired pursuant to the Community Bank System, Inc. Dividend Reinvestment Plan.

SEC source: 0001127602-22-027800 · form4.xml · derivative · entry 1

Pecor Raymond C III · CIK 0001475265 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 4,564.43

Underlying: Common Stock · 342.9815 shares

Expires not disclosed

F1 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

SEC source: 0001127602-22-027799 · form4.xml · derivative · entry 1

DAVIS JEFFREY L · CIK 0001220435 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,983.4303

Underlying: Common Stock · 355.5295 shares

Expires not disclosed

F1 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

SEC source: 0001127602-22-027798 · form4.xml · derivative · entry 11

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 632.6587

Underlying: Common Stock · 590.6526 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive Plan (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Bank System, Inc. common stock and will be settled in common stock at a predetermined date.

F1 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive Plan (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Bank System, Inc. common stock and will be settled in common stock at a predetermined date.

F1 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive Plan (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Bank System, Inc. common stock and will be settled in common stock at a predetermined date.

SEC source: 0001127602-22-027798 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 83,465.3746

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-22-026946 · form4.xml · derivative · entry 4

SUTARIS JOSEPH E · CIK 0001278835 · EVP & Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,388 shares

Expires 2025-03-18

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_date: The option vests ratably on March 18, 2016, 2017, 2018, 2019 and 2020.

SEC source: 0001127602-22-026946 · form4.xml · nonDerivative · entry 2

SUTARIS JOSEPH E · CIK 0001278835 · EVP & Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 9,449.9958

SEC source: 0001127602-22-026946 · form4.xml · nonDerivative · entry 1

SUTARIS JOSEPH E · CIK 0001278835 · EVP & Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,262.9958

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001104659-22-124644 · tm2232051-1_4seq1.xml · derivative · entry 2

Whipple John F. · CIK 0001485739 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,605.3237

Underlying: Common Stock · 1,225.1412 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F2 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F2 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

SEC source: 0001104659-22-124644 · tm2232051-1_4seq1.xml · nonDerivative · entry 1

Whipple John F. · CIK 0001485739 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,855.6272

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: On December 1, 2022, the reporting person's phantom stock units were settled for an equal number of shares of Community Bank System, Inc. common stock.

SEC source: 0001127602-22-025896 · form4.xml · derivative · entry 3

STICKELS ERIC · CIK 0001201821 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,169.0591

Underlying: Common Stock · 525.4672 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive Plan (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Bank System, Inc. common stock and will be settled in common stock at a predetermined date.

F1 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive Plan (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Bank System, Inc. common stock and will be settled in common stock at a predetermined date.

F1 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive Plan (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Bank System, Inc. common stock and will be settled in common stock at a predetermined date.

SEC source: 0001127602-22-025896 · form4.xml · nonDerivative · entry 1

STICKELS ERIC · CIK 0001201821 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 33,269.4672

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-22-023928 · form4.xml · nonDerivative · entry 2

Serbun Joseph F · CIK 0001741822 · President, Retail Banking

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,245.6573

F2 · shares: Granted pursuant to the Retirement and Release Agreement filed as Exhibit 10.2 to Community Bank System's Current Report on Form 8-K filed with the Securities and Exchange Commission on August 26, 2022.

SEC source: 0001127602-22-023884 · form4.xml · nonDerivative · entry 1

Gillan-Myer Maureen A · CIK 0001670754 · EVP, Chief Human Resources Off

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,930

F1 · kind: Payment of tax liability associated with vesting of restricted stock award.

SEC source: 0001127602-22-023928 · form4.xml · nonDerivative · entry 1

Serbun Joseph F · CIK 0001741822 · President, Retail Banking

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,762.6573

F1 · kind: Payment of tax liability associated with vesting of restricted stock award.

SEC source: 0001127602-22-022876 · form4.xml · derivative · entry 1

Pecor Raymond C III · CIK 0001475265 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 4,221.4485

Underlying: Common Stock · 297.8494 shares

Expires not disclosed

F1 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

SEC source: 0001127602-22-022875 · form4.xml · derivative · entry 1

DAVIS JEFFREY L · CIK 0001220435 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,627.9008

Underlying: Common Stock · 309.4538 shares

Expires not disclosed

F1 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

SEC source: 0001127602-22-021420 · form4.xml · nonDerivative · entry 1

STEELE SALLY A · CIK 0001264816 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 39,006.2408

SEC source: 0001127602-22-017748 · form4.xml · derivative · entry 1

Pecor Raymond C III · CIK 0001475265 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,923.5991

Underlying: Common Stock · 307.3117 shares

Expires not disclosed

F1 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

SEC source: 0001127602-22-017747 · form4.xml · derivative · entry 1

DAVIS JEFFREY L · CIK 0001220435 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,318.447

Underlying: Common Stock · 319.2848 shares

Expires not disclosed

F1 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

F1 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Bank System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Bank System, Inc. common stock at future dates selected by the reporting person.

SEC source: 0001127602-22-017034 · form4.xml · nonDerivative · entry 1

Karaivanov Dimitar · CIK 0001866135 · EVP Financial Serv & Corp Dev

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,204

SEC source: 0001127602-22-015351 · form4.xml · nonDerivative · entry 1

STEELE SALLY A · CIK 0001264816 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 39,506.2408

SEC source: 0001127602-22-012744 · form4.xml · nonDerivative · entry 1

MacPherson Kerrie D. · CIK 0001794595 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,662

SEC source: 0001127602-22-012707 · form4.xml · nonDerivative · entry 1

STEELE SALLY A · CIK 0001264816 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 41,506.2408

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $66.25 to $67.00, inclusive. The reporting person undertakes to provide Community Bank System, Inc., any security holder of Community Bank System, Inc. or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

SEC source: 0001127602-22-012123 · form4.xml · derivative · entry 3

STEELE SALLY A · CIK 0001264816 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 644.1178

Underlying: Common Stock · 582.4868 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive Plan (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Bank System, Inc. common stock and will be settled in common stock at a predetermined date.

F1 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive Plan (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Bank System, Inc. common stock and will be settled in common stock at a predetermined date.

F1 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive Plan (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Bank System, Inc. common stock and will be settled in common stock at a predetermined date.

SEC source: 0001127602-22-012123 · form4.xml · nonDerivative · entry 1

STEELE SALLY A · CIK 0001264816 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 51,506.2408

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001127602-22-010644 · form4.xml · derivative · entry 6

LEVY JEFFREY M · CIK 0001384972 · President, Commercial Banking

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,705

Underlying: Common Stock · 568 shares

Expires 2030-03-17

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F4 · derivative.exercise_date: The option vested ratably on March 17, 2021, 2022, 2023, 2024 and 2025.

SEC source: 0001127602-22-010644 · form4.xml · derivative · entry 5

LEVY JEFFREY M · CIK 0001384972 · President, Commercial Banking

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 772

Underlying: Common Stock · 386 shares

Expires 2029-03-20

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_date: The option vested ratably on March 20, 2020, 2021, 2022, 2023 and 2024.