Bolus Mark J.

SEC source: 0000723188-26-000104 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 94,060

SEC source: 0000723188-26-000064 · form4.xml · derivative · entry 7

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,758.2915

Underlying: Common Stock · 1,220 shares

Expires not disclosed

F4 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "LTIP"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F4 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "LTIP"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F4 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "LTIP"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F5 · balance_after: Includes 19.1578, 21.1856, and 19.4356 units of phantom stock acquired on July 10, 2025, October 10, 2025, and January 12, 2026 under the LTIP's dividend reinvestment feature.

SEC source: 0001127602-25-012106 · form4.xml · derivative · entry 11

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,478.5125

Underlying: Common Stock · 12 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: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F2 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F2 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F3 · balance_after: Includes 23.883 units of phantom stock acquired on April 10, 2025 under the Plan's dividend reinvestment feature.

SEC source: 0001127602-25-012106 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 103,827.699

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 April 14, 2025, the reporting person's deferred stock units were settled for 12 shares of Community Financial System, Inc. common stock, and .7835 shares were settled in cash at the price of $51.47 per share.

SEC source: 0001127602-25-010083 · form4.xml · derivative · entry 8

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,467.413

Underlying: Common Stock · 1,430 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.

F5 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F5 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F5 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

SEC source: 0001127602-25-010083 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 103,815.699

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 · shares: On March 19, 2025, the reporting person's phantom stock units were settled for 1,430 shares of Community Financial System, Inc. common stock, and .3732 shares were settled in cash at the price of $58.10 per share.

F2 · balance_after: Includes 616.63 shares acquired on January 10, 2025 pursuant to the Community Financial System, Inc. Dividend Reinvestment Plan.

SEC source: 0001127602-25-010083 · form4.xml · derivative · entry 7

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,897.7862

Underlying: Common Stock · 1,225 shares

Expires not disclosed

F5 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F5 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F5 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

SEC source: 0001127602-25-001422 · form4.xml · derivative · entry 7

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,672.7862

Underlying: Common Stock · 712 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.

F5 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F5 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F5 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Financial System, Inc. 2022 Long-Term Incentive Plan, as amended (the "Plan"). Each phantom stock unit which represents a deferred stock unit is the economic equivalent of one share of Community Financial System, Inc. common stock and will be settled in common stock at a predetermined date.

F6 · balance_after: Includes 103.1993 units of phantom stock acquired as dividend equivalents under the Plan.

SEC source: 0001127602-25-001422 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 101,769.069

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 15, 2025, the reporting person's deferred stock units were settled for 712 shares of Community Financial System, Inc. common stock, and .0872 shares were settled in cash at the price of $61.60 per share.

F2 · balance_after: Includes 2,129.519 shares acquired pursuant to the Community Financial System, Inc. Dividend Reinvestment Plan.

SEC source: 0001127602-24-026696 · form4.xml · derivative · entry 6

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 1,969 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.

SEC source: 0001127602-24-026696 · form4.xml · derivative · entry 5

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,123 shares

Expires 2026-03-16

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: 0001127602-24-026696 · form4.xml · nonDerivative · entry 4

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 98,927.55

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $70.50 to $70.945, inclusive. The reporting person undertakes to provide Community Financial System, Inc., any security holder of Community Financial 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: 0001127602-24-026696 · form4.xml · nonDerivative · entry 3

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 100,827.55

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $69.15 to $70.03, inclusive. The reporting person undertakes to provide Community Financial System, Inc., any security holder of Community Financial 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: 0001127602-24-026696 · form4.xml · nonDerivative · entry 2

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 103,019.55

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: 0001127602-24-026696 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 101,050.55

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: 0001127602-24-010840 · form4.xml · derivative · entry 7

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,281.6741

Underlying: Common Stock · 1,395 shares

Expires not disclosed

F5 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Bank System, Inc. 2022 Long-Term Incentive Plan, as amended (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.

F5 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2022 Long-Term Incentive Plan, as amended (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.

F5 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2022 Long-Term Incentive Plan, as amended (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.

F6 · balance_after: Includes 70.518 units of phantom stock acquired as dividend equivalents under the Plan.

SEC source: 0001127602-24-006519 · form4.xml · derivative · entry 12

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 3,631 shares

Expires 2024-03-19

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: 0001127602-24-006519 · form4.xml · nonDerivative · entry 2

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 96,363.602

SEC source: 0001127602-24-006519 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 99,994.602

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: 0001127602-23-026226 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 96,363.602

SEC source: 0001127602-23-010133 · form4.xml · derivative · entry 13

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,816.1561

Underlying: Common Stock · 1,154 shares

Expires not disclosed

F2 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Bank System, Inc. 2022 Long-Term Incentive Plan, as amended (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.

F2 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2022 Long-Term Incentive Plan, as amended (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.

F2 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2022 Long-Term Incentive Plan, as amended (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.

F3 · balance_after: Includes 29.4974 units of phantom stock acquired as dividend equivalents under the Plan.

SEC source: 0001127602-23-010133 · form4.xml · derivative · entry 12

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 468 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: 0001127602-23-010133 · form4.xml · nonDerivative · entry 2

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 85,153.062

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $52.84 to $52.905, 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: 0001127602-23-010133 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 85,621.062

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.

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: 0001127602-22-027798 · 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: 0001127602-22-009751 · form4.xml · derivative · entry 11

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,223.3113

Underlying: Common Stock · 644 shares

Expires not disclosed

F6 · 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.

F6 · 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.

F6 · 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.

F7 · balance_after: Includes 3.1779 units of phantom stock acquired as dividend equivalents under the Plan.

SEC source: 0001127602-21-031324 · form4.xml · derivative · entry 11

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 576.1334

Underlying: Common Stock · 899.2745 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. 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. 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. 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.

F2 · balance_after: Includes 21.7739 units of phantom stock acquired as dividend equivalents under the 2014 Long-Term Incentive Compensation Program.

SEC source: 0001127602-21-031324 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 81,126.1255

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: 0001127602-21-011257 · form4.xml · derivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,453.634

Underlying: Common Stock · 569 shares

Expires not disclosed

F1 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive 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. 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. 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.

F2 · balance_after: Includes 32.5379 units of phantom stock acquired as dividend equivalents under the 2014 Long-Term Incentive Compensation Program.

SEC source: 0001127602-21-008838 · form4.xml · derivative · entry 12

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 4,566 shares

Expires 2022-03-21

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: 0001127602-21-008838 · form4.xml · nonDerivative · entry 2

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 80,226.851

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $71.69 to $72.61, 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: 0001127602-21-008838 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 84,792.851

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 1,594.3124 shares acquired pursuant to the Community Bank System, Inc. Dividend Reinvestment Plan.

SEC source: 0001127602-20-031727 · form4.xml · derivative · entry 11

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 852.0961

Underlying: Common Stock · 622.0556 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. 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. 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. 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: 0001127602-20-031727 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 78,632.5386

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: 0001127602-20-027870 · form4.xml · derivative · entry 12

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 2,640 shares

Expires 2021-01-19

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: 0001127602-20-027870 · form4.xml · nonDerivative · entry 2

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 78,010.483

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $57.76 to $57.82, 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: 0001127602-20-027870 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 80,650.483

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: 0001127602-20-027676 · form4.xml · derivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,474.1517

Underlying: Common Stock · 172 shares

Expires not disclosed

F1 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive 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. 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. 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: 0001127602-20-025983 · form4.xml · derivative · entry 12

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,640

Underlying: Common Stock · 1,210 shares

Expires 2021-01-19

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: 0001127602-20-025983 · form4.xml · nonDerivative · entry 2

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 78,010.483

SEC source: 0001127602-20-025983 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 79,220.483

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: 0001127602-20-011436 · form4.xml · derivative · entry 11

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,302.1517

Underlying: Common Stock · 667 shares

Expires not disclosed

F6 · derivative.exercise_price: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive 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.

F6 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive 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.

F6 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive 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: 0001127602-20-001904 · form4.xml · derivative · entry 13

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 4,892.1843 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.

F5 · 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 · price: On January 15, 2020, the reporting person's phantom stock units were settled for an equal number of shares of Community Bank System, Inc. common stock.

F5 · 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.

F5 · 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.

F6 · derivative.underlying_shares: Includes 117.3117 units of phantom stock acquired under the Deferred Compensation Plan's dividend reinvestment feature.

SEC source: 0001127602-20-001904 · form4.xml · derivative · entry 12

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 635.1517

Underlying: Common Stock · 1,550.418 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 reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive 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 · price: On January 15, 2020, the reporting person's deferred stock units were settled for an equal number of shares of Community Bank System, Inc. common stock.

F3 · derivative.exercise_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive 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.

F3 · derivative.expiration_date: The reporting person has received deferred stock units under the Community Bank System, Inc. 2014 Long-Term Incentive 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.

F4 · balance_after: Includes 49.5575 units of phantom stock acquired as dividend equivalents under the 2014 Long-Term Incentive Compensation Program.

SEC source: 0001127602-20-001904 · form4.xml · nonDerivative · entry 2

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 76,590.4873

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 · price: On January 15, 2020, the reporting person's phantom stock units were settled for an equal number of shares of Community Bank System, Inc. common stock.

SEC source: 0001127602-20-001904 · form4.xml · nonDerivative · entry 1

Bolus Mark J. · CIK 0001486056 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 71,698.303

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 15, 2020, the reporting person's deferred stock units were settled for an equal number of shares of Community Bank System, Inc. common stock.