CBU

SEC source: 0001127602-25-012167 · form4.xml · nonDerivative · entry 1

STEELE SALLY A · CIK 0001264816 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 39,964

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 15, 2025, the reporting person's phantom stock units were settled for 1,181 shares of Community Financial System, Inc. common stock, and .4755 shares were settled in cash at the price of $52.25 per share.

SEC source: 0001127602-25-012170 · form4.xml · derivative · entry 2

Knauss Jeffery J · CIK 0001900543 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,225

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 12.7836 units of phantom stock acquired on April 10, 2025 under the Plan's dividend reinvestment feature.

SEC source: 0001127602-25-012170 · form4.xml · nonDerivative · entry 1

Knauss Jeffery J · CIK 0001900543 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,566.4908

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 phantom stock units were settled for 12 shares of Community Financial System, Inc. common stock, and .7836 shares were settled in cash at the price of $51.47 per share.

SEC source: 0001127602-25-012116 · form4.xml · derivative · entry 3

STICKELS ERIC · CIK 0001201821 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,164.9796

Underlying: Common Stock · 3 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 30.0748 units of phantom stock acquired on April 10, 2025 under the Plan's dividend reinvestment feature.

SEC source: 0001127602-25-012116 · form4.xml · nonDerivative · entry 1

STICKELS ERIC · CIK 0001201821 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 35,342

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 phantom stock units were settled for 3 shares of Community Financial System, Inc. common stock, and .8351 shares were settled in cash at the price of $51.47 per share."

SEC source: 0001127602-25-012098 · form4.xml · derivative · entry 2

Parente John · CIK 0001486057 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,225

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_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 12.7836 units of phantom stock acquired on April 10, 2025 under the Plan's dividend reinvestment feature.

SEC source: 0001127602-25-012098 · form4.xml · nonDerivative · entry 1

Parente John · CIK 0001486057 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 69,828.3212

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 phantom stock units were settled for 12 shares of Community Financial System, Inc. common stock, and .7836 shares were settled in cash at the price of $51.74 per share.

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: 0001127602-25-010642 · form4.xml · derivative · entry 1

Fesette Neil E. · CIK 0001485738 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,903.3714

Underlying: Common Stock · 202.6432 shares

Expires not disclosed

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

SEC source: 0001127602-25-010640 · form4.xml · derivative · entry 1

Singh Savneet · CIK 0001738659 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 308.37

Underlying: Common Stock · 308.37 shares

Expires not disclosed

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

SEC source: 0001127602-25-010160 · form4.xml · derivative · entry 2

Sullivan Michele · CIK 0002009605 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,715.0923

Underlying: Common Stock · 344.9465 shares

Expires not disclosed

F3 · derivative.exercise_price: Each unit of phantom stock is the economic equivalent of one share of Community Financial System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Financial System, Inc. common stock at future dates selected by the reporting person.

F3 · derivative.exercise_date: Each unit of phantom stock is the economic equivalent of one share of Community Financial System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Financial System, Inc. common stock at future dates selected by the reporting person.

F3 · derivative.expiration_date: Each unit of phantom stock is the economic equivalent of one share of Community Financial System, Inc. common stock. The units of phantom stock relating to the Deferred Compensation Plan will be settled in Community Financial System, Inc. common stock at future dates selected by the reporting person.

F4 · balance_after: Includes 8.1166 units of phantom stock acquired as dividend equivalents on January 10, 2025 under the Deferred Compensation Plan.

SEC source: 0001127602-25-010090 · form4.xml · derivative · entry 3

Parente John · CIK 0001486057 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,225

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.

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.

SEC source: 0001127602-25-010090 · form4.xml · nonDerivative · entry 1

Parente John · CIK 0001486057 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 69,816.3212

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 .373 shares were settled in cash at the price of $58.10 per share.

SEC source: 0001127602-25-010088 · form4.xml · derivative · entry 3

Knauss Jeffery J · CIK 0001900543 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,225

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.

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.

SEC source: 0001127602-25-010088 · form4.xml · nonDerivative · entry 1

Knauss Jeffery J · CIK 0001900543 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,554.4908

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 .373 shares were settled in cash at the price of $58.10 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: 0001127602-25-010048 · form4.xml · derivative · entry 3

Abdo Michael N · CIK 0001933852 · EVP and General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,898

Underlying: Common Stock · 4,898 shares

Expires 2035-03-18

F2 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-010048 · form4.xml · nonDerivative · entry 1

Abdo Michael N · CIK 0001933852 · EVP and General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,730

SEC source: 0001127602-25-010047 · form4.xml · derivative · entry 4

Durkee Deresa Fischer · CIK 0001608689 · SVP, Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,262

Underlying: Common Stock · 3,262 shares

Expires 2035-03-18

F2 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-010047 · form4.xml · nonDerivative · entry 1

Durkee Deresa Fischer · CIK 0001608689 · SVP, Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,537.604

SEC source: 0001127602-25-010044 · form4a.xml · derivative · entry 3

LEVY JEFFREY M · CIK 0001384972 · SVP & Chief Banking Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,217

Underlying: Common Stock · 5,217 shares

Expires 2035-03-18

F3 · shares: This amendment is filed to correct the number of stock options acquired. The correct number is 5,217 shares.

F4 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-010044 · form4a.xml · nonDerivative · entry 1

LEVY JEFFREY M · CIK 0001384972 · SVP & Chief Banking Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,096.6389

F1 · shares: This amendment is filed to correct the number of shares of restricted stock acquired. The correct number is 1,413 shares.

SEC source: 0001127602-25-010036 · form4a.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,647

Underlying: Common Stock · 5,647 shares

Expires 2035-03-18

F3 · shares: This amendment is filed to correct the number of stock options acquired. The correct number is 5,647 shares.

F4 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-010036 · form4a.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,879.9958

F1 · shares: This amendment is filed to correct the number of shares of restricted stock acquired. The correct number is 1,529 shares.

SEC source: 0001127602-25-010039 · form4a.xml · derivative · entry 3

Gillan-Myer Maureen A · CIK 0001670754 · EVP, Chief Admin & HR Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,553

Underlying: Common Stock · 4,553 shares

Expires 2035-03-18

F3 · shares: This amendment is filed to correct the number of stock options acquired. The correct number is 4,553 shares.

F4 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-010039 · form4a.xml · nonDerivative · entry 1

Gillan-Myer Maureen A · CIK 0001670754 · EVP, Chief Admin & HR Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,550

F1 · shares: This amendment is filed to correct the number of shares of restricted stock acquired. The correct number is 1,233 shares.

SEC source: 0001127602-25-010024 · form4a.xml · derivative · entry 3

Karaivanov Dimitar · CIK 0001866135 · Director · President & CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,725

Underlying: Common Stock · 16,725 shares

Expires 2035-03-18

F3 · shares: This amendment is filed to correct the number of stock options acquired. The correct number is 16,725 shares.

F4 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-010024 · form4a.xml · nonDerivative · entry 1

Karaivanov Dimitar · CIK 0001866135 · Director · President & CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,759

F1 · shares: This amendment is filed to correct the number of shares of restricted stock acquired. The correct number is 4,529 shares.

SEC source: 0001127602-25-010011 · form4.xml · derivative · entry 3

Gillan-Myer Maureen A · CIK 0001670754 · EVP, Chief Admin & HR Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,233

Underlying: Common Stock · 1,233 shares

Expires 2035-03-18

F2 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-010011 · form4.xml · nonDerivative · entry 1

Gillan-Myer Maureen A · CIK 0001670754 · EVP, Chief Admin & HR Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,870

SEC source: 0001127602-25-009998 · form4.xml · derivative · entry 3

LEVY JEFFREY M · CIK 0001384972 · SVP & Chief Banking Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,413

Underlying: Common Stock · 1,413 shares

Expires 2035-03-18

F2 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-009998 · form4.xml · nonDerivative · entry 1

LEVY JEFFREY M · CIK 0001384972 · SVP & Chief Banking Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,900.6389

SEC source: 0001127602-25-009984 · form4.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,529

Underlying: Common Stock · 1,529 shares

Expires 2035-03-18

F2 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-009984 · form4.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,997.9958

SEC source: 0001127602-25-009960 · form4.xml · derivative · entry 3

Karaivanov Dimitar · CIK 0001866135 · Director · President & CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,529

Underlying: Common Stock · 4,529 shares

Expires 2035-03-18

F2 · derivative.exercise_date: The option vests ratably on March 18, 2026, 2027, 2028, 2029, and 2030.

SEC source: 0001127602-25-009960 · form4.xml · nonDerivative · entry 1

Karaivanov Dimitar · CIK 0001866135 · Director · President & CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 35,955

SEC source: 0001127602-25-009938 · form4.xml · derivative · entry 1

Singh Savneet · CIK 0001738659 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,225

Underlying: Common Stock · 1,225 shares

Expires not disclosed

F1 · 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.

F1 · 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.

F1 · 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: 0001127602-25-009923 · form4.xml · derivative · entry 1

STICKELS ERIC · CIK 0001201821 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,138.7399

Underlying: Common Stock · 1,225 shares

Expires not disclosed

F1 · 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.

F1 · 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.

F1 · 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: 0001127602-25-010166 · form4.xml · derivative · entry 2

Whipple John F. · CIK 0001485739 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,249.4117

Underlying: Common Stock · 1,225 shares

Expires not disclosed

F3 · 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.

F3 · 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.

F4 · balance_after: Includes 25.8915, 36.6659, 31.555, and 31.3024 units of phantom stock acquired as dividend equivalents on April 10, 2024, July 10, 2024, October 10, 2024, and January 10, 2025, respectively, under the Plan.

SEC source: 0001127602-25-010160 · form4.xml · derivative · entry 1

Sullivan Michele · CIK 0002009605 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,655.373

Underlying: Common Stock · 1,225 shares

Expires not disclosed

F1 · 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.

F1 · 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.

F1 · 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.

F2 · balance_after: Includes 13.032, 11.2154, and 11.1256 units of phantom stock acquired as dividend equivalents on July 10, 2024, October 10, 2024, and January 10, 2025, respectively, under the Plan.

SEC source: 0001127602-25-010132 · form4.xml · derivative · entry 1

STEELE SALLY A · CIK 0001264816 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,406.7735

Underlying: Common Stock · 1,225 shares

Expires not disclosed

F1 · 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.

F1 · 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.

F1 · 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.

F2 · balance_after: Includes 13.032, 11.2154, and 9.1082 units of phantom stock acquired as dividend equivalents on July 10, 2024, October 10, 2024, and January 10, 2025, respectively, under the Plan.

SEC source: 0001127602-25-010114 · form4.xml · derivative · entry 1

SKERRITT SUSAN E · CIK 0001748654 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,249.4118

Underlying: Common Stock · 1,225 shares

Expires not disclosed

F1 · 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.

F1 · 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.

F2 · balance_after: Includes 25.8915, 36.666, 31.5553, and 31.3025 units of phantom stock acquired as dividend equivalents on April 10, 2024, July 10, 2024, October 10, 2024, and January 10, 2025, respectively, under the Plan.

SEC source: 0001127602-25-010091 · form4.xml · derivative · entry 5

Pecor Raymond C III · CIK 0001475265 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,949.7799

Underlying: Common Stock · 1,225 shares

Expires not disclosed

F8 · 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.

F8 · 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.

F8 · 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.

F9 · balance_after: Includes 43.1123, 52.3854, 45.0833, and 44.7223 units of phantom stock acquired as dividend equivalents on April 10, 2024, July 10, 2024, October 10, 2024, and January 10, 2025, respectively, under the Plan.

SEC source: 0001127602-25-010090 · form4.xml · derivative · entry 2

Parente John · CIK 0001486057 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,655.373

Underlying: Common Stock · 1,225 shares

Expires not disclosed

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 13.032, 11.2154, and 11.1256 units of phantom stock acquired as dividend equivalents on July 10, 2024, October 10, 2024, and January 10, 2025, respectively, under the Plan.

SEC source: 0001127602-25-010089 · form4.xml · derivative · entry 1

MacPherson Kerrie D. · CIK 0001794595 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,215.2763

Underlying: Common Stock · 1,225 shares

Expires not disclosed

F1 · 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.

F1 · 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.

F1 · 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.

F2 · balance_after: Includes 35.5319, 45.4659, 39.1285, and 38.8151 units of phantom stock acquired as dividend equivalents on April 10, 2024, July 10, 2024, October 10, 2024, and January 10, 2025, respectively, under the Plan.

SEC source: 0001127602-25-010088 · form4.xml · derivative · entry 2

Knauss Jeffery J · CIK 0001900543 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,655.373

Underlying: Common Stock · 1,225 shares

Expires not disclosed

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 13.032, 11.2154, and 11.1256 units of phantom stock acquired as dividend equivalents on July 10, 2024, October 10, 2024, and January 10, 2025, respectively, under the Plan.

SEC source: 0001127602-25-010085 · form4.xml · derivative · entry 3

Fesette Neil E. · CIK 0001485738 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,841.1314

Underlying: Common Stock · 1,225 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 "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.

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 "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.

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 "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 · balance_after: Includes 35.5319, 45.4658, 39.1283, and 31.3024 units of phantom stock acquired as dividend equivalents on April 10, 2024, July 10, 2024, October 10, 2024, and January 10, 2025, respectively, under the 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.