Community Bank System, Inc. Contracts & Agreements

Community Bank System, Inc. Executive Severance Plan, dated July 18, 2023 (Filed With SEC on July 21, 2023)

Employment Agreement, dated July 5, 2023, by and among Community Bank System, Inc., Community Bank, N.A., and Dimitar Karaivanov (Filed With SEC on July 5, 2023)

Description of Community Bank System, Inc.s securities registered pursuant to Section 12 of the Securities Exchange Act (Filed With SEC on March 1, 2023)

Amendment to Employment Agreement, effective August 24, 2022, by and among Community Bank System, Inc., Community Bank, N.A., and Dimitar Karaivanov (Filed With SEC on August 26, 2022)

Retirement Agreement, dated August 24, 2022, by and among Community Bank System, Inc., Community Bank, N.A. and Joseph F. Serbun (Filed With SEC on August 26, 2022)

Employment Agreement, dated March 22, 2021, by and among Community Bank System, Inc., Community Bank, N.A. and Dimitar Karaivanov (Filed With SEC on May 10, 2022)

Community Bank System, Inc. 2022 Long-Term Incentive Plan, as amended (Filed With SEC on May 6, 2022)

Amendment to Employment Agreement, dated April 28, 2022, by and among Community Bank System, Inc., Community Bank, N.A. and George J. Getman (Filed With SEC on April 29, 2022)

Description of Community Bank System, Inc.s securities registered pursuant to Section 12 of the Securities Exchange Act (Filed With SEC on March 1, 2022)

Employment Agreement, dated January 5, 2022, by and among Community Bank System, Inc., Community Bank, N.A., and Joseph F. Serbun (Filed With SEC on January 6, 2022)

Agreement and Plan of Merger, dated October 3, 2021, by and among Community Bank, N.A., Eagle Merger Sub Inc., and Elmira Savings Bank (Filed With SEC on October 7, 2021)

Employment Agreement, dated December 29, 2020, by and among Community Bank System, Inc., Community Bank, N.A. and Joseph J. Lemchak (Filed With SEC on May 10, 2021)

Description of Community Bank System, Inc.s securities registered pursuant to Section 12 of the Securities Exchange Act (Filed With SEC on March 1, 2021)

Employment Agreement, dated January 4, 2021, by and among Community Bank System, Inc., Community Bank, N.A. and Mark E. Tryniski (Filed With SEC on January 6, 2021)

Employment Agreement, dated January 4, 2021, by and among Community Bank System, Inc., Community Bank, N.A. and Joseph E. Sutaris (Filed With SEC on January 6, 2021)

Retirement and Release Agreement, dated March 13, 2020, by and among Community Bank System, Inc., Community Bank, N.A. and Scott A. Kingsley (Filed With SEC on March 19, 2020)

Amendment to Employment Agreement, dated March 13, 2020, by and among Community Bank System, Inc., Community Bank, N.A. and Joseph F. Serbun (Filed With SEC on March 19, 2020)

Description of Community Bank System, Inc.s securities registered pursuant to Section 12 of the Securities Exchange Act (Filed With SEC on March 2, 2020)

Employment Agreement, dated December 31, 2019, by and among Community Bank System, Inc., Community Bank, N.A. and Scott A. Kingsley (Filed With SEC on January 7, 2020)

Employment Agreement, dated December 31, 2019, by and among Community Bank System, Inc., Community Bank, N.A. and George J. Getman (Filed With SEC on January 7, 2020)

Agreement and Plan of Merger, dated as of October 18, 2019, by and between Community Bank System, Inc. and Steuben Trust Corporation (Filed With SEC on October 24, 2019)

Agreement and Plan of Merger, dated as of January 21, 2019, by and among Community Bank System, Inc., VB Merger Sub Inc., and Kinderhook Bank Corp (Filed With SEC on January 25, 2019)

Employment Agreement, dated January 4, 2019, by and among Community Bank System, Inc., Community Bank, N.A. and Joseph F. Serbun (Filed With SEC on January 8, 2019)

Amendment to Employment Agreement, effective June 1, 2018, by and among Community Bank System, Inc., Community Bank, N.A. and Scott Kingsley (Filed With SEC on May 21, 2018)

Employment Agreement, effective June 1, 2018, by and among Community Bank System, Inc., Community Bank, N.A. and Joseph E. Sutaris (Filed With SEC on May 21, 2018)

Amendment to Employment Agreement, effective June 1, 2018, by and among Community Bank System, Inc., Community Bank, N.A. and Joseph F. Serbun (Filed With SEC on May 21, 2018)

Community Bank System, Inc. Restoration Plan, effective June 1, 2018 (Filed With SEC on May 21, 2018)

Amendment to Employment Agreement, dated March 19, 2018, by and among Community Bank System, Inc., Community Bank, N.A. and Brian D. Donahue (Filed With SEC on March 20, 2018)

Employment Agreement, dated January 5, 2018, by and among Community Bank System, Inc., Community Bank, N.A. and Mark E. Tryniski (Filed With SEC on January 5, 2018)

Amendment to Supplemental Retirement Plan Agreement, dated January 5, 2018, by and among Community Bank System, Inc., Community Bank, N.A. and Mark E. Tryniski (Filed With SEC on January 5, 2018)

FORM OF SECOND REPLACEMENT ORGANIZER WARRANT CERTIFICATE (Filed With SEC on May 18, 2017)

FIRST SUPPLEMENTAL INDENTURE (Filed With SEC on May 18, 2017)

COMMUNITY BANK SYSTEM, INC. 2014 LONG-TERM INCENTIVE PLAN, AS AMENDED Table of Contents (Filed With SEC on May 2, 2017)

EMPLOYMENT AGREEMENT (Filed With SEC on January 6, 2017)

AGREEMENT AND PLAN OF MERGER BY AND AMONG COMMUNITY BANK SYSTEM, INC. COHIBA MERGER SUB, LLC NORTHEAST RETIREMENT SERVICES, INC. and SHAREHOLDER REPRESENTATIVE SERVICES LLC as... (Filed With SEC on December 8, 2016)

AGREEMENT AND PLAN OF MERGER BY AND BETWEEN COMMUNITY BANK SYSTEM, INC. AND MERCHANTS BANCSHARES, INC. Dated as of October 22, 2016 (Filed With SEC on October 27, 2016)

EMPLOYMENT AGREEMENT (Filed With SEC on March 16, 2016)

EMPLOYMENT AGREEMENT (Filed With SEC on January 2, 2015)

EMPLOYMENT AGREEMENT (Filed With SEC on January 3, 2014)

EMPLOYMENT AGREEMENT (Filed With SEC on October 23, 2013)

SUPPLEMENTAL RETIREMENT PLAN AGREEMENT (Filed With SEC on October 23, 2013)

PURCHASE AND ASSUMPTION AGREEMENT dated as of July 23, 2013 between BANK OF AMERICA, NATIONAL ASSOCIATION and COMMUNITY BANK, NATIONAL ASSOCIATION (Filed With SEC on July 26, 2013)

EMPLOYMENT AGREEMENT (Filed With SEC on May 10, 2013)

1,852,000 Shares1COMMUNITY BANK SYSTEM, INC.Common Stock, $1.00 Par ValueUNDERWRITING AGREEMENT (Filed With SEC on January 27, 2012)

ASSIGNMENT, PURCHASE AND ASSUMPTION AGREEMENT by and between FIRST NIAGARA BANK, NATIONAL ASSOCIATION and COMMUNITY BANK, NATIONAL ASSOCIATION JANUARY 19, 2012 TABLE OF CONTENTS (Filed With SEC on January 20, 2012)

PURCHASE AND ASSUMPTION AGREEMENT (Filed With SEC on January 20, 2012)

EMPLOYMENT AGREEMENT (Filed With SEC on December 30, 2011)

COMMUNITY BANK SYSTEM, INC. 2004 LONG-TERM INCENTIVE COMPENSATION PROGRAM, AS TO BE AMENDED (Filed With SEC on May 12, 2011)

EMPLOYMENT AGREEMENT (Filed With SEC on January 6, 2011)

AGREEMENT (Filed With SEC on January 6, 2011)

AGREEMENT AND PLAN OF MERGER dated as of October 22, 2010 among COMMUNITY BANK SYSTEM, INC., and THE WILBER CORPORATION TABLE OF CONTENTS (Filed With SEC on October 25, 2010)

EMPLOYMENTAGREEMENT (Filed With SEC on February 3, 2010)

SUPPLEMENTAL RETIREMENT PLANAGREEMENT (Filed With SEC on October 1, 2009)

SUPPLEMENTAL RETIREMENT PLAN AGREEMENT (Filed With SEC on April 14, 2009)

EMPLOYMENTAGREEMENT (Filed With SEC on March 19, 2009)

SUPPLEMENTAL RETIREMENT PLANAGREEMENT (Filed With SEC on March 19, 2009)

EMPLOYMENTAGREEMENT (Filed With SEC on March 13, 2009)

PURCHASE AND ASSUMPTION AGREEMENT (Filed With SEC on June 26, 2008)

Employment Agreement dated January 1, 2008, by and among Community Bank System, Inc., Community Bank, N.A. and George J. Getman (Filed With SEC on May 8, 2008)

EMPLOYMENT AGREEMENT (Filed With SEC on April 9, 2008)

Supplemental Retirement Plan Agreement, by and between Community Bank System Inc. and Mark E. Tryniski (Filed With SEC on May 8, 2007)

AMENDED AND RESTATED DECLARATION (Filed With SEC on December 12, 2006)

GUARANTEE AGREEMENT (Filed With SEC on December 12, 2006)