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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">As filed with the Securities and Exchange Commission
    on May 30, 2025</P>
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    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; font-size: 10pt; text-align: right"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Registration No. 333-&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>UNITED STATES</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SECURITIES AND EXCHANGE COMMISSION</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Washington, D.C. 20549</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"></P>

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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>FORM S-8</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>REGISTRATION STATEMENT</B></P>
    <P STYLE="text-align: center; font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><B>&#9;UNDER THE SECURITIES ACT OF 1933&#9;</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"></P>

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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><IMG SRC="image_001.jpg" ALT="" STYLE="height: 107px; width: 304px"></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Exact name of registrant as specified in its charter)</P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Delaware</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(State or other jurisdiction</P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">of incorporation or organization)</P></TD>
    <TD STYLE="width: 50%; padding-right: 5.4pt; padding-left: 5.4pt">
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>16-1213679</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(I.R.S. Employer</P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">Identification No.)</P></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>5790 Widewaters Parkway</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Dewitt, New York 13214</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Address of Principal Executive Offices) (Zip Code)</P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"></P>

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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Community Financial System, Inc. 401(k) Employee
    Stock Ownership Plan</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Full title of the plan)</P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Michael N. Abdo, Esq.</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Executive Vice President and General Counsel</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>5790 Widewaters Parkway</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>DeWitt, New York 13214</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Name and address of agent for service)</P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>(315) 445-2282</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Telephone number, including area code, of agent
for service)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P></TD></TR>
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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">Indicate by check mark whether the registrant is a large accelerated
filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definitions of
 &ldquo;large accelerated filer,&rdquo; &ldquo;accelerated filer,&rdquo; &ldquo;smaller reporting company,&rdquo; and &ldquo;emerging growth
company&rdquo; in Rule 12b-2 of the Exchange Act.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"></P>

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<TD STYLE="padding-bottom: 2pt; width: 20%">Large
    accelerated filer
<TD STYLE="padding-bottom: 2pt; width: 30%"><FONT STYLE="font-family: Wingdings">&#120;</FONT></TD><TD STYLE="padding-bottom: 2pt; width: 20%; text-align: left">Accelerated
filer</TD><TD STYLE="padding-bottom: 2pt; text-align: justify; width: 30%"><FONT STYLE="font-family: Wingdings">&#168;</FONT>&nbsp;</TD>
</TR><TR STYLE="vertical-align: top; text-align: justify">
<TD STYLE="padding-bottom: 2pt">Non-accelerated
    filer</TD>
<TD STYLE="padding-bottom: 2pt"><FONT STYLE="font-family: Wingdings">&#168;</FONT>&nbsp;</TD><TD STYLE="padding-bottom: 2pt; text-align: left">Smaller reporting company</TD><TD STYLE="padding-bottom: 2pt; text-align: justify"><FONT STYLE="font-family: Wingdings">&#168;</FONT></TD></TR>
     <TR STYLE="vertical-align: top; text-align: justify">
<TD>&nbsp;</TD>
<TD>&nbsp;</TD><TD STYLE="text-align: left">Emerging growth company</TD><TD STYLE="text-align: justify"><FONT STYLE="font-family: Wingdings">&#168;</FONT></TD></TR>
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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">If
an emerging growth company, indicated by check mark if the registration has elected not to use the extended transition period for complying
with any new or revised financial accounting standards provided pursuant to Section&nbsp;7(a)(2)(B)&nbsp;of the Securities Act.&#8239;</FONT></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; text-align: right; margin-top: 0pt; margin-bottom: 0pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&#8239;<FONT STYLE="font-family: Wingdings">&#168;</FONT></FONT></P>


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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>INTRODUCTION</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>&nbsp;</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">This Registration Statement
on Form S-8 is filed by Community Financial System, Inc. (the &ldquo;Registrant&rdquo;) to register an additional 1,500,000 shares of
the Registrant&rsquo;s common stock, par value $1.00 per share (&ldquo;Common Stock&rdquo;), which may be issued under the Community Financial
System, Inc. 401(k) Employee Stock Ownership Plan (the &ldquo;Plan&rdquo;). We intend to issue the Common Stock with open market purchases.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>PART I</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>INFORMATION REQUIRED IN THE SECTION 10(a) PROSPECTUS</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">The documents containing the
information required in Part I of Form S-8 will be delivered to participants in the Plan in accordance with Form S&minus;8 and Rule 428(b)
under the Securities Act of 1933, as amended (the &ldquo;Securities Act&rdquo;). Such documents are not required to be, and are not, filed
with the Securities and Exchange Commission (&ldquo;Commission&rdquo;) either as part of this Registration Statement or as prospectuses
or prospectus supplements pursuant to Rule 424 under the Securities Act. These documents and the documents incorporated herein by reference
pursuant to Item 3 of Part II of this Registration Statement, taken together, constitute a prospectus that meets the requirements of Section
10(a) of the Securities Act.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>PART II</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>INFORMATION REQUIRED IN THE REGISTRATION STATEMENT</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

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<TD STYLE="width: 0"></TD><TD STYLE="width: 1in"><B>Item 3.</B></TD><TD STYLE="text-align: justify"><B>Incorporation of Documents by Reference</B>.</TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">The following documents, which
have been filed by the Registrant (Commission File No. 001-13695) with the Commission pursuant to the Securities Exchange Act of 1934
(the &ldquo;Exchange Act&rdquo;), are incorporated in this registration statement by reference:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">(a) The Registrant&rsquo;s
Annual Report on Form 10&minus;K for the fiscal year ended December 31, 2024, filed with the Commission on<A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/723188/000141057825000247/cbu-20241231x10k.htm" STYLE="-sec-extract: exhibit"> February 28, 2025</A>.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">(b) The Registrant&rsquo;s
Quarterly Report on Form 10&minus;Q for the fiscal quarter ended March 31, 2025, filed with the Commission on <A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/723188/000141057825001170/cbu-20250331x10q.htm" STYLE="-sec-extract: exhibit">May 9, 2025</A>.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">(c) The Registrant&rsquo;s
Current Reports on Form 8&minus;K filed on <A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/723188/000110465925014186/tm256547d1_8k.htm" STYLE="-sec-extract: exhibit">February 14, 2025</A>, <A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/723188/000110465925022380/tm258776d1_8k.htm" STYLE="-sec-extract: exhibit">March 11, 2025</A>, and <A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/723188/000110465925052458/tm2516011d1_8k.htm" STYLE="-sec-extract: exhibit">May 23, 2025</A>.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">(d) The portions of the Registrant&rsquo;s
Definitive Proxy Statement on Schedule 14A for the Registrant&rsquo;s 2025 Annual Meeting of Stockholders, filed with the Commission on
<A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/723188/000114036125010845/ny20037448x1_def14a.htm" STYLE="-sec-extract: exhibit">March 28, 2025</A>, that are incorporated by reference into Part III of the Registrant&rsquo;s Annual Report on Form 10-K for the fiscal year
ended December 31, 2024.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">(e) The description of the
Company&rsquo;s common stock contained in the Registration Statement on Form 8-A (File No. 001-13695) filed on <A HREF="https://www.sec.gov/Archives/edgar/data/723188/0000950110-97-001618.txt" STYLE="-sec-extract: exhibit">December 9, 1997</A>, including
any amendments or reports filed for the purpose of updating such description.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">All documents subsequently
filed by the Registrant pursuant to Sections 13(a), 13(c), 14 and 15(d) of the Exchange Act (other than current reports on Form 8&minus;K
furnished pursuant to Item 2.02 or Item 7.01 of Form 8&minus;K, including any exhibits included with such information, unless otherwise
indicated therein), and prior to the filing of a post&minus;effective amendment which indicates that all securities offered hereby have
been sold or which deregisters all securities then remaining unsold, shall be deemed to be incorporated by reference herein and to be
a part hereof from the date of filing of such documents.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">Any statement contained herein
or in a document incorporated or deemed to be incorporated by reference herein shall be deemed to be modified or superseded for purposes
of this registration statement to the extent that a statement contained herein or in any other subsequently filed document which also
is or is deemed to be incorporated by reference herein, or any document forming any part of the Section 10(a) prospectus to be delivered
to participants in connection herewith, modifies or supersedes such statement. Any statement so modified or superseded shall not be deemed,
except as so modified or superseded, to constitute part of this Registration Statement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in"></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

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<TD STYLE="width: 0"></TD><TD STYLE="width: 1in"><B>Item 4.</B></TD><TD STYLE="text-align: justify"><B>Description of Securities.</B></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">Not applicable.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

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<TD STYLE="width: 0"></TD><TD STYLE="width: 1in"><B>Item 5.</B></TD><TD STYLE="text-align: justify"><B>Interests of Named Experts and Counsel.</B></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">Not applicable.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

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<TD STYLE="width: 0"></TD><TD STYLE="width: 1in"><B>Item 6.</B></TD><TD STYLE="text-align: justify"><B>Indemnification of Directors and Officers.</B></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">The Registrant is a Delaware
corporation. Section 145 of the Delaware General Corporation Law (the &ldquo;DGCL&rdquo;) provides that a corporation may indemnify any
person who was or is a party or is threatened to be made a party to any threatened, pending or completed action, suit or proceeding, whether
civil, criminal, administrative or investigative (other than an action by or in the right of the corporation) by reason of the fact that
the person is or was a director, officer, employee, or agent of the corporation, or is or was serving at the request of the corporation
as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise, against expenses
(including attorneys&rsquo; fees), judgments, fines and amounts paid in settlement actually and reasonably incurred by the person in connection
with such action, suit or proceeding, provided that such person acted in good faith and in a manner reasonably believed to be in, or not
opposed to, the best interests of the corporation, and, with respect to any criminal action or proceeding, had no reasonable cause to
believe that his or her conduct was unlawful.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">This power to indemnify applies
to actions or suits brought by or in the right of the corporation to procure a judgment in its favor as well, but only to the extent of
expenses (including attorneys&rsquo; fees but excluding amounts paid in settlement) actually and reasonably incurred by the person in
connection with the defense or settlement of such action or suit if such person acted in good faith and in a manner reasonably believed
to be in, or not opposed to, the best interests of the corporation, except that no indemnification shall be made in respect of any claim,
issue or matter as to which such person shall have been adjudged to be liable to the corporation, unless and only to the extent that the
Delaware Court of Chancery or the court in which such action was brought shall determine upon application that, despite the adjudication
of liability but in view of all the circumstances of the case, such person is fairly and reasonably entitled to indemnity for such expenses
which the court shall deem proper.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">Section 145 of the DGCL further
provides that to the extent a director or officer of a corporation has been successful in the defense of any action, suit or proceeding
referred to in subsections (a) and (b) of Section 145, or in the defense of any claim, issue or matter therein, he or she shall be indemnified
against expenses (including attorneys&rsquo; fees) actually and reasonably incurred by him or her in connection therewith; that indemnification
provided for by Section 145 shall not be deemed exclusive of any other rights to which the indemnified party may be entitled; and that
the corporation shall have power to purchase and maintain insurance on behalf of a director or officer of the corporation against any
liability asserted against him or her or incurred by him or her in any such capacity or arising out of his or her status as such whether
or not the corporation would have the power to indemnify him or her against such liabilities under Section 145.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">Article 9 of the Registrant&rsquo;s
Amended and Restated Certificate of Incorporation provides that the Registrant&rsquo;s directors shall not be liable to the Registrant
or its shareholders for monetary damages as a result of breach of fiduciary duty, except for liability in connection with a breach of
a director&rsquo;s duty of loyalty, for acts or omissions not in good faith or involving intentional misconduct or a knowing violation
of the law, for a transaction from which a director derives an improper personal benefit, or for liability arising under Section 174 of
the DGCL.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">Article 7 of the Registrant&rsquo;s
Bylaws provides that the Registrant shall indemnify any person made, or threatened to be made, a party to an action, suit or proceeding,
whether criminal, civil, administrative or investigative, by reason of the fact that he or she is or was a director or officer of the
registrant against expenses (including attorney&rsquo;s fees), judgments, fines and amounts paid in settlement, to the fullest extent
and in the manner set forth in and permitted by the DGCL, and any other applicable law, as from time to time in effect.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">The Registrant is insured
against liabilities it may incur by reason of its indemnification of officers and directors in accordance with its Bylaws. In addition,
as permitted under Delaware law, the Registrant maintains liability insurance covering directors and officers of the Registrant and its
subsidiaries.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">The foregoing summaries are
necessarily subject to the complete texts of Section 145 of the DGCL, the Registrant&rsquo;s Certificate of Incorporation, as amended,
and the Registrant&rsquo;s Bylaws, as amended, referred to above and are qualified in their entirety by reference thereto.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in"></P>

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    <DIV STYLE="break-before: page; margin-top: 6pt; margin-bottom: 12pt"><P STYLE="margin: 0pt">&nbsp;</P></DIV>
    <!-- Field: /Page -->

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0"></TD><TD STYLE="width: 1in"><B>Item 7.</B></TD><TD STYLE="text-align: justify"><B>Exemption from Registration Claimed.</B></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 63pt; text-align: justify; text-indent: -27pt">Not applicable.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 63pt; text-align: justify; text-indent: -27pt">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0"></TD><TD STYLE="width: 1in"><B>Item 8.</B></TD><TD STYLE="text-align: justify"><B>Exhibits.</B></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 36pt"></TD><TD STYLE="width: 27pt"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000110465924062598/tm2414533d1_ex3-1.htm" STYLE="-sec-extract: exhibit">4.1</A></TD><TD STYLE="text-align: justify; padding-right: 0.5in"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000110465924062598/tm2414533d1_ex3-1.htm" STYLE="-sec-extract: exhibit">Amended and Restated Certificate of Incorporation of Registrant. Incorporated by
reference to Exhibit No. 3.1 to the Current Report on Form 8-K filed with the Commission on May 16, 2024.</A></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 36pt"></TD><TD STYLE="width: 27pt"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000110465924062598/tm2414533d1_ex3-2.htm" STYLE="-sec-extract: exhibit">4.2</A></TD><TD STYLE="text-align: justify; padding-right: 0.5in"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000110465924062598/tm2414533d1_ex3-2.htm" STYLE="-sec-extract: exhibit">Bylaws of Registrant, as amended and restated. Incorporated by reference to Exhibit
3.2 to the Current Report on Form 8-K filed with the Commission on May 16, 2024.</A></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 36pt"></TD><TD STYLE="width: 27pt"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000072318813000044/cbnas82013ex45.htm" STYLE="-sec-extract: exhibit">4.3</A></TD><TD STYLE="text-align: justify; padding-right: 0.5in"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000072318813000044/cbnas82013ex45.htm" STYLE="-sec-extract: exhibit">Community Financial System, Inc. 401(k) Employee Stock Ownership Plan, dated as
of December 20, 2011. Incorporated by reference to Exhibit 4.5 to the Registration Statement on Form S-8 filed on December 20, 2013 (Registration
No. 001-13695).</A></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 36pt"></TD><TD STYLE="width: 27pt"><A HREF="tm2516268d1_ex23-1.htm">23.1</A></TD><TD STYLE="text-align: justify"><A HREF="tm2516268d1_ex23-1.htm">Consent of PricewaterhouseCoopers LLP.</A></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 36pt"></TD><TD STYLE="width: 27pt"><A HREF="#a_001">24.1</A></TD><TD STYLE="text-align: justify"><A HREF="#a_001">Power of Attorney (contained on the Signature Page of this registration statement).</A></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 36pt"></TD><TD STYLE="width: 27pt"><A HREF="tm2516268d1_ex-filingfees.htm">107</A></TD><TD STYLE="text-align: justify"><A HREF="tm2516268d1_ex-filingfees.htm">Filing fee table</A></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0"></TD><TD STYLE="width: 1in"><B>Item 9.</B></TD><TD STYLE="text-align: justify"><B>Undertakings.</B></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">(a)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The
undersigned Registrant hereby undertakes:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">(1)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;To
file, during any period in which offers or sales are being made, a post-effective amendment to this Registration Statement:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 1in"></TD><TD STYLE="width: 0.5in">(i)</TD><TD STYLE="text-align: justify">To include any prospectus required by Section 10(a)(3) of the Securities Act of 1933;</TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 1in"></TD><TD STYLE="width: 0.5in">(ii)</TD><TD STYLE="text-align: justify">To reflect in the prospectus any facts or events arising after the effective date of the Registration
Statement (or the most recent post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change
in the information set forth in the Registration Statement; and</TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 1in"></TD><TD STYLE="width: 0.5in">(iii)</TD><TD STYLE="text-align: justify">To include any material information with respect to the plan of distribution not previously disclosed
in the Registration Statement or any material change to such information in the Registration Statement;</TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"></P>

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    <DIV STYLE="break-before: page; margin-top: 6pt; margin-bottom: 12pt"><P STYLE="margin: 0pt">&nbsp;</P></DIV>
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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><I>provided, however</I>, that paragraphs (1)(a)(i)
and (1)(a)(ii) do not apply if the information required to be included in a post-effective amendment by those paragraphs is contained
in periodic reports filed with or furnished to the Commission by the Registrant pursuant to Section 13 or Section 15(d) of the Securities
Exchange Act of 1934 that are incorporated by reference in the Registration Statement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">(2)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;That,
for the purpose of determining any liability under the Securities Act of 1933, each such post-effective amendment shall be deemed to be
a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed
to be the initial bona fide offering thereof.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">(3)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;To
remove from registration by means of a post-effective amendment any of the securities being registered which remain unsold at the termination
of the offering.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">(b)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The
undersigned Registrant hereby undertakes that, for purposes of determining any liability under the Securities Act of 1933, each filing
of the Registrant&rsquo;s annual report pursuant to Section 13(a) or Section 15(d) of the Securities Exchange Act of 1934 (and, where
applicable, each filing of an employee benefit plan&rsquo;s annual report pursuant to section 15(d) of the Securities Exchange Act of
1934) that is incorporated by reference in the Registration Statement shall be deemed to be a new registration statement relating to the
securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">(c)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Insofar
as indemnification for liabilities arising under the Securities Act of 1933 may be permitted to directors, officers and controlling persons
of the Registrant pursuant to the foregoing provisions, or otherwise, the Registrant has been advised that in the opinion of the Securities
and Exchange Commission such indemnification is against public policy as expressed in the Act and is, therefore, unenforceable. In the
event that a claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred or paid
by a director, officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding) is asserted
by such director, officer or controlling person in connection with the securities being registered, the Registrant will, unless in the
opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question
whether such indemnification by it is against public policy as expressed in the Act and will be governed by the final adjudication of
such issue.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>


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    <DIV STYLE="break-before: page; margin-top: 6pt; margin-bottom: 12pt"><P STYLE="margin: 0pt">&nbsp;</P></DIV>
    <!-- Field: /Page -->

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SIGNATURES</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">Pursuant to the requirements
of the Securities Act of 1933, the Registrant certifies that it has reasonable grounds to believe that it meets all of the requirements
for filing on Form S-8 and has duly caused the Registration Statement to be signed on its behalf by the undersigned, thereunto duly authorized,
in the Town of DeWitt, State of New York, on the 30<SUP>th</SUP> day of May, 2025.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"></P>

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="border-collapse: collapse; font: 10pt Times New Roman, Times, Serif; width: 100%">
<TR STYLE="vertical-align: top; text-align: left">
  <TD>&nbsp;</TD>
  <TD COLSPAN="2">COMMUNITY FINANCIAL SYSTEM, INC.</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
  <TD STYLE="width: 50%">&nbsp;</TD>
  <TD STYLE="width: 5%">&nbsp;</TD>
  <TD STYLE="width: 45%">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
  <TD>&nbsp;</TD>
  <TD>By: </TD>
  <TD STYLE="border-bottom: Black 1pt solid">/s/ Dimitar A. Karaivanov</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
  <TD>&nbsp;</TD>
  <TD>&nbsp;</TD>
  <TD>Dimitar A. Karaivanov</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
  <TD>&nbsp;</TD>
  <TD>&nbsp;</TD>
  <TD>President and Chief Executive Officer</TD></TR>
</TABLE>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><B>The Plan.</B> Pursuant to the requirements of the Securities Act
of 1933, the Trustees (or other persons who administer the employee benefit plan) have duly caused this registration statement to be signed
on its behalf by the undersigned, thereunto duly authorized, in the Town of DeWitt, State of New York, on the 30<SUP>th</SUP> day of May,
2025.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="border-collapse: collapse; font: 10pt Times New Roman, Times, Serif; width: 100%">
  <TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD COLSPAN="2">COMMUNITY FINANCIAL SYSTEM, INC. 401(k) EMPLOYEE STOCK OWNERSHIP PLAN</TD></TR>
  <TR STYLE="vertical-align: top; text-align: left">
    <TD STYLE="width: 50%">&nbsp;</TD>
    <TD STYLE="width: 5%">&nbsp;</TD>
    <TD STYLE="width: 45%">&nbsp;</TD></TR>
  <TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD COLSPAN="2">Community Bank, N.A., Trustee</TD></TR>
  <TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD>By:</TD>
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Dimitar A. Karaivanov</TD></TR>
  <TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Dimitar A. Karaivanov</TD></TR>
  <TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>President and Chief Executive Officer</TD></TR>
  </TABLE>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><A NAME="a_001"></A><B>POWER OF ATTORNEY</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">KNOW ALL MEN BY THESE PRESENTS,
that each person whose signature appears below constitutes and appoints Dimitar A. Karaivanov and Marya Burgio Wlos, and each of them,
his or her true and lawful attorneys&minus;in&minus;fact and agents, with full power of substitution and re&minus;substitution, for him
or her in his or her name, place and stead, in any and all capacities, to sign any or all amendments to this Registration Statement, and
to file the same, with all exhibits thereto, and all other documents in connection therewith, with the Securities and Exchange Commission,
granting unto said attorneys&minus;in&minus;fact and agents, and each of them, full power and authority to do and perform each and every
act and thing requisite and necessary to be done in and about the premises, as fully to all intents and purposes as he or she might or
could do in person, hereby ratifying and confirming all that said attorneys&minus;in&minus;fact and agents, or any of them, or their or
his or her substitute or substitutes, may lawfully do or cause to be done by virtue thereof.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in"></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">Pursuant to the requirements
of the Securities Act of 1933, this Registration Statement has been signed by the following persons in the capacities and on the dates
indicated.</P>

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    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>SIGNATURE</B></FONT></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>TITLE</B></FONT></TD>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>DATE</B></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>&nbsp;</B></P></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Dimitar A. Karaivanov&#9;&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Dimitar A. Karaivanov</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">President, Chief Executive Officer, and Director (Principal Executive Officer)</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Marya Burgio Wlos&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Marya Burgio Wlos</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Treasurer, Executive Vice President, and Chief Financial Officer (Principal Financial Officer)</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Deresa F. Durkee&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Deresa F. Durkee</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Assistant Treasurer, Senior Vice President, and Chief Accounting Officer (Principal Accounting Officer)</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Eric E. Stickels&#9;&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Eric E. Stickels</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Chair of the Board</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Mark J. Bolus&#9;&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Mark J. Bolus</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Neil E. Fesette&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Neil E. Fesette</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Jeffery J. Knauss&#9;&#9; </U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Jeffery J. Knauss</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Kerrie D. MacPherson&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Kerrie D. MacPherson</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ John Parente&#9;&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">John Parente</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Raymond C. Pecor&#9;&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Raymond C. Pecor, III</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Savneet Singh&#9;&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Savneet Singh</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Sally A. Steele&#9;&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Sally A. Steele</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ Michele P. Sullivan&#9;&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Michele P. Sullivan</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><U>/s/ John F. Whipple, Jr.&#9;</U></P>
    <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">John F. Whipple, Jr.</P></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">May 30, 2025</FONT></TD></TR>
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    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center">&nbsp;</TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD></TR>
  <TR>
    <TD STYLE="width: 40%">&nbsp;</TD>
    <TD STYLE="width: 7%">&nbsp;</TD>
    <TD STYLE="width: 29%">&nbsp;</TD>
    <TD STYLE="width: 24%">&nbsp;</TD></TR>
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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">INDEX TO EXHIBITS</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
  <TR STYLE="vertical-align: top">
    <TD STYLE="width: 11%; padding-right: 5.4pt; padding-left: 5.4pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Exhibit Number</B></FONT></TD>
    <TD STYLE="width: 4%; padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="width: 85%; padding-right: 5.4pt; padding-left: 5.4pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Description of Exhibit</B></FONT></TD></TR>
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    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000110465924062598/tm2414533d1_ex3-1.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">4.1</FONT></A></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000110465924062598/tm2414533d1_ex3-1.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Amended and Restated Certificate of Incorporation of Registrant.&nbsp;&nbsp;Incorporated by reference to Exhibit No. 3.1 to the Current Report on Form 8-K filed with the Commission on May 16, 2024</FONT></A></TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000110465924062598/tm2414533d1_ex3-2.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">4.2</FONT></A></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000110465924062598/tm2414533d1_ex3-2.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Bylaws of Registrant, as amended and restated.&nbsp;&nbsp;Incorporated by reference to Exhibit 3.2 to the Current Report on Form 8-K filed with the Commission on May 16, 2024.</FONT></A></TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000072318813000044/cbnas82013ex45.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">4.3</FONT></A></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="https://www.sec.gov/Archives/edgar/data/723188/000072318813000044/cbnas82013ex45.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Community Financial System, Inc. 401(k) Employee Stock Ownership Plan, dated as of December 20, 2011. Incorporated by reference to Exhibit 4.5 to the Registration Statement on Form S-8 filed on December 20, 2013 (Registration No. 001-13695).</FONT></A></TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="tm2516268d1_ex23-1.htm"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">23.1+</FONT></A></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="tm2516268d1_ex23-1.htm"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Consent of PricewaterhouseCoopers LLP.</FONT></A></TD></TR>
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    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD></TR>
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    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="tm2516268d1_ex-filingfees.htm"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">107</FONT></A></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt"><A HREF="tm2516268d1_ex-filingfees.htm"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Filing fee table</FONT></A></TD></TR>
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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">+ Filed herewith.</P>

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[{"type": "S-8", "sequence": "1", "filename": "tm2516268d1_s8.htm", "description": "FORM S-8", "secsgml_size_bytes": 79842}]
{"company-data": {"conformed-name": "COMMUNITY FINANCIAL SYSTEM, INC.", "cik": "0000723188", "assigned-sic": "6021", "organization-name": "02 Finance", "ein": "161213679", "state-of-incorporation": "DE", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-287702", "film-number": "251012202"}, "business-address": {"street1": "5790 WIDEWATERS PKWY", "city": "DEWITT", "state": "NY", "zip": "13214", "phone": "8007242262"}, "mail-address": {"street1": "5790 WIDEWATERS PARKWAY", "city": "DEWITT", "state": "NY", "zip": "13214"}, "former-company": [{"former-conformed-name": "COMMUNITY BANK SYSTEM, INC.", "date-changed": "20130806"}, {"former-conformed-name": "COMMUNITY BANK NA, a subsidiary of Community Bank System Inc", "date-changed": "20130729"}, {"former-conformed-name": "COMMUNITY BANK NA, a subsidiary of Community Bank System Inc.", "date-changed": "20130726"}]}
As filed with the Securities and Exchange Commission
    on May 30, 2025
Registration No. 333-
UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
FORM S-8
REGISTRATION STATEMENT
UNDER THE SECURITIES ACT OF 1933
(Exact name of registrant as specified in its charter)
Delaware
(State or other jurisdiction
of incorporation or organization)
16-1213679
(I.R.S. Employer
Identification No.)
5790 Widewaters Parkway
Dewitt, New York 13214
(Address of Principal Executive Offices) (Zip Code)
Community Financial System, Inc. 401(k) Employee
    Stock Ownership Plan
(Full title of the plan)
Michael N. Abdo, Esq.
Executive Vice President and General Counsel
5790 Widewaters Parkway
DeWitt, New York 13214
(Name and address of agent for service)
(315) 445-2282
(Telephone number, including area code, of agent
for service)
Indicate by check mark whether the registrant is a large accelerated
filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definitions of
 "large accelerated filer," "accelerated filer," "smaller reporting company," and "emerging growth
company" in Rule 12b-2 of the Exchange Act.
Large
    accelerated filer
x
Accelerated
filer
¨
Non-accelerated
    filer
¨
Smaller reporting company
¨
Emerging growth company
¨
If
an emerging growth company, indicated by check mark if the registration has elected not to use the extended transition period for complying
with any new or revised financial accounting standards provided pursuant to Section 7(a)(2)(B) of the Securities Act.
¨
INTRODUCTION
This Registration Statement
on Form S-8 is filed by Community Financial System, Inc. (the "Registrant") to register an additional 1,500,000 shares of
the Registrant's common stock, par value $1.00 per share ("Common Stock"), which may be issued under the Community Financial
System, Inc. 401(k) Employee Stock Ownership Plan (the "Plan"). We intend to issue the Common Stock with open market purchases.
PART I
INFORMATION REQUIRED IN THE SECTION 10(a) PROSPECTUS
The documents containing the
information required in Part I of Form S-8 will be delivered to participants in the Plan in accordance with Form S−8 and Rule 428(b)
under the Securities Act of 1933, as amended (the "Securities Act"). Such documents are not required to be, and are not, filed
with the Securities and Exchange Commission ("Commission") either as part of this Registration Statement or as prospectuses
or prospectus supplements pursuant to Rule 424 under the Securities Act. These documents and the documents incorporated herein by reference
pursuant to Item 3 of Part II of this Registration Statement, taken together, constitute a prospectus that meets the requirements of Section
10(a) of the Securities Act.
PART II
INFORMATION REQUIRED IN THE REGISTRATION STATEMENT
Item 3.
Incorporation of Documents by Reference
.
The following documents, which
have been filed by the Registrant (Commission File No. 001-13695) with the Commission pursuant to the Securities Exchange Act of 1934
(the "Exchange Act"), are incorporated in this registration statement by reference:
(a) The Registrant's
Annual Report on Form 10−K for the fiscal year ended December 31, 2024, filed with the Commission on
February 28, 2025
.
(b) The Registrant's
Quarterly Report on Form 10−Q for the fiscal quarter ended March 31, 2025, filed with the Commission on
May 9, 2025
.
(c) The Registrant's
Current Reports on Form 8−K filed on
February 14, 2025
,
March 11, 2025
, and
May 23, 2025
.
(d) The portions of the Registrant's
Definitive Proxy Statement on Schedule 14A for the Registrant's 2025 Annual Meeting of Stockholders, filed with the Commission on
March 28, 2025
, that are incorporated by reference into Part III of the Registrant's Annual Report on Form 10-K for the fiscal year
ended December 31, 2024.
(e) The description of the
Company's common stock contained in the Registration Statement on Form 8-A (File No. 001-13695) filed on
December 9, 1997
, including
any amendments or reports filed for the purpose of updating such description.
All documents subsequently
filed by the Registrant pursuant to Sections 13(a), 13(c), 14 and 15(d) of the Exchange Act (other than current reports on Form 8−K
furnished pursuant to Item 2.02 or Item 7.01 of Form 8−K, including any exhibits included with such information, unless otherwise
indicated therein), and prior to the filing of a post−effective amendment which indicates that all securities offered hereby have
been sold or which deregisters all securities then remaining unsold, shall be deemed to be incorporated by reference herein and to be
a part hereof from the date of filing of such documents.
Any statement contained herein
or in a document incorporated or deemed to be incorporated by reference herein shall be deemed to be modified or superseded for purposes
of this registration statement to the extent that a statement contained herein or in any other subsequently filed document which also
is or is deemed to be incorporated by reference herein, or any document forming any part of the Section 10(a) prospectus to be delivered
to participants in connection herewith, modifies or supersedes such statement. Any statement so modified or superseded shall not be deemed,
except as so modified or superseded, to constitute part of this Registration Statement.
2
Item 4.
Description of Securities.
Not applicable.
Item 5.
Interests of Named Experts and Counsel.
Not applicable.
Item 6.
Indemnification of Directors and Officers.
The Registrant is a Delaware
corporation. Section 145 of the Delaware General Corporation Law (the "DGCL") provides that a corporation may indemnify any
person who was or is a party or is threatened to be made a party to any threatened, pending or completed action, suit or proceeding, whether
civil, criminal, administrative or investigative (other than an action by or in the right of the corporation) by reason of the fact that
the person is or was a director, officer, employee, or agent of the corporation, or is or was serving at the request of the corporation
as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise, against expenses
(including attorneys' fees), judgments, fines and amounts paid in settlement actually and reasonably incurred by the person in connection
with such action, suit or proceeding, provided that such person acted in good faith and in a manner reasonably believed to be in, or not
opposed to, the best interests of the corporation, and, with respect to any criminal action or proceeding, had no reasonable cause to
believe that his or her conduct was unlawful.
This power to indemnify applies
to actions or suits brought by or in the right of the corporation to procure a judgment in its favor as well, but only to the extent of
expenses (including attorneys' fees but excluding amounts paid in settlement) actually and reasonably incurred by the person in
connection with the defense or settlement of such action or suit if such person acted in good faith and in a manner reasonably believed
to be in, or not opposed to, the best interests of the corporation, except that no indemnification shall be made in respect of any claim,
issue or matter as to which such person shall have been adjudged to be liable to the corporation, unless and only to the extent that the
Delaware Court of Chancery or the court in which such action was brought shall determine upon application that, despite the adjudication
of liability but in view of all the circumstances of the case, such person is fairly and reasonably entitled to indemnity for such expenses
which the court shall deem proper.
Section 145 of the DGCL further
provides that to the extent a director or officer of a corporation has been successful in the defense of any action, suit or proceeding
referred to in subsections (a) and (b) of Section 145, or in the defense of any claim, issue or matter therein, he or she shall be indemnified
against expenses (including attorneys' fees) actually and reasonably incurred by him or her in connection therewith; that indemnification
provided for by Section 145 shall not be deemed exclusive of any other rights to which the indemnified party may be entitled; and that
the corporation shall have power to purchase and maintain insurance on behalf of a director or officer of the corporation against any
liability asserted against him or her or incurred by him or her in any such capacity or arising out of his or her status as such whether
or not the corporation would have the power to indemnify him or her against such liabilities under Section 145.
Article 9 of the Registrant's
Amended and Restated Certificate of Incorporation provides that the Registrant's directors shall not be liable to the Registrant
or its shareholders for monetary damages as a result of breach of fiduciary duty, except for liability in connection with a breach of
a director's duty of loyalty, for acts or omissions not in good faith or involving intentional misconduct or a knowing violation
of the law, for a transaction from which a director derives an improper personal benefit, or for liability arising under Section 174 of
the DGCL.
Article 7 of the Registrant's
Bylaws provides that the Registrant shall indemnify any person made, or threatened to be made, a party to an action, suit or proceeding,
whether criminal, civil, administrative or investigative, by reason of the fact that he or she is or was a director or officer of the
registrant against expenses (including attorney's fees), judgments, fines and amounts paid in settlement, to the fullest extent
and in the manner set forth in and permitted by the DGCL, and any other applicable law, as from time to time in effect.
The Registrant is insured
against liabilities it may incur by reason of its indemnification of officers and directors in accordance with its Bylaws. In addition,
as permitted under Delaware law, the Registrant maintains liability insurance covering directors and officers of the Registrant and its
subsidiaries.
The foregoing summaries are
necessarily subject to the complete texts of Section 145 of the DGCL, the Registrant's Certificate of Incorporation, as amended,
and the Registrant's Bylaws, as amended, referred to above and are qualified in their entirety by reference thereto.
3
Item 7.
Exemption from Registration Claimed.
Not applicable.
Item 8.
Exhibits.
4.1
Amended and Restated Certificate of Incorporation of Registrant. Incorporated by
reference to Exhibit No. 3.1 to the Current Report on Form 8-K filed with the Commission on May 16, 2024.
4.2
Bylaws of Registrant, as amended and restated. Incorporated by reference to Exhibit
3.2 to the Current Report on Form 8-K filed with the Commission on May 16, 2024.
4.3
Community Financial System, Inc. 401(k) Employee Stock Ownership Plan, dated as
of December 20, 2011. Incorporated by reference to Exhibit 4.5 to the Registration Statement on Form S-8 filed on December 20, 2013 (Registration
No. 001-13695).
23.1
Consent of PricewaterhouseCoopers LLP.
24.1
Power of Attorney (contained on the Signature Page of this registration statement).
107
Filing fee table
Item 9.
Undertakings.
(a)       The
undersigned Registrant hereby undertakes:
(1)       To
file, during any period in which offers or sales are being made, a post-effective amendment to this Registration Statement:
(i)
To include any prospectus required by Section 10(a)(3) of the Securities Act of 1933;
(ii)
To reflect in the prospectus any facts or events arising after the effective date of the Registration
Statement (or the most recent post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change
in the information set forth in the Registration Statement; and
(iii)
To include any material information with respect to the plan of distribution not previously disclosed
in the Registration Statement or any material change to such information in the Registration Statement;
4
provided, however
, that paragraphs (1)(a)(i)
and (1)(a)(ii) do not apply if the information required to be included in a post-effective amendment by those paragraphs is contained
in periodic reports filed with or furnished to the Commission by the Registrant pursuant to Section 13 or Section 15(d) of the Securities
Exchange Act of 1934 that are incorporated by reference in the Registration Statement.
(2)       That,
for the purpose of determining any liability under the Securities Act of 1933, each such post-effective amendment shall be deemed to be
a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed
to be the initial bona fide offering thereof.
(3)       To
remove from registration by means of a post-effective amendment any of the securities being registered which remain unsold at the termination
of the offering.
(b)       The
undersigned Registrant hereby undertakes that, for purposes of determining any liability under the Securities Act of 1933, each filing
of the Registrant's annual report pursuant to Section 13(a) or Section 15(d) of the Securities Exchange Act of 1934 (and, where
applicable, each filing of an employee benefit plan's annual report pursuant to section 15(d) of the Securities Exchange Act of
1934) that is incorporated by reference in the Registration Statement shall be deemed to be a new registration statement relating to the
securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.
(c)       Insofar
as indemnification for liabilities arising under the Securities Act of 1933 may be permitted to directors, officers and controlling persons
of the Registrant pursuant to the foregoing provisions, or otherwise, the Registrant has been advised that in the opinion of the Securities
and Exchange Commission such indemnification is against public policy as expressed in the Act and is, therefore, unenforceable. In the
event that a claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred or paid
by a director, officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding) is asserted
by such director, officer or controlling person in connection with the securities being registered, the Registrant will, unless in the
opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question
whether such indemnification by it is against public policy as expressed in the Act and will be governed by the final adjudication of
such issue.
5
SIGNATURES
Pursuant to the requirements
of the Securities Act of 1933, the Registrant certifies that it has reasonable grounds to believe that it meets all of the requirements
for filing on Form S-8 and has duly caused the Registration Statement to be signed on its behalf by the undersigned, thereunto duly authorized,
in the Town of DeWitt, State of New York, on the 30
th
day of May, 2025.
COMMUNITY FINANCIAL SYSTEM, INC.
By:
/s/ Dimitar A. Karaivanov
Dimitar A. Karaivanov
President and Chief Executive Officer
The Plan.
Pursuant to the requirements of the Securities Act
of 1933, the Trustees (or other persons who administer the employee benefit plan) have duly caused this registration statement to be signed
on its behalf by the undersigned, thereunto duly authorized, in the Town of DeWitt, State of New York, on the 30
th
day of May,
2025.
COMMUNITY FINANCIAL SYSTEM, INC. 401(k) EMPLOYEE STOCK OWNERSHIP PLAN
Community Bank, N.A., Trustee
By:
/s/ Dimitar A. Karaivanov
Dimitar A. Karaivanov
President and Chief Executive Officer
POWER OF ATTORNEY
KNOW ALL MEN BY THESE PRESENTS,
that each person whose signature appears below constitutes and appoints Dimitar A. Karaivanov and Marya Burgio Wlos, and each of them,
his or her true and lawful attorneys−in−fact and agents, with full power of substitution and re−substitution, for him
or her in his or her name, place and stead, in any and all capacities, to sign any or all amendments to this Registration Statement, and
to file the same, with all exhibits thereto, and all other documents in connection therewith, with the Securities and Exchange Commission,
granting unto said attorneys−in−fact and agents, and each of them, full power and authority to do and perform each and every
act and thing requisite and necessary to be done in and about the premises, as fully to all intents and purposes as he or she might or
could do in person, hereby ratifying and confirming all that said attorneys−in−fact and agents, or any of them, or their or
his or her substitute or substitutes, may lawfully do or cause to be done by virtue thereof.
6
Pursuant to the requirements
of the Securities Act of 1933, this Registration Statement has been signed by the following persons in the capacities and on the dates
indicated.
SIGNATURE
TITLE
DATE
/s/ Dimitar A. Karaivanov
Dimitar A. Karaivanov
President, Chief Executive Officer, and Director (Principal Executive Officer)
May 30, 2025
/s/ Marya Burgio Wlos
Marya Burgio Wlos
Treasurer, Executive Vice President, and Chief Financial Officer (Principal Financial Officer)
May 30, 2025
/s/ Deresa F. Durkee
Deresa F. Durkee
Assistant Treasurer, Senior Vice President, and Chief Accounting Officer (Principal Accounting Officer)
May 30, 2025
/s/ Eric E. Stickels
Eric E. Stickels
Chair of the Board
May 30, 2025
/s/ Mark J. Bolus
Mark J. Bolus
Director
May 30, 2025
/s/ Neil E. Fesette
Neil E. Fesette
Director
May 30, 2025
/s/ Jeffery J. Knauss
Jeffery J. Knauss
Director
May 30, 2025
/s/ Kerrie D. MacPherson
Kerrie D. MacPherson
Director
May 30, 2025
/s/ John Parente
John Parente
Director
May 30, 2025
/s/ Raymond C. Pecor
Raymond C. Pecor, III
Director
May 30, 2025
/s/ Savneet Singh
Savneet Singh
Director
May 30, 2025
/s/ Sally A. Steele
Sally A. Steele
Director
May 30, 2025
/s/ Michele P. Sullivan
Michele P. Sullivan
Director
May 30, 2025
/s/ John F. Whipple, Jr.
John F. Whipple, Jr.
Director
May 30, 2025
7
INDEX TO EXHIBITS
Exhibit Number
Description of Exhibit
4.1
Amended and Restated Certificate of Incorporation of Registrant.  Incorporated by reference to Exhibit No. 3.1 to the Current Report on Form 8-K filed with the Commission on May 16, 2024
4.2
Bylaws of Registrant, as amended and restated.  Incorporated by reference to Exhibit 3.2 to the Current Report on Form 8-K filed with the Commission on May 16, 2024.
4.3
Community Financial System, Inc. 401(k) Employee Stock Ownership Plan, dated as of December 20, 2011. Incorporated by reference to Exhibit 4.5 to the Registration Statement on Form S-8 filed on December 20, 2013 (Registration No. 001-13695).
23.1+
Consent of PricewaterhouseCoopers LLP.
107
Filing fee table
+ Filed herewith.
8