Other than as described herein, this Supplement does not change the proposals to be acted on at the Annual Meeting or the
recommendation of the Board with respect to such proposals. Proposal 4 will be voted separately from Proposal 1. The 10
nominees who receive the largest number of affirmative votes cast on Proposal 1 at the Annual Meeting will be elected as
directors, and the nominee who receives the largest number of affirmative votes cast on Proposal 4 at the Annual Meeting will
be elected as a director. Under Associated’s Corporate Governance Guidelines, any nominee in an uncontested election who
receives a greater number of votes “withheld” from than votes “FOR” his or her election is required to tender his or her
resignation following certification of the shareholder vote. The Corporate Governance and Social Responsibility Committee is
required to make a recommendation to the Board with respect to any such letter of resignation, and the Board is required to take
action with respect to this recommendation and to disclose its decision and decision-making process. Votes that are withheld
will be treated as shares that are present and entitled to vote for purposes of determining the presence of a quorum but as
unvoted for purposes of determining the approval of any matter submitted to shareholders for a vote. If a broker indicates on
the proxy that it does not have discretionary authority as to certain shares to vote on a particular matter, those shares will not be
considered as present and entitled to vote with respect to that matter but will be considered as present and entitled to vote for
purposes of determining the presence of a quorum for the meeting. Votes that are withheld and Broker Non-Votes will have no
effect on the outcome of the vote for Proposal 1 and Proposal 4.
YOUR VOTE IS IMPORTANT.
If you have already submitted a proxy or voted, you are not required to submit a new proxy or vote again. However, you are
encouraged to vote your shares as soon as possible using the amended proxy card enclosed with this Supplement or
through one of the other methods described below, which will enable you to vote on Ms. Kotouc under Proposal 4 or if
you have not voted yet. The amended proxy card enclosed with this Supplement differs from the proxy card previously
furnished to you in that the amended proxy card includes Ms. Kotouc as a nominee for director under Proposal 4.
Even if you have already voted, we encourage you to resubmit your vote on all proposals.
Shareholders are urged to vote as promptly as possible by Internet or telephone, or by signing, dating, and returning the
amended proxy card in the envelope provided. If no specification is made for Proposal 1, the shares will be voted “FOR” the
election of the Board’s nominees for director. If no specification is made for Proposals 2 or 3, the shares will be voted in
accordance with the Board’s recommendation for each of the proposals as stated on page 2 of the Proxy Statement. If no
specification is made for Proposal 4, the shares will be voted “FOR” the election of Ms. Kotouc.
VOTE BY INTERNET - www.proxyvote.com. Use the Internet to transmit your voting instructions and for electronic delivery
of information up until 11:59 p.m. Eastern Time on April 27, 2026. Have your amended proxy card in hand when you access
the website and follow the instructions to obtain your records and to create an electronic voting instruction form. You will be
required to enter the unique control number imprinted on your amended proxy card in order to vote online. The Internet voting
procedures are designed to authenticate shareholders’ identities, to allow shareholders to provide their voting instructions, and
to confirm that shareholders’ instructions have been recorded properly. You should be aware that there might be costs
associated with your electronic access, such as usage charges from Internet access providers and telephone companies. If you
vote by Internet, please do not mail your amended proxy card.
VOTE BY TELEPHONE - 1-800-690-6903. Use any touch-tone telephone to transmit your voting instructions no later than
11:59 p.m. Eastern Time on April 27, 2026. Have your amended proxy card in hand when you call and then follow the
instructions. If you vote by telephone, please do not mail your amended proxy card.
AT THE VIRTUAL ANNUAL MEETING - You also may vote online during the Annual Meeting by following the
instructions provided on the meeting website during the Annual Meeting. For additional information, see the section entitled
“Virtual Meeting Information” on page 3 of the Proxy Statement.
Proxies may be revoked at any time prior to the time they are exercised by filing with the Corporate Secretary of Associated a
written revocation or a duly executed proxy bearing a later date, or by voting at the Annual Meeting via the meeting platform.
Proxies may not be revoked by telephone, and may not be revoked via the Internet prior to the Annual Meeting. The Corporate
Secretary of Associated is Randall J. Erickson, 433 Main Street, Green Bay, Wisconsin 54301. However, if you return, or have