<SEC-DOCUMENT>0001104659-25-059935.txt : 20250616
<SEC-HEADER>0001104659-25-059935.hdr.sgml : 20250616
<ACCEPTANCE-DATETIME>20250616165627
ACCESSION NUMBER:		0001104659-25-059935
CONFORMED SUBMISSION TYPE:	DEFA14A
PUBLIC DOCUMENT COUNT:		1
FILED AS OF DATE:		20250616
DATE AS OF CHANGE:		20250616

FILER:

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			CANTALOUPE, INC.
		CENTRAL INDEX KEY:			0000896429
		STANDARD INDUSTRIAL CLASSIFICATION:	CALCULATING & ACCOUNTING MACHINES (NO ELECTRONIC COMPUTERS) [3578]
		ORGANIZATION NAME:           	06 Technology
		EIN:				232679963
		STATE OF INCORPORATION:			PA
		FISCAL YEAR END:			0630

	FILING VALUES:
		FORM TYPE:		DEFA14A
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-33365
		FILM NUMBER:		251050878

	BUSINESS ADDRESS:	
		STREET 1:		101 LINDENWOOD DRIVE
		STREET 2:		SUITE 405
		CITY:			MALVERN
		STATE:			PA
		ZIP:			19355
		BUSINESS PHONE:		8006330340

	MAIL ADDRESS:	
		STREET 1:		101 LINDENWOOD DRIVE
		STREET 2:		SUITE 405
		CITY:			MALVERN
		STATE:			PA
		ZIP:			19355

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	USA TECHNOLOGIES INC
		DATE OF NAME CHANGE:	19950523

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	USA ENTERTAINMENT CENTER INC
		DATE OF NAME CHANGE:	19931029
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<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>UNITED STATES </B></P>

<P STYLE="font: 18pt 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>

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<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SCHEDULE 14A </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: center"><B>Proxy Statement Pursuant to Section 14(a) of
the </B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Securities Exchange Act of 1934 </B></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">Filed by the Registrant <FONT STYLE="font-family: Wingdings">&#120;</FONT></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">Filed by a Party other than the Registrant <FONT STYLE="font-family: Wingdings">&#168;</FONT></P>

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

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    <TD STYLE="font-size: 10pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Preliminary Proxy Statement </FONT></TD></TR>
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    <TD STYLE="font-size: 10pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))</B></FONT><FONT STYLE="font-size: 10pt">&nbsp;</FONT></TD></TR>
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    <TD STYLE="font-size: 10pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Definitive Proxy Statement </FONT></TD></TR>
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    <TD STYLE="font-size: 10pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Definitive Additional Materials </FONT></TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

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    <TD STYLE="font-size: 10pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Soliciting Material under Rule 14a-12&nbsp;</FONT></TD></TR>
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<P STYLE="margin-top: 0; margin-bottom: 0">&nbsp;</P>
<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Cantaloupe, Inc. </B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>(Name of registrant as specified in its charter)
</B></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>(Name of person(s) filing proxy statement, if
other than the registrant) </B></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">Payment of Filing Fee (Check all boxes that apply):</P>

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    <TD STYLE="font-size: 10pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">No fee required.</FONT></TD></TR>
  </TABLE>
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    <TD STYLE="font-size: 10pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Fee paid previously with preliminary materials </FONT></TD></TR>
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    <TD STYLE="font-size: 10pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11&nbsp;</FONT></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">On June 16, 2025, Ravi Venkatesan, the CEO of Cantaloupe, Inc. (&ldquo;Cantaloupe&rdquo;),
emailed the below communications related to the proposed acquisition of the Company by 365 Retail Markets, LLC, a Delaware limited liability
company (&ldquo;365&rdquo;), pursuant to the Agreement and Plan of Merger, dated as of June 15, 2025, by and among, <I>inter alia</I>,
Cantaloupe and 365:</P>

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

<P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0pt 0"><B>CTLP Template Mailer for High Priority Clients
</B></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"><FONT STYLE="font-family: Times New Roman, Times, Serif"><B>Subject</B></FONT>:
Cantaloupe + 365 Retail Markets: Strengthening Our Solutions for You</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">Dear [Customer Name],</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">As one of our most valued partners, I wanted to reach out today to
share some exciting news. Today, Cantaloupe has entered into an agreement to be acquired by 365 Retail Markets, creating a strategic partnership
that significantly expands what we can deliver to your organization.</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">I know that as a key partner, you&rsquo;ve come to rely on Cantaloupe
for our reliability, innovation, and unwavering commitment to your success. I want to personally assure you that this commitment not only
remains unchanged, it's also about to be dramatically strengthened.</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">This transaction represents an opportunity to combine Cantaloupe&rsquo;s
offerings in payments, telemetry, and vertical-specific software solutions with 365&rsquo;s deep expertise and focus in micro markets,
dining solutions, and POS technologies. For your business, this means access to a comprehensive, end-to-end unattended retail platform
that can address every aspect of your self-service commerce needs &ndash; from hardware and software to payment processing technology
and data analytics &ndash; under one partnership.</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">The combined company&rsquo;s diversified portfolio will allow us to
better serve both foodservice operator (FSO) and non-FSO customers across convenience services, retail, hospitality, and sports and entertainment
&ndash; growing our footprint across North America, Latin America and Europe. With the meaningful synergies unleashed through this transaction,
we gain opportunities to further invest in our business and deliver cost savings for our customers.</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">The transaction is expected to close in the second half of 2025, pending
all necessary approvals. In the meantime, it's business as usual, and we'll keep you informed of key milestones along the way.</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">Given the value of our partnership, I wanted to ensure you heard this
news directly from me and had the opportunity to discuss any questions. We will be reaching out to schedule a dedicated conversation about
how this transaction specifically benefits your organization and to discuss any new opportunities this partnership might unlock.</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">This is more than a business combination - it's about strengthening
our ability to be your trusted partner in driving growth and innovation. We are excited about what we can accomplish together with these
expanded capabilities.</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">Thank you for your continued partnership and trust in Cantaloupe. I
look forward to our continued collaboration and the exciting opportunities ahead.</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">Please see here the press release we just issued for more details.</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">With appreciation,</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">&nbsp;</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">CEO, Cantaloupe, Inc.</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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<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"><B>Cautionary Statement Regarding Forward-Looking Statements</B></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">This communication contains &ldquo;forward-looking statements&rdquo;,
as that term is defined under the Private Securities Litigation Reform Act of 1995 and other securities laws, regarding Cantaloupe, Inc.
(&ldquo;Cantaloupe&rdquo;) and 365 Retail Markets, LLC (&ldquo;365&rdquo;) and the potential transaction between Cantaloupe and 365, including,
but not limited to, statements about the strategic rationale and benefits of the proposed transaction between Cantaloupe and 365, including
future financial and operating results, Cantaloupe&rsquo;s or 365&rsquo;s plans, objectives, expectations and intentions and the expected
timing of completion of the proposed transaction. You can generally identify forward-looking statements by the use of forward-looking
terminology such as &ldquo;anticipate&rdquo;, &ldquo;believe&rdquo;, &ldquo;continue&rdquo;, &ldquo;could&rdquo;, &ldquo;estimate&rdquo;,
&ldquo;expect&rdquo;, &ldquo;explore&rdquo;, &ldquo;evaluate&rdquo;, &ldquo;forecast&rdquo;, &ldquo;intend&rdquo;, &ldquo;may&rdquo;,
&ldquo;might&rdquo;, &ldquo;plan&rdquo;, &ldquo;potential&rdquo;, &ldquo;predict&rdquo;, &ldquo;project&rdquo;, &ldquo;seek&rdquo;, &ldquo;should&rdquo;,
&ldquo;targeted&rdquo;, &ldquo;will&rdquo; or &ldquo;would&rdquo;, or the negative thereof or other variations thereon or comparable terminology.
These forward-looking statements are based on each of the companies&rsquo; current plans, objectives, estimates, expectations and intentions
and inherently involve significant risks and uncertainties, many of which are beyond Cantaloupe&rsquo;s or 365&rsquo;s control. Although
we believe the expectations reflected in any forward-looking statements are based on reasonable assumptions, we can give no assurance
that our expectations will be attained, and therefore actual results and the timing of events could differ materially from those anticipated
in such forward-looking statements as a result of these risks and uncertainties, which include, without limitation, risks and uncertainties
associated with: Cantaloupe&rsquo;s and 365&rsquo;s ability to complete the potential transaction on the proposed terms or on the anticipated
timeline, or at all, including risks and uncertainties related to securing the necessary regulatory approvals and the approval of Cantaloupe&rsquo;s
shareholders and the satisfaction of other closing conditions to consummate the proposed transaction; the possibility that competing offers
or acquisition proposals for Cantaloupe will be made; the occurrence of any event, change or other circumstance that could give rise to
the termination of the definitive merger agreement relating to the proposed transaction, including in circumstances which would require
Cantaloupe to pay a termination fee; failure to realize the expected benefits of the proposed transaction; significant transaction costs
and/or unknown or inestimable liabilities; the risk that Cantaloupe&rsquo;s business will not be integrated successfully, including with
respect to implementing systems to prevent a material security breach of any internal systems or to successfully manage credit and fraud
risks in business units, or that such integration may be more difficult, time-consuming or costly than expected; 365&rsquo;s ability to
obtain the expected financing to consummate the proposed transaction, and the continued availability of capital and financing for 365
following the proposed transaction; risks related to future opportunities and plans for the combined company, including the uncertainty
of expected future regulatory filings, financial performance and results of the combined company following completion of the proposed
transaction; disruption from the proposed transaction, making it more difficult to conduct business as usual or maintain relationships
with customers, employees or suppliers, including as it relates to Cantaloupe&rsquo;s ability to successfully renew existing client contracts
on favorable terms or at all and obtain new clients; the ability of Cantaloupe to retain and hire key personnel; the diversion of management&rsquo;s
attention from ongoing business operations; the business, economic and political conditions in the markets in which Cantaloupe operates;
the impact of new or changes in current laws, regulations, credit card association rules or other industry standards, including privacy
and cybersecurity laws and regulations; effects relating to the announcement of the proposed transaction or any further announcements
or the consummation of the potential transaction on the market price of Cantaloupe&rsquo;s securities; the risk of potential shareholder
litigation associated with the potential transaction, including resulting expense or delay; regulatory initiatives and changes in tax
laws; the impact of pandemics or other events on the operations and financial results of Cantaloupe or the combined company; general economic
conditions; and other risks and uncertainties affecting Cantaloupe and 365, including those described from time to time under the caption
&ldquo;Risk Factors&rdquo; or &ldquo;Management&rsquo;s Discussion and Analysis of Financial Condition and Results of Operations&rdquo;
and elsewhere in Cantaloupe&rsquo;s Securities and Exchange Commission (&ldquo;SEC&rdquo;) filings and reports, including Cantaloupe&rsquo;s
Annual Report on Form 10-K for the year ended June 30, 2024, Quarterly Report on Form 10-Q for the quarter ended September 30, 2024, Quarterly
Report on Form 10-Q for the quarter ended December 31, 2024 and Quarterly Report on Form 10-Q for the quarter ended March 31, 2025, as
well as in subsequent Current Reports on Form 8-K and other filings and reports by Cantaloupe. Moreover, other risks and uncertainties
of which Cantaloupe or 365 are not currently aware may also affect each of the companies&rsquo; forward-looking statements and may cause
actual results and the timing of events to differ materially from those anticipated. Cantaloupe and 365 caution investors that such forward-looking
statements are not guarantees of future performance and that undue reliance should not be placed on such forward-looking statements. The
forward-looking statements made in this communication are made only as of the date hereof or as of the dates indicated in the forward-looking
statements and reflect the views stated therein with respect to future events as at such dates, even if they are subsequently made available
by Cantaloupe or 365 on their respective websites or otherwise. Neither Cantaloupe nor 365 undertakes any obligation to update or supplement
any forward-looking statements to reflect actual results, new information, future events, changes in its expectations or other circumstances
that exist after the date as of which the forward-looking statements were made.</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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<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"><B>Additional Information and Where to Find It</B></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">This communication is being made in connection with the proposed transaction
between Cantaloupe and 365. In connection with the proposed transaction, Cantaloupe intends to file a proxy statement with the SEC in
preliminary and definitive form. Cantaloupe may also file other relevant documents with the SEC regarding the proposed transaction. The
information in the preliminary proxy statement will not be complete and may be changed. The definitive proxy statement (when available)
will be mailed to shareholders of Cantaloupe. This communication is not a substitute for any proxy statement or any other document that
may be filed with the SEC or sent to Cantaloupe&rsquo;s shareholders in connection with the proposed transaction.</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">INVESTORS AND SECURITY HOLDERS OF CANTALOUPE ARE URGED TO READ THE
PROXY STATEMENT AND ANY OTHER RELEVANT DOCUMENTS THAT MAY BE FILED WITH THE SEC, AS WELL AS ANY AMENDMENTS OR SUPPLEMENTS TO THESE DOCUMENTS,
CAREFULLY AND IN THEIR ENTIRETY IF AND WHEN THEY BECOME AVAILABLE BECAUSE THEY CONTAIN OR WILL CONTAIN IMPORTANT INFORMATION ABOUT CANTALOUPE,
365 AND THE PROPOSED TRANSACTION.</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">Investors and security holders will be able to obtain free copies of
the preliminary proxy statement and the definitive proxy statement (in each case, if and when available) and other documents containing
important information about Cantaloupe and the proposed transaction once such documents are filed with the SEC through the website maintained
by the SEC at www.sec.gov. Copies of the documents filed with the SEC by Cantaloupe are available free of charge on Cantaloupe&rsquo;s
website at cantaloupeinc.gcs-web.com.</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"><B>Participants in the Solicitation</B></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">Cantaloupe and its directors, executive officers and other members
of management and employees may, under the rules of the SEC, be deemed to be participants in the solicitation of proxies from Cantaloupe&rsquo;s
shareholders in connection with the proposed transaction. Information about the directors and executive officers of Cantaloupe and their
ownership of Cantaloupe&rsquo;s securities is set forth in the definitive proxy statement for Cantaloupe&rsquo;s 2025 Annual Meeting of
Shareholders (https://www.sec.gov/Archives/edgar/data/896429/000162828024042315/ctlp-20241004.htm), which was filed with the SEC on October
4, 2024 (the &ldquo;Annual Meeting Proxy Statement&rdquo;), including under the sections entitled &ldquo;Director Compensation Program&rdquo;,
&ldquo;Fiscal Year 2024 Director Compensation&rdquo;, &ldquo;Fiscal Year 2024 Executive Compensation&rdquo;, &ldquo;Executive Officer
Employment Arrangements&rdquo;, &ldquo;Summary Compensation Table&rdquo;, &ldquo;Grant of Plan-Based Awards&rdquo;, &ldquo;Outstanding
Equity Awards at Fiscal Year-End&rdquo;, &ldquo;Option Exercises and Stock Vested&rdquo;, &ldquo;Potential Payments Upon Termination or
Change of Control&rdquo;, &ldquo;CEO Pay Ratio Disclosure&rdquo;, &ldquo;Pay Versus Performance&rdquo; and &ldquo;Security Ownership of
Certain Beneficial Owners and Management&rdquo; and Cantaloupe&rsquo;s Annual Report on Form 10-K for the year ended June 30, 2024 (https://www.sec.gov/Archives/edgar/data/896429/000162828024040037/ctlp-20240630.htm),
which was filed with the SEC on September 10, 2024, including under the sections entitled &ldquo;Item 10. Directors, Executive Officers
and Corporate Governance&rdquo;, &ldquo;Item 11. Executive Compensation&rdquo;, &ldquo;Item 12. Security Ownership of Certain Beneficial
Owners and Management and Related Shareholder Matters&rdquo; and &ldquo;Item 13. Certain Relationships and Related Transactions, and Director
Independence&rdquo;. To the extent holdings of Cantaloupe&rsquo;s securities by such directors or executive officers (or the identity
of such directors or executive officers) have changed since the information set forth in the Annual Meeting Proxy Statement, such information
has been or will be reflected on the Initial Statements of Beneficial Ownership on Form 3 or Statements of Changes in Beneficial Ownership
on Form 4 filed with the SEC. Additional information regarding the interests of Cantaloupe&rsquo;s directors and executive officers in
the proposed transaction, which may, in some cases, be different than those of Cantaloupe&rsquo;s shareholders generally, will be included
in the proxy statement relating to the transaction if and when it is filed with the SEC. You may obtain free copies of these documents
using the sources indicated above.</P>

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