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Letter to Cantaloupe’s Shareholders

from Cantaloupe’s Chief Executive Officer and Director

and Cantaloupe’s Chairman of the Board of Directors

You are cordially invited to attend a special meeting (which, including any adjournments or postponements thereof, we refer to as the “Special Meeting”) of the shareholders of Cantaloupe, Inc. (which we refer to as “Cantaloupe”) to be held on [ ], 2025, at [ ], Eastern time, virtually at www.virtualshareholdermeeting.com/CTLP2025SM.

At the Special Meeting, Cantaloupe will ask you to vote on a proposal to approve and adopt the Agreement and Plan of Merger, dated as of June 15, 2025, by and among Cantaloupe, 365 Retail Markets, LLC (which we refer to as “365”), Catalyst Holdco I, Inc. (which we refer to as “Holdco”), Catalyst Holdco II, Inc. (which we refer to as “Holdco II”) and Catalyst MergerSub Inc. (which we refer to as “Merger Subsidiary”), as it may be amended from time to time (which we refer to as the “Merger Agreement”), under which Merger Subsidiary will merge with and into Cantaloupe, with Cantaloupe surviving the merger (which we refer to as the “Merger”) as a wholly owned subsidiary of Holdco II.

If the Merger is completed, at the effective time of the Merger, each share of common stock, without par value, of Cantaloupe (which we refer to as “common stock”) issued and outstanding immediately prior to the effective time of the Merger (but excluding certain shares as set forth in the Merger Agreement) will be converted into the right to receive $11.20 in cash, without interest and less any applicable withholding taxes.

After careful consideration, Cantaloupe’s board of directors (which we refer to as the “Board” or “Cantaloupe’s Board”) unanimously (i) determined that the Merger Agreement and the transactions contemplated thereby, including the Merger, are in the best interests of Cantaloupe, (ii) approved, adopted and declared advisable the Merger Agreement and the transactions contemplated thereby, including the Merger, (iii) recommended the approval and adoption of the Merger Agreement by Cantaloupe’s shareholders and (iv) directed that the Merger Agreement be submitted to Cantaloupe’s shareholders for their vote to adopt the Merger Agreement at a duly convened meeting of Cantaloupe’s shareholders.

The Board unanimously recommends that you vote “FOR” the proposal to approve and adopt the Merger Agreement, including the Merger, which proposal Cantaloupe refers to as the “Merger Proposal”.

At the Special Meeting, Cantaloupe will also ask you (i) to approve, on a non-binding, advisory basis, the compensation that will or may become payable to Cantaloupe’s named executive officers in connection with the Merger, which proposal Cantaloupe refers to as the “Advisory Compensation Proposal” and (ii) to approve the adjournment of the Special Meeting from time to time, if necessary or appropriate (as determined by the Board or the chairperson of the meeting) to solicit additional proxies to vote in favor of the proposal to approve and adopt the Merger Agreement, in the event that there are insufficient votes at the time of the Special Meeting to establish a quorum or approve and adopt the Merger Agreement or with 365’s prior written consent, which proposal Cantaloupe refers to as the “Adjournment Proposal”.

The Board unanimously recommends that you vote “FOR” the Advisory Compensation Proposal and that you vote “FOR” the Adjournment Proposal.

As of [ ], 2025 (which we refer to as the “record date”), we had outstanding [ ] shares of common stock and [ ] shares of Series A Convertible Preferred Stock (which we refer to as “preferred stock” and, together with common stock, “Cantaloupe stock”).

Each member of the Board and Hudson Executive Capital LP, collectively representing approximately [ ]% of the voting power of the shares of Cantaloupe stock outstanding as of the record date and entitled to vote at the Special Meeting, have entered into Voting Agreements with 365 to, among other things, vote in favor of the proposals set forth in this proxy statement. For more information, see the section of this proxy statement titled “The Merger—Voting Agreements”.

Your vote is very important, regardless of the number of shares you own. Cantaloupe cannot complete the Merger without the affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon, voting together as a

single class. Each share of common stock outstanding as of the record date will be entitled to one vote on each matter submitted to our shareholders for approval at the Special Meeting. Each share of preferred stock outstanding as of the record date will be entitled to vote on an as-converted basis, with each share of preferred stock outstanding as of the record date entitling the holder thereof to 0.1988 of a vote on each matter submitted to our shareholders for approval at the Special Meeting (with any fractional vote determined on an aggregate conversion basis being rounded to the nearest whole number).

In the materials accompanying this letter, you will find a Notice of Special Meeting of shareholders, a proxy statement relating to the actions to be taken by Cantaloupe’s shareholders at the Special Meeting or any adjournment or postponement thereof and a proxy card. The proxy statement includes other important information about the Merger Agreement and the Merger. Cantaloupe encourages you to read the entire proxy statement and its annexes carefully. A copy of the Merger Agreement is attached as Annex A to the accompanying proxy statement. You may also obtain additional information about Cantaloupe from documents Cantaloupe has filed with the Securities and Exchange Commission.

WHETHER OR NOT YOU PLAN TO ATTEND THE SPECIAL MEETING, WE ENCOURAGE YOU TO SUBMIT YOUR PROXY AS PROMPTLY AS POSSIBLE BY TELEPHONE, OVER THE INTERNET OR BY COMPLETING, SIGNING AND RETURNING YOUR PROXY CARD IN THE ENCLOSED ENVELOPE AS PROMPTLY AS POSSIBLE AS INSTRUCTED IN THESE MATERIALS. It is important that your shares be represented and voted at the Special Meeting. If you are a shareholder of record, you may vote at the Special Meeting as you wish, even if you have previously returned your proxy card, and your vote will revoke any proxy that you have previously submitted. If your shares are held in the name of your bank, broker or other nominee, you must obtain a proxy, executed in your favor, from the holder of record to be able to vote at the Special Meeting. If your shares are held in street name by your bank, broker or other nominee, you should follow the directions provided by your bank, broker or other nominee regarding how to vote your shares of Cantaloupe stock.

On behalf of the entire Board we thank you, Cantaloupe’s shareholders, for your support and investment in Cantaloupe.

Neither the U.S. Securities and Exchange Commission nor any state securities regulatory agency has approved or disapproved of the Merger, passed upon the merits of the Merger Agreement or the Merger or determined if the disclosure in the accompanying proxy statement is accurate or complete. Any representation to the contrary is a criminal offense.

The accompanying proxy statement is dated [ ], 2025, and together with the enclosed form of proxy card, is first being mailed to Cantaloupe’s shareholders on or about [ ], 2025.

Dear Shareholder,

Notice is hereby given that a Special Meeting (which, including any adjournments or postponements thereof, we refer to as the “Special Meeting”) of the shareholders of Cantaloupe, Inc. (which we refer to as “Cantaloupe”) will be held on [ ], 2025, at [ ], Eastern time, virtually at www.virtualshareholdermeeting.com/CTLP2025SM.

We are holding the meeting for the following purposes:

Holders of record of our common stock, without par value (which we refer to as “common stock”) and Series A Convertible Preferred Stock, without par value (which we refer to as “preferred stock” and, together with common stock, “Cantaloupe stock”), outstanding as of the close of business on [ ], 2025 (which we refer to as the “record date”), are entitled to notice of, and to vote at, the Special Meeting or at any adjournment or postponement of the Special Meeting.

The Merger cannot be completed without the affirmative vote in favor of the approval of the Merger Proposal of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon, voting together as a single class. Approval of each of the Advisory Compensation Proposal and the Adjournment Proposal also requires the affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon, voting together as a single class. Approval of the Advisory Compensation Proposal and Adjournment Proposal are not conditions to the completion of the Merger. Each share of common stock outstanding as of the record date will be entitled to one vote on each matter submitted to our shareholders for approval at the Special Meeting. Each share of preferred stock outstanding as of the record date will be entitled to vote on an as-converted basis, with each share of preferred stock outstanding as of the record date entitling the holder thereof to 0.1988 of a vote on each matter submitted to our shareholders for approval at the Special Meeting (with any fractional vote determined on an aggregate conversion basis being rounded to the nearest whole number).

Our Board, after considering the factors more fully described in the accompanying proxy statement, unanimously (i) determined that the Merger Agreement and the transactions contemplated thereby, including the Merger, are in the best interests of Cantaloupe, (ii) approved, adopted and declared advisable the Merger Agreement and the transactions contemplated thereby, including the Merger, (iii) recommended the approval and adoption of the Merger Agreement by Cantaloupe’s shareholders and (iv) directed that the Merger Agreement be submitted to Cantaloupe’s shareholders for their vote to adopt the Merger Agreement at a duly convened meeting of Cantaloupe’s shareholders. Our Board recommends that shareholders vote “FOR” the Merger Proposal described in the accompanying proxy statement. Our Board further recommends that you vote “FOR” each of the Advisory Compensation Proposal and the Adjournment Proposal also described in the accompanying proxy statement.

Other sections of the accompanying proxy statement describe the proposals listed above in more detail, as well as other matters contemplated in connection with the Merger. Before voting, please carefully read the accompanying proxy statement in its entirety, including the Merger Agreement and all other annexes, and including documents incorporated by reference, for further information relevant to the business to be transacted at the Special Meeting. In particular, see the section of the accompanying proxy statement titled “The Merger Agreement”, which is incorporated into this notice by reference, for a description of the Merger Agreement and transactions contemplated thereby, including the Merger and the copy of the Merger Agreement which is included as Annex A to the accompanying proxy statement, which is incorporated into this notice by reference.

Your vote is important. Please vote by telephone, via the Internet, or by marking, signing and returning your proxy or voting instruction form as soon as possible, regardless of whether you plan to attend the Special Meeting.

The following questions and answers are intended to address some commonly asked questions regarding the Special Meeting and the Merger. These questions and answers may not address all questions that may be important to you as a holder of Cantaloupe stock. Please refer to the more detailed information contained elsewhere in this proxy statement, the annexes to this proxy statement and the documents referred to or incorporated by reference in this proxy statement.

Additionally, pursuant to the Merger Agreement, upon the terms and subject to the conditions set forth therein, Cantaloupe is required to redeem all of the outstanding shares of preferred stock immediately prior to the consummation of the Merger in accordance with the applicable redemption provisions contained in the Cantaloupe Articles, at a redemption price payable in cash, by or on behalf of Cantaloupe, in an amount equal to $11.00 per share of preferred stock plus an amount equal to the accrued and unpaid cumulative dividends thereon to the date of the Redemption. Five business days prior to the date of the closing of the Merger (or such other date as Cantaloupe and 365 agree), Cantaloupe will send the Redemption Notice to each record holder of such shares of preferred stock.

In accordance with the Cantaloupe Articles, holders of preferred stock may elect to convert each share of preferred stock (as well as any accrued and unpaid cumulative dividends thereon) into common stock, pursuant to and at the conversion price set forth in the Cantaloupe Articles, at any time prior to the date of the Redemption. Holders of preferred stock that convert their preferred stock into common stock will be entitled to receive $11.20 in cash, without interest and less any applicable withholding taxes, for each share of common stock into which the preferred stock converts, and will not receive the preferred stock redemption payment in respect of any shares of preferred stock that have been converted.

At or immediately prior to the effective time of the Merger, each Cantaloupe PSU that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe PSU, become vested with respect to that number of shares of common stock based on deemed achievement of the performance metrics at target performance. Immediately thereafter Cantaloupe PSUs will be canceled and converted into the right to receive, with respect to each such vested share of common stock underlying such Cantaloupe PSU, in accordance with the terms of the Merger Agreement, an amount in cash equal to the merger consideration.

At or immediately prior to the effective time of the Merger, each Cantaloupe Restricted Stock Award that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe Restricted Stock Award, become fully vested and free of restrictions and will be canceled and converted into the right to receive, in accordance with the terms of the Merger Agreement, an amount in cash equal to the merger consideration.

At or immediately prior to the effective time of the Merger, each In-the-Money Option that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe Option, become fully vested and free of restrictions and be canceled in exchange for cash in an amount equal to (i) the total number of shares of common stock for which such Cantaloupe Option is exercisable, multiplied by (ii) the excess of the merger consideration over the per share exercise price of such Cantaloupe Option. At the effective time of the Merger, each Out-of-the-Money Option that is outstanding immediately prior to the effective time of the Merger will be canceled without consideration and will be of no further force and effect.

The members of the Board have entered into Voting Agreements with 365 to vote in favor of the proposals set forth in this proxy statement. Although our executive officers, other than Mr. Venkatesan, are not obligated to vote to approve the Merger Agreement and the transactions contemplated thereby, we currently expect that each of our executive officers will vote all of their respective shares of common stock (1) “FOR” the Merger Proposal, (2) “FOR” the Advisory Compensation Proposal and (3) “FOR” the Adjournment Proposal.

Please see the section of this proxy statement titled “The Merger—Interests of Certain Persons in the Merger” for additional information about these financial interests.

Each share of common stock outstanding as of the record date will be entitled to one vote on each matter submitted to our shareholders for approval at the Special Meeting. Each share of preferred stock outstanding as of the record date will be entitled to vote on an as-converted basis, with each share of preferred stock outstanding as of the record date entitling the holder thereof to 0.1988 of a vote on each matter submitted to our shareholders for approval at the Special Meeting (with any fractional vote determined on an aggregate conversion basis being rounded to the nearest whole number).

As of the record date, holders of common stock in their capacity as such held approximately [ ]% of the outstanding voting power of our shareholders and holders of preferred stock in their capacity as such held approximately [ ]% of the outstanding voting power of our shareholders.

A list of our shareholders entitled to vote at the Special Meeting will be available during the Special Meeting at www.virtualshareholdermeeting.com/CTLP2025SM.

and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon, voting together as a single class. Each share of common stock outstanding as of the record date will be entitled to one vote on each matter submitted to our shareholders for approval at the Special Meeting. Each share of preferred stock outstanding as of the record date will be entitled to vote on an as-converted basis, with each share of preferred stock outstanding as of the record date entitling the holder thereof to 0.1988 of a vote on each matter submitted to our shareholders for approval at the Special Meeting (with any fractional vote determined on an aggregate conversion basis being rounded to the nearest whole number).

A broker non-vote or an abstention from voting for the Merger Proposal will not constitute or be counted as votes cast and, consequently, if a quorum is present at the Special Meeting, will have no effect on the outcome of the Merger Proposal.

Approval of the Advisory Compensation Proposal requires, assuming a quorum is present at the Special Meeting, the affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon, voting together as a single class. Approval of the Adjournment Proposal requires, whether or not a quorum is present at the Special Meeting, the affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon, voting together as a single class.

A broker non-vote or an abstention from voting for the Advisory Compensation Proposal or the Adjournment Proposal will not constitute or be counted as votes cast and, consequently, will have no effect on the outcome of the Advisory Compensation Proposal (assuming a quorum is present) or the Adjournment Proposal.

When a quorum is present to organize a meeting, it is not broken by the subsequent withdrawal of any shareholders. Abstentions are considered as present for the purpose of determining the presence of a quorum. Shares not in attendance and broker non-votes will not be counted towards the required quorum.

The Board recommends that Cantaloupe shareholders vote:

A:

If your shares are held through a nominee, you will receive separate voting instructions from your nominee. You must follow the voting instructions provided by your nominee in order to instruct your broker on how to vote your shares.

If you do not instruct your nominee to vote your shares, your shares will not be voted, and therefore will not constitute or be counted as votes cast.

If your shares are held through a nominee, you should contact your bank, broker or other nominee for instructions regarding how to change your vote.

through a broker or you may own shares through more than one broker. In these situations, you will receive multiple sets of proxy materials. You must complete, sign and return all of the proxy cards or follow the instructions for any alternative voting procedure on each of the voting instruction forms that you receive in order to vote all of the shares you own. Each proxy card you receive comes with its own prepaid return envelope; if you vote by mail, make sure you return each proxy card in the return envelope that accompanies that proxy card.

We expect to complete the Merger promptly following the receipt of the required Cantaloupe shareholder approval and all required regulatory approvals and the satisfaction or written waiver of the other conditions precedent described in the Merger Agreement.

You should consult your tax advisor for a complete analysis of the particular tax consequences of the Merger to you, including the applicability and effect of any U.S. federal, state and local and non-U.S. tax laws.

payment for their shares of common stock in connection with the Merger. Instead, Cantaloupe will remain an independent public company and our common stock will continue to be listed and traded on the Nasdaq. Additionally, if the Merger is not completed, we do not expect to redeem the shares of preferred stock as contemplated by the Merger Agreement.

In certain circumstances, we may be required to pay 365 a termination fee equal to $31.5 million in connection with a termination of the Merger Agreement as described under the section of this proxy statement titled “The Merger Agreement—Termination Fee; Effect of Termination”.

Sodali & Co.

430 Park Avenue, 14th Floor

New York, NY 10022

Shareholders may call toll-free: (800) 662-5200

Brokers, Banks, and Other Nominees may call collect: (203) 658-9400

Email: ctlp@info.sodali.com

If your nominee holds your shares, you should also call your nominee for additional information.

This proxy statement contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. We may also make written or oral forward-looking statements in our reports on Forms 10-K, 10-Q and 8-K, in press releases and other written materials and in oral statements made by our officers, directors or employees to third parties. Statements that are not historical facts, including statements about our beliefs and expectations, are forward-looking statements. Forward-looking statements are often characterized by the use of words such as “outlook”, “believes”, “estimates”, “expects”, “projects”, “may”, “intends”, “plans”, “anticipates”, “foresees”, “future” or by discussions of strategy, plans or intentions. The statements in this proxy statement that are not historical statements are forward-looking statements. Forward-looking statements involve many known and unknown risks, uncertainties, assumptions and other important factors that could cause actual conditions, actual results, performance or our achievements, or industry results, to differ materially from historical results, any future results or performance or achievements expressed or implied by such forward-looking statements. Certain risks and uncertainties include, but are not limited to, the following:

Important factors that could cause our actual results to differ materially from those expressed as forward-looking statements include, but are not limited to, the factors set forth in this proxy statement, in our latest Annual Report on Form 10-K for the fiscal year ended June 30, 2024, including but not limited to “Part I, Item 1A. Risk Factors” and “Part II, Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations” therein, in our Quarterly Report on Form 10-Q for the fiscal quarter ended September 30, 2024, including but not limited to “Part I, Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations” and “Part II, Item 1A. Risk Factors”, in our Quarterly Report on Form 10-Q for the fiscal quarter ended December 31, 2024, including but not limited to “Part I, Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations” and “Part II, Item 1A. Risk Factors”, in our Quarterly Report on Form 10-Q for the fiscal quarter ended March 31, 2025, including but not limited to “Part I, Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations” and “Part II, Item 1A. Risk Factors” and in our other filings with the SEC.

All forward-looking statements made herein are expressly qualified in their entirety by these cautionary statements and there can be no assurance that the actual results, events or developments referenced herein will occur or be realized. There may be other factors of which we are currently unaware or deem immaterial that may cause our actual results to differ materially from the forward-looking statements.

Forward-looking statements are based on current plans, estimates, assumptions and projections, and, therefore, you should not place undue reliance on them. Forward-looking statements speak only as of the date they are made, and except as required by law, we undertake no obligation to update them in light of new information or future events.

This proxy statement is being furnished to our shareholders as part of the solicitation of proxies by our Board for use at the Special Meeting to be held at on [ ], 2025, at [ ], Eastern time, or at any adjournment or postponement of such meeting. This proxy statement is first being mailed to our shareholders on or about [ ], 2025. Cantaloupe shareholders will be able to virtually attend and vote at the Special Meeting by visiting www.virtualshareholdermeeting.com/CTLP2025SM. Online check-in will start approximately 15 minutes before the Special Meeting is scheduled to begin.

If you are a shareholder of record, you may vote in any of the following ways:

If you intend to submit your proxy by mail, telephone or via the Internet, you must do so by 11:59 p.m., Eastern time, on [ ], 2025, the day before the Special Meeting. If your shares are held through a nominee, you will receive separate voting instructions from your nominee. You must follow the voting instructions provided by your nominee in order to instruct your broker on how to vote your shares.

We encourage you to vote by proxy by mail, telephone or over the Internet well in advance of the Special Meeting to ensure your shares are represented whether or not you decide to attend.

The purpose of the Special Meeting is for the holders of Cantaloupe stock to consider and vote upon the following proposals:

Shareholders must approve the proposal to approve and adopt the Merger Agreement in order for the Merger to occur. If our shareholders fail to approve the Merger Proposal, the Merger will not occur. A copy of the Merger Agreement is attached to this proxy statement as Annex A, which we encourage you to read carefully and in its entirety.

The holders of record of Cantaloupe stock as of the close of business on [ ], 2025 will be entitled to receive notice of and to vote at the Special Meeting. As of the record date, there were [ ] shares of our common stock outstanding and [ ] shares of our preferred stock outstanding.

The presence at the Special Meeting, virtually or represented by proxy, of shareholders entitled to cast at least a majority of the votes that all shareholders are entitled to cast on a particular matter at the Special Meeting will constitute a quorum at the Special Meeting.

If you have properly voted by proxy, via mail, telephone or the Internet, you will be considered part of the quorum. Proxies received but not marked or marked as abstentions will be included in the calculation of the number of shares considered to be present at the Special Meeting.

Each share of common stock outstanding as of the record date will be entitled to one vote on each matter submitted to our shareholders for approval at the Special Meeting. Each share of preferred stock outstanding as of the record date will be entitled to vote on an as-converted basis, with each share of preferred stock outstanding as of the record date entitling the holder thereof to 0.1988 of a vote on each matter submitted to our shareholders for approval at the Special Meeting (with any fractional vote determined on an aggregate conversion basis being rounded to the nearest whole number).

In accordance with the Nasdaq rules, banks, brokers and other nominees who hold shares of common stock in “street name” for their customers do not have discretionary authority to vote the shares with respect to any of the proposals to be voted on at the Special Meeting. Accordingly, if banks, brokers or other nominees do not receive specific voting instructions from the beneficial owner of such shares with respect to the proposals to be voted on at the Special Meeting, they may not vote such shares with respect to such proposals. Because all proposals for the Special Meeting are non-routine and non-discretionary, we do not expect there to be any broker non-votes for such proposals.

In the event that a quorum is not present at the Special Meeting, subject to the terms of the Merger Agreement, Cantaloupe expects to adjourn or postpone the Special Meeting until it solicits enough proxies to obtain a quorum. Pursuant to the Cantaloupe Bylaws, any meeting of Cantaloupe shareholders (including the Special Meeting) may be adjourned, whether or not a quorum is present, for such period and to such place as the shareholders present and entitled to vote will direct. However pursuant to the Merger Agreement, Cantaloupe may only adjourn or postpone the Special Meeting after consultation with 365, and if requested by 365 in writing, will adjourn or postpone the Special Meeting in compliance with applicable law (i) to the extent necessary to ensure that any supplement or amendment to the proxy statement that is required by applicable law is provided to Cantaloupe shareholders, (ii) if, as of the time for which the Special Meeting is scheduled as set forth in the proxy statement, there are an insufficient number of shares of Cantaloupe stock present or represented by proxy at the Special Meeting to constitute a quorum at such meeting, but only until there are a sufficient number of shares of Cantaloupe stock present or represented by proxy at the Special Meeting to obtain such a quorum or (iii) if as of the time for which the Special Meeting is scheduled as set forth in the proxy statement, there are insufficient shares of Cantaloupe stock represented (in person or by proxy) to obtain the required Cantaloupe shareholder approval, but only until there are a sufficient number of shares of common and preferred stock present or represented by proxy at the Special Meeting to obtain the required Cantaloupe shareholder approval; provided that the Special Meeting will not be adjourned or postponed pursuant to the foregoing clauses (ii) or (iii) to a date that is more than 15 days after the date on which the Special Meeting was originally scheduled without the prior written consent of 365 (which consent will not be unreasonably withheld, conditioned or delayed); provided further that with respect to an adjournment or postponement pursuant to the foregoing clauses (ii) or (iii), Cantaloupe will not change the record date for the Special Meeting without 365’s prior written consent (which consent will not be unreasonably withheld, conditioned or delayed) (it being understood and agreed, that if required by applicable law, Cantaloupe will be entitled to change the record date for the Special Meeting if such requirement by applicable law is unrelated to any adjournment or postponement pursuant to the foregoing clause (ii) or (iii)). Notwithstanding the foregoing, in the event that Cantaloupe postpones or adjourns the Special Meeting pursuant to the foregoing sentence, Cantaloupe will reconvene and hold the Special Meeting as promptly as reasonably practicable thereafter.

Each share of common stock outstanding as of the record date will be entitled to one vote on each matter submitted to our shareholders for approval at the Special Meeting. Each share of preferred stock outstanding as of the record date will be entitled to vote on an as-converted basis, with each share of preferred stock outstanding as of the record

date entitling the holder thereof to 0.1988 of a vote on each matter submitted to our shareholders for approval at the Special Meeting (with any fractional vote determined on an aggregate conversion basis being rounded to the nearest whole number).

Approval of the Merger Proposal requires, assuming a quorum is present at the Special Meeting, the affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon as of the record date, voting together as a single class.

Approval of the Advisory Compensation Proposal requires, assuming a quorum is present at the Special Meeting, the affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon as of the record date, voting together as a single class.

Approval of the Adjournment Proposal requires, whether or not a quorum is present at the Special Meeting, the affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon as of the record date, voting together as a single class.

A broker non-vote or an abstention from voting for the Merger Proposal will not constitute or be counted as votes cast and, consequently, if a quorum is present at the Special Meeting, will have no effect on the outcome of the Merger Proposal, the Advisory Compensation Proposal or the Adjournment Proposal.

Brokers, banks or other nominees holding shares of Cantaloupe stock in “street name” may not vote such shares of Cantaloupe stock on any of the proposals absent instruction from you on how you wish your shares of Cantaloupe stock to be voted. If your shares are held in “street name”, unless you virtually attend the Special Meeting with a properly executed legal proxy from your broker, bank or other nominee, your failure to provide instructions, if a quorum is present at the Special Meeting, will have no effect on the outcome of the Merger Proposal, the Advisory Compensation Proposal or the Adjournment Proposal.

If you vote by proxy, regardless of the method you choose to vote, the individuals named on the enclosed proxy card, and each of them, with full power of substitution, will vote your shares of Cantaloupe stock in the way that you indicate. When completing the telephone or Internet processes or the proxy card, you may specify whether your shares of Cantaloupe stock should be voted “FOR” or “AGAINST” or to “ABSTAIN” from voting on all, some or none of the specific items of business to come before the Special Meeting. If you sign, date and return your proxy card (or submit your proxy by telephone or the Internet) without indicating how you wish to vote on a proposal, your proxy will be voted in accordance with our Board’s recommendation—i.e., in favor of the Merger Proposal, the Advisory Compensation Proposal and the Adjournment Proposal. If you are a shareholder of record of Cantaloupe stock and fail to return your proxy card (or fail to submit your proxy by telephone or the Internet), unless you virtually attend the Special Meeting, the effect will be that your shares will not be counted for purposes of determining whether a quorum is present at the Special Meeting and, if a quorum is present at the Special Meeting, your shares will have no effect on the outcome of the vote on the Merger Proposal, the Advisory Compensation Proposal or the Adjournment Proposal.

If your shares of Cantaloupe stock are held in “street name”, you will receive instructions from your broker, bank, trust or other nominee that you must follow in order to have your shares voted. Your broker, bank, trust or other nominee will vote your shares only if you provide instructions on how to vote. Please follow the directions on the voting instruction form sent to you by your broker, bank, trust or other nominee with this proxy statement. If you have not received such voting instructions or require further information regarding such voting instructions, contact your broker, bank, trust or other nominee, as the case may be. Brokers who hold shares of Cantaloupe stock in “street name” for a beneficial owner of those shares typically have the authority to vote in their discretion on “routine” proposals when they have not received instructions from the beneficial owner. However, brokers are not allowed to exercise their voting discretion with respect to the approval of matters that are “non-routine”, such as the Merger Proposal, Adjournment Proposal and Advisory Compensation Proposal, without specific instructions from the beneficial owner. Because all proposals for the Special Meeting are non-routine and non-discretionary, we do not expect there to be any broker non-votes for such proposals.

If your shares are held in “street name”, unless you virtually attend the Special Meeting with a properly executed legal proxy from your broker, bank or other nominee, your failure to provide instructions will, assuming a quorum is present at the Special Meeting, have no effect on the outcome of the vote of the Merger Proposal, the Advisory Compensation Proposal or the Adjournment Proposal.

Any person giving a proxy pursuant to this solicitation has the power to revoke and change it any time before it is voted. If you are a shareholder of record of Cantaloupe stock, you may revoke your proxy by:

Attending the Special Meeting without taking one of the actions described above will not in itself revoke your proxy. Please note that if you want to revoke your proxy by mailing a new proxy card to Cantaloupe or by sending a written notice of revocation to Cantaloupe, you should ensure that you send your new proxy card or written notice of revocation in sufficient time for it to be received by Cantaloupe before the Special Meeting. If you intend to submit a new proxy by telephone or via the Internet, you must do so by 11:59 p.m., Eastern time, on [ ], 2025, the day before the Special Meeting.

If you hold your shares of Cantaloupe stock in “street name” through a nominee, you will need to follow the instructions provided to you by your nominee in order to revoke your voting instructions or submit new voting instructions.

Although it is not currently expected, subject to the terms of the Merger Agreement, the Special Meeting may be adjourned or postponed, including for the purpose of soliciting additional proxies. We are submitting a proposal for consideration at the Special Meeting to authorize the named proxies to approve one or more adjournments of the Special Meeting, if necessary or appropriate (as determined by the Board or the chairperson of the meeting) to solicit additional proxies in the event that there are insufficient votes at the time of the Special Meeting or any adjournment or postponement of the Special Meeting to establish a quorum or to approve and adopt the Merger Agreement or with 365’s prior written consent. Subject to the terms of the Merger Agreement, we retain full authority to the extent set forth in the Cantaloupe Bylaws and the PBCL to adjourn the Special Meeting (or any adjournment or postponement of the Special Meeting) or to postpone the Special Meeting (or any adjournment or postponement of the Special Meeting) without the consent of any shareholder.

If the Special Meeting is adjourned, we are not required to give notice of the time and place of the adjourned meeting if announced at the meeting at which the adjournment is taken, unless our Board fixes a new record date for the Special Meeting. Subject to the terms of the Merger Agreement, at any adjourned meeting, any business may be transacted which might have been transacted at the original meeting. All proxies will be voted in the same manner as they would have been voted at the original convening of the Special Meeting, except for any proxies that have been effectively revoked or withdrawn prior to the time the proxy is voted at the reconvened meeting.

Cantaloupe and 365 are working to complete the Merger in accordance with the terms of the Merger Agreement, and we expect it to be completed in the second half of calendar year 2025. If our shareholders vote to approve the Merger Proposal, the Merger will become effective as promptly as practicable following the satisfaction or written waiver of the other conditions to the Merger, subject to the terms of the Merger Agreement. See the section of this proxy statement titled “The Merger—Closing and Effective Time of the Merger”.

Under the PBCL, as well as the governing documents of Cantaloupe, holders of common stock are not entitled to dissenters rights in connection with the Merger. Upon the Redemption, the Merger will not entitle any former holder of preferred stock to any dissenters rights.

Our directors, officers and employees may solicit proxies by mail, by email, by telephone or in person. Those individuals will receive no additional compensation for solicitation activities. We have also engaged Sodali to assist in the solicitation of proxies and provide related advice and informational support. Under our agreement with Sodali, unless otherwise agreed by the parties, Sodali will receive a fee of $25,000, plus reimbursement of its reasonable, out-of-pocket expenses for its services and plus fees for calls (if any) to Cantaloupe shareholders. We will request banking institutions, brokerage firms, custodians, trustees, nominees and fiduciaries to forward solicitation materials to the beneficial owners of Cantaloupe stock held of record by those entities, and we will, upon request, reimburse reasonable forwarding expenses. We will pay the costs of preparing, printing, assembling and mailing the proxy materials used in the solicitation of proxies.

You should not return your stock certificate or send documents representing Cantaloupe stock with the proxy card. If the Merger is completed and your shares of Cantaloupe stock are held in book-entry through DTC or in “street name” by a broker or other nominee, Cantaloupe and 365 will cooperate to establish procedures to transmit the applicable cash proceeds. If the Merger is completed and you are a shareholder of record with your shares held in certificated form or held directly in your name in book-entry form other than through DTC, you will receive a letter of transmittal with instructions for returning such letter of transmittal, and, in the case of holders of share certificates, how to send your share certificates to the Paying Agent, in connection with the Merger. The Paying Agent will issue and deliver to you a check for your shares after you comply with these instructions.

If you have questions about the Merger or how to submit your proxy, or if you need additional copies of this proxy statement or the enclosed proxy card or voting instructions, please contact Sodali, our proxy solicitor, at:

Sodali & Co.

430 Park Avenue, 14th Floor

New York, NY 10022

Shareholders may call toll-free: (800) 662-5200

Brokers, Banks, and Other Nominees may call collect: (203) 658-9400

Email: ctlp@info.sodali.com

We are asking you to approve and adopt the Merger Agreement. If the Merger Agreement is approved and adopted by our shareholders and all other conditions to the closing of the Merger are either satisfied or validly waived, Merger Subsidiary will merge with and into Cantaloupe with Cantaloupe surviving the Merger as wholly owned subsidiary of Holdco II. Our common stock is currently traded on the Nasdaq under the symbol “CTLP”. If the Merger is completed, we will cease to be an independent public company and will become an indirect wholly owned subsidiary of 365. Following the completion of the Merger, the registration of our common stock and our reporting obligations under the Exchange Act will be terminated. In addition, upon the completion of the Merger, our common stock will no longer be listed on any stock exchange or quotation system, including the Nasdaq. Additionally, pursuant to the Merger Agreement, upon the terms and subject to the conditions set forth therein, Cantaloupe is required to redeem all of the outstanding shares of preferred stock immediately prior to the consummation of the Merger in accordance with the applicable redemption provisions contained in the Cantaloupe Articles, at a redemption price payable in cash, by or on behalf of Cantaloupe, in an amount equal to $11.00 per share of preferred stock plus an amount equal to the accrued and unpaid cumulative dividends thereon to the date of the Redemption.

For a summary of and detailed information regarding this proposal, see the information about the Merger Agreement and the Merger throughout this proxy statement, including the information set forth in the sections of this proxy statement titled “The Merger” and “The Merger Agreement”. A copy of the Merger Agreement is attached to this proxy statement as Annex A. You are urged to read the Merger Agreement carefully in its entirety.

We cannot complete the Merger without, assuming a quorum is present at the Special Meeting, the affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon, voting together as a single class. Each share of common stock outstanding as of the record date will be entitled to one vote on each matter submitted to our shareholders for approval at the Special Meeting. Each share of preferred stock outstanding as of the record date will be entitled to vote on an as-converted basis, with each share of preferred stock outstanding as of the record date entitling the holder thereof to 0.1988 of a vote on each matter submitted to our shareholders for approval at the Special Meeting (with any fractional vote determined on an aggregate conversion basis being rounded to the nearest whole number).

If you sign, date and return your proxy card (or submit your proxy by telephone or the Internet) without indicating how you wish to vote on a proposal, your proxy will be voted in accordance with our Board’s recommendation.

The Board unanimously recommends that shareholders vote “FOR” the Merger Proposal.

Set forth below is a detailed description of the Merger and the Merger Agreement.

This discussion of the Merger is qualified in its entirety by reference to the Merger Agreement, which is attached to this proxy statement as Annex A and incorporated into this proxy statement by reference. You should read the entire Merger Agreement carefully as it is the legal document that governs the Merger.

Cantaloupe, Inc. is a global technology leader powering self-service commerce. With over a million active locations, processing more than a billion transactions every year, Cantaloupe is enabling businesses of all sizes to provide self-service experiences for consumers. Cantaloupe’s vertically integrated solutions fuel growth by offering micro-payments processing, enterprise cloud software and IoT technology, as well as kiosk and POS innovations. Cantaloupe’s end-to-end platform increases consumer engagement and sales revenue through digital payments, consumer promotions and loyalty programs, while providing business owners increased profitability by leveraging software to drive efficiencies across an entire operation.

Cantaloupe is organized under the laws of the Commonwealth of Pennsylvania. The address and telephone number of its executive offices are 101 Lindenwood Drive, Suite 405, Malvern, Pennsylvania 19355, and (610) 989-0340.

Additional information about Cantaloupe is contained in its public filings, certain of which we incorporate by reference herein. See the section of this proxy statement titled “Where Shareholders Can Find More Information”.

Cantaloupe’s common stock is listed on the Nasdaq under the symbol “CTLP”.

365 is a leading innovator in unattended retail technology. Founded in 2008, 365 provides a full suite of best-in-class unattended technologies for food service operators including end-to-end integrated SaaS software, payment processing and POS hardware. Today, 365’s technology solutions autonomously power food retail spaces at corporate offices, manufacturing and distribution facilities, hospitality settings, senior living facilities, universities and more, in order to provide compelling foodservice options for consumers. 365’s technology solutions include a growing suite of frictionless smart stores, micro markets, vending, catering, and dining POS options to meet the expanding needs of its customers. 365 continuously pioneers innovation in the industry with superior technology, strategic partnerships and ultimate flexibility in customization and branding.

365 is organized under the laws of the State of Delaware. 365’s principal executive offices are located at 1743 Maplelawn Drive, Troy, Michigan 48084 and its telephone number is (888) 365-7382.

Holdco is a wholly owned subsidiary of 365, that was formed on June 12, 2025 for the sole purpose of entering into the Merger Agreement and completing the transactions contemplated by the Merger Agreement, including the Merger.

Holdco is organized under the laws of the state of Delaware. Holdco’s principal executive offices are located at 1743 Maplelawn Drive, Troy, Michigan 48084 and its telephone number is (888) 365-7382.

Holdco II is a wholly owned subsidiary of Holdco, that was formed on June 12, 2025 for the sole purpose of entering into the Merger Agreement and completing the transactions contemplated by the Merger Agreement, including the Merger.

Holdco II is organized under the laws of the state of Delaware. Holdco II’s principal executive offices are located at 1743 Maplelawn Drive, Troy, Michigan 48084 and its telephone number is (888) 365-7382.

Merger Subsidiary is a wholly owned subsidiary of Holdco II, that was formed on June 12, 2025 for the sole purpose of entering into the Merger Agreement and completing the transactions contemplated by the Merger Agreement, including the Merger. Upon the terms and subject to the conditions of the Merger Agreement, Merger Subsidiary will be merged with and into Cantaloupe, with Cantaloupe surviving the Merger as a wholly owned subsidiary of Holdco II.

Merger Subsidiary is organized under the laws of the state of Delaware. Merger Subsidiary’s principal executive offices are located at 1743 Maplelawn Drive, Troy, Michigan 48084 and its telephone number is (888) 365-7382.

As a result of the Merger, at the effective time of the Merger, each share of our common stock issued and outstanding immediately prior to the effective time of the Merger, but excluding the shares described in the following paragraph and the rollover shares (if any), will be converted into the right to receive $11.20 in cash, without interest and less any applicable withholding taxes.

At the effective time of the Merger, each share of Cantaloupe stock owned by Cantaloupe or any subsidiary of Cantaloupe as treasury stock (including all shares of preferred stock redeemed by Cantaloupe in accordance with the Merger Agreement) or owned by 365, Holdco, Holdco II or Merger Subsidiary, or by any other subsidiary of 365, immediately prior to the effective time of the Merger, will be canceled without payment.

Each rollover share (if any) will not be entitled to receive the merger consideration and will, (i) immediately prior to the effective time of the Merger, be subject to the treatment specified under the rollover agreement applicable to such rollover shares and (ii) at the effective time of the Merger, be canceled and retired and will cease to exist, and no consideration will be delivered in exchange for such cancellation and retirement. As of the date of this proxy statement, Douglas G. Bergeron, Chairman of the Board, has had preliminary discussions with representatives of 365 regarding a potential rollover arrangement with respect to shares of Cantaloupe’s common stock held by Mr. Bergeron, but, as of the date of this proxy statement, there is no understanding as to the amount of shares of Cantaloupe’s common stock that would be subject to such rollover arrangement, and no definitive agreement has been entered into between Mr. Bergeron and 365 or its affiliates regarding such potential rollover. Other than as described above, none of 365, Holdco, Holdco II, Merger Subsidiary or any of their respective affiliates has entered into any agreements, arrangements or understandings with respect to rollover shares.

At or prior to the effective time of the Merger, 365 must deposit, or cause to be deposited, with the Paying Agent, for the benefit of the holders of common stock, the Payment Fund.

The Cantaloupe Articles and the Cantaloupe Bylaws as in effect immediately prior to the effective time of the Merger will be the articles of incorporation and bylaws of the surviving corporation until thereafter amended as provided therein or in accordance with applicable law.

At the effective time of the Merger, the initial directors of Merger Subsidiary as of immediately prior to the effective time of the Merger will be the directors of the surviving corporation, each to hold office in accordance with the articles of incorporation and bylaws of the surviving corporation until their respective successors are duly elected or appointed and qualified.

At the effective time of the Merger, the initial officers of Merger Subsidiary as of immediately prior to the effective time of the Merger will be the officers of the surviving corporation, each to hold office in accordance with the articles of incorporation and bylaws of the surviving corporation until their respective successors are duly appointed.

If the Merger Agreement is not approved and adopted by our shareholders at the Special Meeting or if the Merger is not completed for any other reason, our shareholders will not receive the merger consideration or any payment for their shares of Cantaloupe stock in connection with the Merger. Instead, Cantaloupe will remain an independent public company and our common stock will continue to be listed and traded on the Nasdaq. In certain circumstances, we may be required to pay a termination fee in connection with a termination of the Merger Agreement. For more information about the circumstances in which Cantaloupe must pay 365 such termination fee, see the section of this proxy statement titled “The Merger Agreement—Termination Fee; Effect of Termination”. Additionally, if the Merger is not completed, Cantaloupe does not expect to redeem any shares of preferred stock.

Cantaloupe’s Board and executive management team regularly review Cantaloupe’s independent strategic plans, and consider various strategic alternatives potentially available to Cantaloupe, all with the goal of enhancing value for Cantaloupe and its shareholders. These reviews have included consideration, from time to time, of potential

partnerships, collaborations and other strategic transactions to enhance shareholder value, including potential sale transactions, consistent with shareholder requests over time. Cantaloupe’s executive management and the Board also engage in discussions from time to time with various industry participants, including strategic parties and financial sponsors, as well as financing sources, market participants and investment banking firms, regarding Cantaloupe’s business, strategy and growth opportunities, including opportunities for collaboration, potential business combinations, divestitures, acquisitions and financing transactions, and Cantaloupe’s executive management regularly updates the Board regarding the occurrence of such discussions.

As part of these discussions, Ravi Venkatesan, Cantaloupe’s Chief Executive Officer, has engaged in ordinary course conversations from time to time with various industry participants, including strategic parties and financial sponsors. Such conversations included separate meetings with representatives of two financial acquirors (which we refer to as “Party A” and “Party B”) and a strategic acquiror (which we refer to as “Party C”), at which meetings Mr. Venkatesan and such representatives discussed Cantaloupe and Cantaloupe’s industry generally. No terms of a potential transaction were discussed.

On December 4, 2024, representatives of a financial acquiror (which we refer to as “Party D”) contacted Mr. Venkatesan via email to request a telephonic meeting. Mr. Venkatesan and representatives of Party D met telephonically on December 10, 2024 and discussed Cantaloupe and Cantaloupe’s industry generally. No terms of a potential transaction were discussed.

On January 15, 2025, Mr. Venkatesan and representatives of Party D met in person and discussed Cantaloupe and Cantaloupe’s industry generally. No terms of a potential transaction were discussed.

On January 21, 2025, Party D sent Mr. Venkatesan a letter containing a preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $10.00 per share in cash (which we refer to as the “January 21 Party D Proposal”), which proposal represented a 22.7% premium to the closing price for shares of common stock of $8.15 on January 17, 2025, the last trading day prior to the January 21 Party D Proposal. The offer letter stated that the January 21 Party D Proposal was subject to a number of contingencies, including completing due diligence. Mr. Venkatesan promptly informed the Board of the January 21 Party D Proposal.

On January 24, 2025, the Board held a regularly scheduled meeting with members of Cantaloupe’s management present. At the meeting, the Board discussed, among other topics, the January 21 Party D Proposal. Mr. Venkatesan described to the Board his conversations with representatives of Party D prior to and following receipt of the January 21 Party D Proposal. Mr. Venkatesan also described to the Board the conversations he had with representatives of Party A, Party B and Party C. Mr. Venkatesan also reviewed with the Board Cantaloupe’s strategic framework, including its long-term strategy, financial performance expectations, operational priorities, market trends and key risks. During the same meeting, the Board discussed whether to engage a financial advisor to assist Cantaloupe’s management and the Board in evaluating Party D’s proposal, determining whether to explore a potential transaction and identifying other parties that might have interest in a potential transaction involving Cantaloupe should the Board determine that exploring a potential transaction was in the best interests of Cantaloupe.

Following discussion, the Board authorized Cantaloupe’s management to contact and, subject to review of information with respect to any potential conflicts of interest that J.P. Morgan may have with respect to a potential sale transaction, engage J.P. Morgan as Cantaloupe’s financial advisor. The Board based this determination on J.P. Morgan’s familiarity with Cantaloupe, J.P. Morgan’s extensive experience advising companies in the payments and financial services industries and J.P. Morgan’s significant experience providing strategic and financial advisory services. The Board also discussed certain strategic considerations in connection with a potential sale transaction, including the process and timing of a potential transaction and the parties that could have interest in acquiring Cantaloupe. After discussion, the Board authorized Cantaloupe’s management, with the assistance of J.P. Morgan, to conduct exploratory outreach to solicit interest from potential acquirors identified by J.P. Morgan and Cantaloupe’s management who could be interested in a transaction to acquire Cantaloupe.

On January 28, 2025, members of Cantaloupe’s management, including Mr. Venkatesan, met with representatives of J.P. Morgan to discuss, among other topics, the January 21 Party D Proposal and certain strategic considerations in connection with a potential sale transaction, as well as an overview of other potential acquirors of Cantaloupe. Following discussion, Cantaloupe’s management directed J.P. Morgan to inform Party D that J.P. Morgan would be acting as Cantaloupe’s financial advisor to evaluate the January 21 Party D Proposal. Cantaloupe’s management also reviewed with representatives of J.P. Morgan a number of potential strategic and financial acquirors that could be interested in a potential acquisition of Cantaloupe. Cantaloupe’s management discussed various potential acquirors

that J.P. Morgan had specifically identified and the reasons such potential acquirors may be interested in acquiring Cantaloupe, as well as additional potential acquirors that were not previously identified that could also be interested in a potential acquisition of Cantaloupe. After discussion, Cantaloupe’s management authorized J.P. Morgan to solicit interest from potential acquirors that had been discussed with Cantaloupe’s management to gauge their interest in a potential transaction with Cantaloupe.

Following the meeting on January 28, 2025 and at the direction of Cantaloupe’s management, representatives of J.P. Morgan discussed a potential transaction with 12 potential acquirors, including Party A, Party B, Party D and seven other potential financial acquirors (two of which we refer to as “Party E” and “Party F”) and Party C and one other potential strategic acquiror, to gauge their interest in a potential transaction with Cantaloupe.

On February 6, 2025, after the conclusion of trading hours, Cantaloupe reported the results of its fiscal quarter ended December 31, 2024. The closing price for shares of common stock on February 7, 2025, the first trading day following Cantaloupe’s earnings release, was $9.84, which represented a 13.5% increase to the closing price for shares of common stock of $8.67 on February 6, 2025.

On February 11, 2025, Party A verbally indicated to representatives of J.P. Morgan a preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for between $10.00 and $10.50 per share in cash (which we refer to as the “February 11 Party A Proposal”), which proposal, at $10.00 per share of common stock, represented a 0.7% premium to the closing price for shares of common stock of $9.93 on February 10, 2025, the last trading day prior to the February 11 Party A Proposal. Party A did not subsequently provide a written offer to the Board.

On February 22, 2025, a financial acquiror (which we refer to as “Party G”) sent Mr. Venkatesan a letter containing a preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $11.50 per share in cash (which we refer to as the “February 22 Party G Proposal”), which proposal represented a 9.0% premium to the closing price for shares of common stock of $10.55 on February 21, 2025, the last trading day prior to the February 22 Party G Proposal. The offer letter stated that the February 22 Party G Proposal was subject to a number of contingencies, including completing due diligence, and stated that the proposal assumed that key members of Cantaloupe’s management would remain in place after the consummation of the potential transaction.

On February 23, 2025, J.P. Morgan provided a relationship disclosure letter to the Board, which provided disclosures regarding J.P. Morgan and its affiliates’ commercial relationships with each of Cantaloupe, Party D and Hudson. On the same day, following review of J.P. Morgan’s relationship disclosure letter, Cantaloupe formally engaged J.P. Morgan as its financial advisor pursuant to an engagement letter dated as of February 23, 2025 reflecting this engagement.

On February 25, 2025, Reuters published an article stating that Cantaloupe was exploring strategic options, including a potential sale or a go-private transaction, and that it was working with investment bankers at J.P. Morgan in connection with such process. The closing price for shares of common stock on February 25, 2025 was $10.68, while the closing price for shares of common stock on February 24, 2025, the last trading day prior to the Reuters article, was $10.35 per share.

After the publication of the Reuters article, 12 additional potential acquirors contacted Cantaloupe’s management or representatives of J.P. Morgan to express interest in a potential acquisition of Cantaloupe, including 365 and 11 potential financial acquirors (one of which we refer to as “Party H”).

On March 2, 2025, the Board held a meeting with members of Cantaloupe’s management present. At the meeting, the Board discussed the process regarding a potential acquisition of Cantaloupe that was conducted to date, the feedback from potential acquirors, and the January 21 Party D Proposal, the February 11 Party A Proposal and the February 22 Party G Proposal. Also at the meeting, in order to facilitate the Board providing guidance to Cantaloupe’s management during the negotiations of the potential sale transaction, the Board formed a transaction committee (which we refer to as the “Transaction Committee”), consisting of Douglas Bergeron, Jacob Lamm, Michael Passilla, Mr. Venkatesan and Shannon Warren. The Board appointed these directors to the Transaction Committee based on their experience with respect to strategic transactions and their availability. The Board did not delegate any decision-making authority to the Transaction Committee. The Transaction Committee scheduled a meeting for the next day and invited J.P. Morgan to such meeting.

On March 3, 2025, the Transaction Committee held a meeting with members of Cantaloupe’s management and representatives of J.P. Morgan present. Representatives of J.P. Morgan reviewed the process regarding a potential

acquisition of Cantaloupe that was conducted to date, the feedback from potential acquirors and their preliminary views of each of the January 21 Party D Proposal, the February 11 Party A Proposal and the February 22 Party G Proposal. At the meeting, members of Cantaloupe’s management presented financial projections to the Transaction Committee. Representatives of J.P. Morgan discussed with the Transaction Committee J.P. Morgan’s preliminary financial perspective on Cantaloupe on a stand-alone basis. Representatives of J.P. Morgan also discussed with the Transaction Committee the recent stock price performance of Cantaloupe and other companies in the payments and financial services industries, premiums paid by acquirors in transactions involving U.S. publicly traded targets and potential next steps if Cantaloupe were to further evaluate the proposals. In addition, at the request of the Board, J.P. Morgan provided to the Board an additional relationship disclosure letter, which provided disclosures regarding J.P. Morgan and its affiliates’ commercial relationships with Party G.

Following discussion, the Transaction Committee directed Cantaloupe’s management, with the assistance of J.P. Morgan, to provide Party A, Party C, Party D and Party G with limited high-level information in order to enable these potential acquirors to continue their respective diligence processes. The Transaction Committee also directed Cantaloupe’s management, with the assistance of J.P. Morgan, to evaluate the potential acquirors that had contacted members of Cantaloupe’s management or representatives of J.P. Morgan following the publication of the Reuters article, and also to continue to solicit interest from additional potential financial and strategic acquirors to gauge their interest in a potential transaction with Cantaloupe.

Following the meeting on March 3, 2025, J.P. Morgan, at the direction of Cantaloupe’s management, contacted seven additional potential acquirors, including two potential financial acquirors and five potential strategic acquirors, to gauge their interest in a potential transaction with Cantaloupe.

By April 10, 2025, Cantaloupe had entered into confidentiality agreements with 11 potential acquirors, including 365, Party A, Party C, Party D, Party E, Party F, Party G, Party H and one other financial acquiror (which we refer to as “Party I”). None of these confidentiality agreements included “standstill” restrictions that would prevent a party from submitting an acquisition proposal following the execution of the Merger Agreement.

On March 12, 2025, Party E sent the Board a letter containing a preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for between $9.00 and $10.00 per share in cash (which we refer to as the “March 12 Party E Proposal”), which proposal, at $9.00 per share of common stock, represented a 11.1% premium to the closing price for shares of common stock of $8.10 on March 11, 2025, the last trading day prior to the March 12 Party E Proposal. The offer letter stated that the March 12 Party E Proposal was subject to a number of contingencies, including completing due diligence.

On March 17, 2025, Party F sent the Board a letter containing a preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $10.00 per share in cash (which we refer to as the “March 17 Party F Proposal”), which proposal represented a 29.7% premium to the closing price for shares of common stock of $7.71 on March 14, 2025, the last trading day prior to the March 17 Party F Proposal. The offer letter stated that the March 17 Party F Proposal was subject to a number of contingencies, including completing due diligence.

On March 24, 2025, the Transaction Committee held a meeting with members of Cantaloupe’s management and representatives of J.P. Morgan present to discuss, among other topics, the January 21 Party D Proposal, the February 11 Party A Proposal, the February 22 Party G Proposal, the March 12 Party E Proposal and the March 17 Party F Proposal. Representatives of J.P. Morgan updated the Transaction Committee on the offers received from potential acquirors and the transaction process to date, as well as the diligence topics on which potential acquirors had been focused. Following discussion, the Transaction Committee directed J.P. Morgan to solicit from Party A, Party D, Party E, Party F and Party G updated offers, to be submitted by April 18, 2025 following additional diligence by such potential acquirors of Cantaloupe, and to continue to solicit interest from additional potential financial and strategic acquirors.

On March 29, 2025, 365 sent the Board a letter containing a preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $10.50 per share in cash (which we refer to as the “March 29 365 Proposal”), which proposal represented a 38.7% premium to the closing price for shares of common stock of $7.57 on March 28, 2025, the last trading day prior to the March 29 365 Proposal. The offer letter stated that the March 29 365 Proposal was subject to a number of contingencies, including completing due diligence.

On March 31, 2025, the Transaction Committee held a meeting with members of Cantaloupe’s management and representatives of J.P. Morgan present. Representatives of J.P. Morgan updated the Transaction Committee on the

March 29 365 Proposal and the transaction process to date. Following discussion, the Transaction Committee directed J.P. Morgan to solicit from 365 an updated offer, to be submitted by April 18, 2025 following additional diligence by 365, and to continue to solicit interest from additional potential financial and strategic acquirors.

On April 6, 2025, Party H sent the Board a letter containing a preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $11.00 per share in cash (which we refer to as the “April 6 Party H Proposal”), which proposal represented a 47.3% premium to the closing price for shares of common stock of $7.47 on April 4, 2025, the last trading day prior to the April 6 Party H Proposal. The offer letter stated that the April 6 Party H Proposal was subject to a number of contingencies, including completing due diligence.

On April 7, 2025, Party D sent the Board a letter containing a revised preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $10.00 per share in cash (which we refer to as the “April 7 Party D Proposal”), which proposal represented a 33.9% premium to the closing price for shares of common stock of $7.47 on April 4, 2025, the last trading day prior to the April 7 Party D Proposal. The April 7 Party D Proposal of $10.00 per share was equivalent to the per share price included in the January 21 Party D Proposal. The offer letter stated that the April 7 Party D Proposal was subject to a number of contingencies, including completing due diligence.

On April 15, 2025, Party B and Party I jointly sent the Board a letter containing a preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $10.00 per share in cash (which we refer to as the “April 15 Party B Proposal”), which proposal represented a 30.5% premium to the closing price for shares of common stock of $7.66 on April 14, 2025, the last trading day prior to the April 15 Party B Proposal. The offer letter stated that the April 15 Party B Proposal was subject to a number of contingencies, including completing due diligence. The April 15 Party B Proposal also contemplated that certain, unspecified existing shareholders would roll their equity in Cantaloupe into the post-closing company.

On April 21, 2025, Party C sent the Board a letter containing a preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $10.00 per share, with 80% of the consideration to be cash and 20% to be Party C’s stock (which we refer to as the “April 21 Party C Proposal”), which proposal represented a 32.8% premium to the closing price for shares of common stock of $7.53 on April 17, 2025, the last trading day prior to the April 21 Party C Proposal. The offer letter stated that the April 21 Party C Proposal was subject to a number of contingencies, including completing due diligence.

On April 22, 2025, 365 sent the Board a letter containing a revised preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $10.75 per share in cash (which we refer to as the “April 22 365 Proposal”), which proposal represented a 45.5% premium to the closing price for shares of common stock of $7.39 on April 21, 2025, the last trading day prior to the April 22 365 Proposal. The April 22 365 Proposal of $10.75 per share represented an increase of $0.25 per share relative to the per share price included in the March 29 365 Proposal. The offer letter stated that the April 22 365 Proposal was subject to a number of contingencies, including completing due diligence.

On April 23, 2025, Party F sent the Board a letter containing a revised preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $9.20 per share in cash (which we refer to as the “April 23 Party F Proposal”), which proposal represented a 21.1% premium to the closing price for shares of common stock of $7.60 on April 22, 2025, the last trading day prior to the April 23 Party F Proposal. The April 23 Party F Proposal of $9.20 per share represented a decrease of $0.80 per share relative to the per share price included in the March 17 Party F Proposal. The offer letter stated that the April 23 Party F Proposal was subject to a number of contingencies, including completing due diligence.

On April 24, 2025, the Transaction Committee held a meeting with members of Cantaloupe’s management and representatives of J.P. Morgan present to discuss, among other topics, the non-binding proposals received from 365, Party C, Party D, Party E, Party F, Party G, Party H and Party B and Party I. Mr. Venkatesan and other members of Cantaloupe’s management described to the Transaction Committee their interactions with representatives of the potential acquirors and the diligence processes to date. Representatives of J.P. Morgan provided the Transaction Committee with an update on the M&A market in North America, the deal process and the non-binding proposals received from potential acquirors of Cantaloupe, and also discussed with the Transaction Committee J.P. Morgan’s preliminary financial perspective on Cantaloupe on a stand-alone basis. Representatives of J.P. Morgan recommended to the Transaction Committee that a limited number of potential acquirors be permitted to conduct full due diligence, including being granted access to additional information in a virtual data room, in order to advance their respective diligence processes and potentially increase their respective offer prices. Also at the meeting, Cantaloupe’s

management and representatives of J.P. Morgan discussed with the Transaction Committee the possible interest that other third parties may have in evaluating a potential transaction with Cantaloupe. Following discussion, the Transaction Committee determined that the outreach to potential acquirors already conducted by Cantaloupe’s management and representatives of J.P. Morgan, in addition to the Reuters report in February 2025 indicating that Cantaloupe was exploring strategic options, meant that it was unlikely another third party would be willing to pay more than the potential acquirors that had already submitted non-binding proposals. The Transaction Committee then discussed which potential acquirors would be granted full diligence access. After discussion with representatives of J.P. Morgan and Cantaloupe’s management, the Transaction Committee determined to recommend to the Board that 365, Party C, Party D and Party H be granted full diligence access, based on the previously submitted non-binding proposals and the Transaction Committee’s belief that these potential acquirors had the financial capacity to increase the price of their respective offers, as well as the transaction experience and sophistication to successfully complete a potential strategic transaction with Cantaloupe. The Transaction Committee also decided to invite King & Spalding LLP (which we refer to as “King & Spalding”), outside counsel to Cantaloupe, to the Board meeting to be held on May 1, 2025.

On May 1, 2025, the Board held a meeting with members of Cantaloupe’s management and representatives of King & Spalding and J.P. Morgan present. At the meeting, representatives of King & Spalding discussed with the members of the Board their fiduciary duties, both in general and in the context of various types of strategic transactions, as well as how the Board might evaluate a potential transaction with the potential acquirors of Cantaloupe. Also at the meeting, members of Cantaloupe’s management reviewed the financial projections (as described below in the section of this proxy statement titled “The Merger—Management Projections”) with the Board that had been presented at the Transaction Committee’s March 3, 2025 meeting. Representatives of J.P. Morgan also provided the Board with an update on the M&A market in North America, the deal process and the non-binding proposals received from potential acquirors of Cantaloupe, and also discussed with the Board J.P. Morgan’s preliminary financial perspective on Cantaloupe on a stand-alone basis. Also at the meeting, members of Cantaloupe’s management and representatives of J.P. Morgan described the potential sale transaction process to date, including an overview of the non-binding proposals received from 365, Party A, Party D, Party E, Party F, Party G and Party H, and described to the Board that the Transaction Committee had recommended providing full diligence access to 365, Party C, Party D and Party H and to continue discussions regarding a potential strategic transaction with these four potential acquirors of Cantaloupe. The Board discussed the Transaction Committee’s recommendations with members of the Transaction Committee and representatives of J.P. Morgan, including discussion of the possible interest that other third parties may have in evaluating a potential transaction with Cantaloupe. Following discussion, the Board agreed with the Transaction Committee’s determination that the outreach to potential acquirors already conducted by Cantaloupe’s management and representatives of J.P. Morgan, in addition to the Reuters report in February 2025 indicating that Cantaloupe was exploring strategic options, meant that it was unlikely another third party would be willing to pay more than the potential acquirors that had already submitted non-binding proposals. Following discussion, including the Board’s weighing of the prospects of achieving long-term value for Cantaloupe’s shareholders through execution of Cantaloupe’s strategic business plan against the value to shareholders that could be realized through a potential sale transaction at a significant premium to the recent and historical market prices of Cantaloupe’s common stock and certain other factors more fully described below under the heading “The Merger—Recommendation of the Board and Reasons for the Merger”, the Board determined that it would be in the best interests of Cantaloupe to further explore a potential sale transaction. The Board then directed Cantaloupe’s management, with the assistance of J.P. Morgan, to provide full diligence access to 365, Party C, Party D and Party H and to continue discussions regarding a potential strategic transaction with these four potential acquirors of Cantaloupe.

During the weeks following the May 1, 2025 Board meeting, members of Cantaloupe’s management, with the assistance of J.P. Morgan, provided additional diligence information to 365, Party C, Party D and Party H.

On May 12, 2025, representatives of Party H informed representatives of J.P. Morgan that Party H would no longer be participating in the process to potentially acquire Cantaloupe.

As part of the diligence process, members of Cantaloupe’s management, including Mr. Venkatesan and Scott Stewart, Cantaloupe’s Chief Financial Officer, held full-day meetings with representatives of 365 and Providence Equity Partners L.L.C. (which we refer to as “Providence”) on May 14, 2025, with representatives of Party D on May 21, 2025 and with representatives of Party C on May 22, 2025, in each case to provide additional information on

Cantaloupe and to answer questions from the representatives of the potential acquirors of Cantaloupe. Members of Cantaloupe’s management also met with representatives of 365’s outside counsel, Weil, Gotshal & Manges LLP (which we refer to as “Weil”), Party C’s outside counsel and Party D’s outside counsel to discuss certain legal due diligence matters.

On May 15, 2025, the Transaction Committee held a meeting with members of Cantaloupe’s management and representatives of King & Spalding and J.P. Morgan present to discuss, among other topics, the status of the respective diligence processes of 365, Party C and Party D, the timeline for the transaction process and the merger agreement that was to be provided to potential acquirors of Cantaloupe. Mr. Venkatesan described to the Transaction Committee the meeting between members of Cantaloupe’s management and representatives of 365 and Providence. Representatives of King & Spalding then reviewed the key terms of the draft of the merger agreement that would be distributed to potential acquirors of Cantaloupe, including a termination fee of 2.5% of Cantaloupe’s equity value payable by Cantaloupe in certain circumstances if Cantaloupe were to terminate the merger agreement to accept a “superior proposal” from a third party (which we refer to as a “company termination fee”). After discussion, the Transaction Committee directed representatives of J.P. Morgan to provide the draft of the merger agreement to 365, Party C and Party D. Members of the Transaction Committee and representatives of J.P. Morgan discussed when to ask 365, Party C and Party D for their “best and final” offers to acquire Cantaloupe. After discussion, the Transaction Committee decided to wait until the following week before determining the deadline for “best and final” offers, in order to permit the potential acquirors to further progress their respective diligence efforts.

On May 23, 2025, Party B and Party I jointly sent the Board a letter containing a revised preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $10.50 per share in cash (which we refer to as the “May 23 Party B Proposal”), which proposal represented a 19.5% premium to the closing price for shares of common stock of $8.79 on May 22, 2025, the last trading day prior to the May 23 Party B Proposal. The May 23 Party B Proposal of $10.50 per share represented an increase of $0.50 per share relative to the per share price included in the April 15 Party B Proposal.

On May 27, 2025, after consultation with and at the direction of Cantaloupe’s management, representatives of J.P. Morgan contacted representatives of 365, Party C, Party D and Party B and Party I to solicit “best and final” offers, which representatives of J.P. Morgan indicated should be submitted by 12:00 p.m., Eastern time, on June 10, 2025. Concurrently with requesting the “best and final” offers and at the direction of Cantaloupe’s management, representatives of J.P. Morgan also sent to representatives of 365, Party C, Party D and Party B and Party I the initial draft of the merger agreement. The initial draft of the merger agreement included, among other things, consideration payable to Cantaloupe’s shareholders in the form of cash and a company termination fee of 2.5% of equity value. At the direction of Cantaloupe’s management, representatives of J.P. Morgan instructed the potential acquirors of Cantaloupe to submit an issues list in respect of the merger agreement by 12:00 p.m., Eastern time, on June 3, 2025 and further instructed each potential acquiror of Cantaloupe that its bid on June 10, 2025 should be accompanied by a revised draft of the merger agreement in a form that such potential acquiror would be willing to execute.

On May 28, 2025, Cantaloupe entered into a confidentiality agreement with Party B, which confidentiality agreement did not include “standstill” restrictions that would prevent such party from submitting an acquisition proposal following the execution of the Merger Agreement. Following execution of the confidentiality agreement, Party B and Party I were permitted to conduct additional diligence.

On June 1, 2025, representatives of Weil sent representatives of King & Spalding an issues list pertaining to the draft merger agreement, which issues list proposed, among other things, a company termination fee of 4.0% of Cantaloupe’s enterprise value and that 365 would require Hudson and the nine directors and officers of Cantaloupe holding the greatest ownership of Cantaloupe’s common stock to enter into voting agreements. The issues list also indicated that 365’s position on the “end date” under the merger agreement was subject to discussion between representatives of King & Spalding and Weil. Representatives of King & Spalding met with representatives of Weil on June 3, 2025 to discuss the issues list.

Later on June 2, 2025, Street Insider published a report online indicating that multiple parties were involved in process to potentially acquire Cantaloupe. The closing price for shares of common stock on May 30, 2025, the last trading day prior to the Street Insider report, was $8.37 per share (which we refer to as the “unaffected stock price”).

On June 3, 2025, representatives of Party D’s outside counsel sent representatives of King & Spalding a revised draft merger agreement and an issues list pertaining to the draft merger agreement. Party D’s revised draft of the merger agreement included, among other things, a company termination fee of 4.0% of Cantaloupe’s equity value. Party D

also indicated that Hudson and each member of the Board would be required to enter into voting agreements, and Party D provided a draft voting agreement. Party D also indicated in its issues list that Party D was open to equity rollovers with certain shareholders, which Party D would be willing to discuss at the appropriate times and with the permission of the Board. Representatives of King & Spalding met with representatives of Party D’s outside counsel on June 4, 2025 to discuss Party D’s revised draft merger agreement.

On June 4, 2025, representatives of Party C’s outside counsel sent representatives of King & Spalding an issues list pertaining to the draft merger agreement, which issues list proposed, among other things, that consideration for the merger would be composed of a mix of cash and Party C’s stock and a company termination fee of 4.5% of Cantaloupe’s equity value. Party C also indicated that Hudson and each member of the Board would be required to enter into voting agreements.

On June 5, 2025, representatives of Weil sent representatives of King & Spalding a revised draft merger agreement. As had been discussed between representatives of King & Spalding and Weil on June 3, 2025, 365’s revised draft of the merger agreement included, among other things, a company termination fee of 4.0% of Cantaloupe’s enterprise value and an “end date” in the merger agreement of 12 months, with no contemplated extension.

On June 6, 2025, representatives of King & Spalding separately discussed with representatives of Weil and representatives of Party D’s outside counsel the terms of the merger agreement, including the company termination fee.

On June 7, 2025, representatives of King & Spalding sent revised merger agreements to representatives of Weil and representatives of Party D’s outside counsel. The draft merger agreements included, among other things, a proposed company termination fee of 3.0% of Cantaloupe’s enterprise value (in the case of the draft merger agreement sent to representatives of Weil) and 3.0% of Cantaloupe’s equity value (in the case of the draft merger agreement sent to representatives of Party D’s outside counsel).

On June 9, 2025, representatives of King & Spalding separately discussed with representatives of Weil and representatives of Party D’s outside counsel the terms of the merger agreement, including the company termination fee.

Later on June 9, 2025, representatives of Party D sent representatives of King & Spalding a revised draft of the merger agreement. The draft merger agreement included, among other things, a proposed company termination fee of 4.0% of Cantaloupe’s equity value and contemplated that Party D would provide an equity commitment letter in respect of the entire purchase price for the transaction, and that Party D would not require debt financing.

In the morning of June 10, 2025, 365 delivered a revised proposal to acquire 100% of Cantaloupe’s common stock for $10.75 per share in cash (which we refer to as the “June 10 365 Proposal”), which proposal represented a 28.4% premium to the unaffected stock price. The June 10 365 Proposal of $10.75 per share was equivalent to the per share price included in the April 22 365 Proposal. The offer letter stated that 365 had completed its due diligence and that it desired to move quickly to finalize and sign definitive documentation. The offer letter also stated that once 365 received approval from the Board, 365 intended to discuss the go-forward role and compensation package with each member of Cantaloupe’s senior executive team. 365 also submitted a revised draft of the merger agreement, a draft voting agreement and an executed debt commitment letter. The merger agreement provided by 365 included, among other things, a proposed company termination fee of 3.85% of Cantaloupe’s enterprise value and an “end date” in the merger agreement of 12 months, with no contemplated extension.

Later that day, Party B and Party I jointly delivered a revised preliminary non-binding proposal to acquire 100% of Cantaloupe’s common stock for $10.50 per share in cash (which we refer to as the “June 10 Party B Proposal”), which proposal represented a 25.4% premium to the unaffected stock price. The June 10 Party B Proposal of $10.50 per share was equivalent to the per share price included in the May 23 Party B Proposal. The offer letter submitted by Party B and Party I indicated that such parties were interested in continuing to explore a potential transaction, but did not contain any proposed terms of the transaction other than price, and Party B and Party I did not submit debt or equity commitment letters or a revised draft of the merger agreement.

Later that same day, Party D delivered a revised proposal to acquire 100% of Cantaloupe’s common stock for $10.00 per share in cash (which we refer to as the “June 10 Party D Proposal”), which proposal represented a 19.5% premium to the unaffected stock price. The June 10 Party D Proposal of $10.00 per share was equivalent to the per share price included in the April 7 Party D Proposal. The offer letter stated that Party D had substantially

completed its due diligence and that Party D believed it could be in a position to sign definitive documentation within two days. The offer letter also indicated that Party D would consider equity rollovers with certain shareholders and would discuss such rollovers after receiving permission from the Board.

Later that same day, Party C delivered a revised proposal to acquire 100% of Cantaloupe’s common stock for $10.00 per share, with 73% of the consideration to be cash and 27% to be Party C’s stock (which we refer to as the “June 10 Party C Proposal”), which proposal represented a 19.5% premium to the unaffected stock price. The June 10 Party C Proposal of $10.00 per share was equivalent to the per share price included in the April 21 Party C Proposal. The offer letter included a schedule of diligence items required by Party C before Party C would be in a position to execute definitive documentation, and Party C requested that Cantaloupe enter into an exclusivity agreement providing for exclusive negotiations for 15 business days. Party C also submitted a revised draft of the merger agreement and a draft, unexecuted debt commitment letter. The draft merger agreement provided by Party C included, among other things, a proposed company termination fee of 4.5% of Cantaloupe’s equity value.

During the morning of June 11, 2025, the Transaction Committee held a meeting with members of Cantaloupe’s management and representatives of King & Spalding and J.P. Morgan present. Representatives of J.P. Morgan updated the Transaction Committee on the offers received from potential acquirors and the transaction process to date, including that Cantaloupe’s management and representatives of J.P. Morgan had discussed a sale of Cantaloupe with 36 potential acquirors, of which 27 were financial acquirors and nine were strategic acquirors. Cantaloupe’s management and representatives of J.P. Morgan then provided their preliminary view of the offers received from 365, Party C, Party D and Party B and Party I on June 10. Cantaloupe’s management and representatives of J.P. Morgan described to the Transaction Committee that the June 10 365 Proposal and the June 10 Party D Proposal had no material contingencies, while the June 10 Party C Proposal and the June 10 Party B Proposal had material contingencies and would require more time before Party C or Party B and Party I was prepared to sign definitive documentation, including, in the case of Party B and Party I, time required for Party B and Party I to obtain financing for a potential transaction.

Next, representatives of King & Spalding reviewed the draft merger agreements submitted by 365, Party D and Party C with their respective proposals. Representatives of King & Spalding compared the terms of the draft merger agreements submitted by 365, Party C and Party D, including terms related to the financing, remedies of the parties and certain regulatory matters, and how such terms of the merger agreements affected the timing and certainty of closing. Representatives of King & Spalding advised the Transaction Committee that the draft merger agreement with Party D had no material outstanding issues and that representatives of King & Spalding could quickly finalize the terms of the merger agreement with representatives of Party D’s outside counsel. Representatives of King & Spalding then advised the Transaction Committee that the draft merger agreement with 365 had limited material outstanding issues, including the length of the “end date” in the merger agreement after which the merger agreement could be terminated by either party if the transaction had not closed. Representatives of King & Spalding also advised the Transaction Committee that the draft merger agreement with Party C had many outstanding material issues, including related to the fact that Party C was offering, in part, consideration in the form of Party C’s stock.

Following discussion, the Transaction Committee determined that the June 10 365 Proposal and the June 10 Party D Proposal provided Cantaloupe with the most certainty of execution and closing, taking into account each such potential acquiror’s progress in the diligence and negotiation processes to date and timeline to execution of a definitive agreement, as compared to the less certain June 10 Party B Proposal and June 10 Party C Proposal. The Transaction Committee then discussed with Cantaloupe’s management and representatives of J.P. Morgan and King & Spalding the potential for Cantaloupe to obtain increased offers from 365 and Party D. Following such discussion, the Transaction Committee directed J.P. Morgan to seek revised offers from each of 365 and Party D. The Transaction Committee also authorized Cantaloupe’s management to obtain additional information from 365 and Party D regarding the general terms of post-closing employment that those parties would be willing to provide to Cantaloupe’s employees, including Cantaloupe’s executive officers. As part of this authorization, Cantaloupe’s management was instructed by representatives of King & Spalding not to discuss the pricing terms of any revised offer with 365 and Party D. The Transaction Committee also directed representatives of King & Spalding to contact representatives of Weil to seek improved merger agreement terms, including with respect to an extension of the “end date” in the merger agreement.

Following the Transaction Committee meeting on June 11, 2025, representatives of J.P. Morgan contacted representatives of 365 and Party D, instructing each of 365 and Party D to submit a revised offer by the end of the day on June 12, 2025.

Later on June 11, 2025, representatives of King & Spalding sent representatives of Weil a revised draft of the merger agreement, which included, among other things, a company termination fee of $30.0 million (approximately 3.7% of equity value, based on the June 10 365 Proposal) and a longer “end date” in the merger agreement.

Later that same day, Party D delivered a final, revised proposal to acquire 100% of Cantaloupe’s common stock for $10.50 per share in cash (which we refer to as the “June 11 Party D Proposal”), which proposal represented a 25.4% premium to the unaffected stock price. The June 11 Party D Proposal of $10.50 per share represented an increase of $0.50 per share relative to the per share price included in the June 10 Party D Proposal.

On June 12, 2025, 365 delivered a final, revised proposal to acquire 100% of Cantaloupe’s common stock for $11.20 per share in cash (which we refer to as the “June 12 365 Proposal”), which proposal represented a 33.8% premium to the unaffected stock price. The June 12 365 Proposal of $11.20 per share represented an increase of $0.45 per share relative to the per share price included in the June 10 365 Proposal. The June 12 365 Proposal indicated that 365 would permit management and directors of Cantaloupe to roll over any portion of their equity, but that the June 12 365 Proposal was not conditioned upon any level of rollover, and that 365 planned for a majority of Cantaloupe’s senior management to have a meaningful go-forward role with the 365 following the closing of the proposed transaction.

Later on June 12, 2025, representatives of King & Spalding discussed with representatives of Weil the terms of the merger agreement. Representatives of Weil described certain terms of the merger agreement that 365 would be willing to accept, including a company termination fee of $31.5 million (approximately 3.7% of equity value, based on the June 12 365 Proposal). Representatives of King & Spalding and Weil also discussed the length of an extension to the “end date” of the merger agreement. Consistent with the June 12 365 Proposal, representatives of Weil also indicated that 365 would permit management and directors of Cantaloupe to roll over any portion of their equity, but that discussions related to any rollovers would not occur until after execution of a definitive merger agreement.

During the evening on June 12, 2025, the Transaction Committee held a meeting with members of Cantaloupe’s management and representatives of King & Spalding and J.P. Morgan present. At the meeting, representatives of J.P. Morgan provided their preliminary view of the June 11 Party D Proposal and the June 12 365 Proposal. Representatives of J.P. Morgan also described to the Transaction Committee the discussions they had with representatives of 365 and Party D following the Transaction Committee meeting on June 11, 2025, including their view that the revised offers from 365 and Party D represented their respective “best and final” offers. Representatives of King & Spalding then apprised the Transaction Committee of its conversations with representatives of Weil, including 365’s positions on the company termination fee and on the “end date” of the merger agreement. Representatives of King & Spalding informed the Transaction Committee that there were no other material outstanding issues in the merger agreement and that representatives of King & Spalding could quickly finalize the terms of the merger agreement with representatives of Weil. Following discussion, the Transaction Committee directed Cantaloupe’s management, with the assistance of King & Spalding, to finalize the definitive merger agreement with 365 at a price per share of $11.20 and on the contractual terms that had been discussed earlier that day between representatives of King & Spalding and Weil.

Later on June 12, 2025, representatives of Weil sent representatives of King & Spalding a revised draft of the merger agreement that reflected the terms discussed earlier that day, including a company termination fee of $31.5 million (approximately 3.7% of equity value, based on the June 12 365 Proposal), which terms the Transaction Committee had indicated its support for at its meeting earlier that day.

During the afternoon on June 13, 2025, the Board held a meeting with members of Cantaloupe’s management and representatives of King & Spalding and J.P. Morgan present. Prior to the meeting, the Board received certain preliminary materials prepared by representatives of King & Spalding and J.P. Morgan. In addition, J.P. Morgan provided to the Board an updated relationship disclosure letter which provided disclosures regarding J.P. Morgan and its affiliates’ commercial relationships with each of Cantaloupe, 365, Providence, Party D and Hudson. At the meeting, representatives of King & Spalding reviewed with the Board the key terms of the draft merger agreement with 365 and other transaction documents that had been negotiated with representatives of 365. In addition, representatives of King & Spalding reviewed with the Board, including the members of the Compensation Committee of the Board, certain compensation matters related to the merger agreement, including the treatment of Cantaloupe’s equity awards in the transaction. Representatives of J.P. Morgan described to the Board the transaction process that resulted in the June 12 365 Proposal, including that Cantaloupe’s management and representatives of J.P. Morgan had discussed a potential sale of Cantaloupe with 36 potential acquirors, of which 27 were financial acquirors and nine

were strategic acquirors. Representatives of J.P. Morgan then reviewed J.P. Morgan’s preliminary views of the merger consideration of $11.20 per share of common stock. Following such discussion, the Board directed Cantaloupe’s management, with the assistance of King & Spalding, to finalize the transaction documents on the contractual terms included in the June 12 365 Proposal and the subsequent discussions between representatives of King & Spalding and Weil, including a price per share of $11.20, and authorized Cantaloupe’s management to discuss certain employee retention, compensation and benefits-related matters with 365.

After the Board meeting on June 13, 2025 and through June 15, 2025, representatives of Cantaloupe, 365, King & Spalding and Weil discussed and finalized the transaction documents. Representatives of Cantaloupe, 365, King & Spalding and Weil also discussed and finalized drafts of the voting agreement with representatives of Hudson’s outside counsel. At the conclusion of these discussions, the parties had agreed on the final form of the merger agreement, which had no material changes from the draft sent by representatives of Weil to representatives of King & Spalding on June 12, 2025, the voting agreement and the other transaction documents.

On June 15, 2025, the Board held a meeting with members of Cantaloupe’s management and representatives of King & Spalding and J.P. Morgan present. Prior to the meeting, the Board received copies of the proposed merger agreement with 365, the form of voting agreement and the other transaction documents, as well as presentation materials prepared by representatives of King & Spalding and J.P. Morgan. Representatives of King & Spalding informed the Board that the material terms of the merger agreement had not changed since the Board meeting on June 13, 2025. In addition, representatives of King & Spalding reviewed with the Board, including the members of the Compensation Committee of the Board, certain compensation matters related to the merger agreement, including certain retention, compensation and benefits-related matters. J.P. Morgan reviewed its financial analyses of the merger consideration provided for in the merger agreement. Following its presentation, J.P. Morgan delivered to the Board its oral opinion, which was subsequently confirmed by delivery of a written opinion, dated June 15, 2025, to the effect that, as of such date, and based upon and subject to the assumptions made, procedures followed, matters considered and limitations on the review undertaken by J.P. Morgan in preparing its opinion, the merger consideration to be paid to the holders (other than the Excluded Shareholders) of common stock in the proposed Merger was fair, from a financial point of view, to such holders, as more fully described below in the section of this proxy statement titled “The Merger—Opinion of Cantaloupe’s Financial Advisor”. Representatives of J.P. Morgan also confirmed that there had been no changes to J.P. Morgan’s relationship disclosures as provided to the Board on June 13, 2025. Following these discussions and the delivery of the presentations, and after careful review and discussion by the Board, including consideration of the factors described below under the heading “The Merger—Recommendation of the Board and Reasons for the Merger” beginning on page 39 of this proxy statement, the Board unanimously determined that the merger agreement and the transactions contemplated thereby, including the Merger, were in the best interests of Cantaloupe and approved, adopted and declared advisable the merger agreement and the transactions contemplated thereby, including the Merger.

Following the Board meeting on June 15, 2025, Cantaloupe and 365 executed and delivered the Merger Agreement and related transaction agreements. 365 also entered into the Voting Agreements with Hudson and each member of the Board contemporaneously with the execution of the Merger Agreement.

On June 16, 2025, before the commencement of trading hours, Cantaloupe and 365 issued a joint press release announcing the Merger.

After careful consideration, as described above in the section of this proxy statement titled “The Merger—Background of the Merger”, the Board unanimously (i) determined that the Merger Agreement and the transactions contemplated thereby, including the Merger, are in the best interests of Cantaloupe, (ii) approved, adopted and declared advisable the Merger Agreement and the transactions contemplated thereby, including the Merger, (iii) recommended the approval and adoption of the Merger Agreement by Cantaloupe’s shareholders and (iv) directed that the Merger Agreement be submitted to Cantaloupe’s shareholders for their vote to adopt the Merger Agreement at a duly convened meeting of Cantaloupe’s shareholders.

In evaluating the Merger Agreement and the transactions contemplated thereby, including the Merger, the Board consulted with Cantaloupe’s executive management team, J.P. Morgan and King & Spalding. In the course of

reaching its determination, the Board considered a number of factors and benefits of the Merger, including the following factors weighing in favor of approving the Merger Agreement (not necessarily in order of relative importance):

The Board also considered a variety of risks and other potentially negative factors concerning the Merger and the Merger Agreement, including the following risks and factors (not necessarily in order of relative importance):

The Board concluded that the uncertainties, risks and potentially negative factors relevant to the Merger were outweighed by the potential benefits of the Merger.

The foregoing discussion of the factors considered by the Board set forth the principal factors considered by the Board but is not intended to be exhaustive. The Board collectively reached the unanimous conclusion to approve the Merger and the Merger Agreement considering all of the various factors described above and other factors that each member of the Board deemed relevant. In view of the wide variety of factors considered by the members of the Board in connection with their evaluation of the Merger and the complexity of these matters, the Board did not consider it practical, and did not attempt, to quantify, rank or otherwise assign relative weights to the specific factors it considered in reaching its decision. The Board made its decision based on the totality of information presented to and considered by it. In considering the factors discussed above, individual directors may have given different weights to different factors.

This explanation of the reasoning of the Board and certain information presented in this section of this proxy statement is forward-looking in nature and should be read in light of the factors set forth in the section of this proxy statement titled “Cautionary Statement Regarding Forward-Looking Information”.

Pursuant to an engagement letter, Cantaloupe retained J.P. Morgan as its financial advisor in connection with the proposed Merger.

At the meeting of the Board on June 15, 2025, J.P. Morgan rendered its oral opinion to the Board to the effect that, as of such date, and based upon and subject to the assumptions made, procedures followed, matters considered and limitations on the review undertaken by J.P. Morgan in preparing its opinion, the merger consideration to be paid to the holders (other than the Excluded Shareholders) of common stock in the proposed Merger was fair, from a financial point of view, to such holders. J.P. Morgan confirmed its June 15, 2025 oral opinion by delivering its written opinion, dated June 15, 2025, to the Board that, as of such date, the merger consideration to be paid to the holders (other than the Excluded Shareholders) of common stock in the proposed Merger was fair, from a financial point of view, to such holders.

The full text of the written opinion of J.P. Morgan, dated June 15, 2025, which sets forth, among other things, the assumptions made, procedures followed, matters considered and limitations on the review undertaken by J.P. Morgan in preparing its opinion, is attached as Annex B to this proxy statement and is incorporated herein by reference. The summary of the opinion of J.P. Morgan set forth in this proxy statement is qualified in its entirety by reference to the full text of such opinion. Cantaloupe’s shareholders are urged to read the opinion in its entirety. J.P. Morgan’s opinion was addressed to the Board (in its capacity as such) in connection with and for the purposes of its evaluation of the proposed Merger, and was limited to the fairness, from a financial point of view, of the consideration to be paid to the holders (other than the Excluded Shareholders) of common stock in the proposed Merger. J.P. Morgan expressed no opinion as to the fairness of any consideration to be paid in connection with the proposed Merger to the holders of any other class of securities, creditors or other constituencies of Cantaloupe or as to the underlying decision by Cantaloupe to engage in the proposed Merger. The issuance of J.P. Morgan’s opinion was approved by a fairness opinion committee of J.P. Morgan. The summary of the opinion of J.P. Morgan set forth in this proxy statement is qualified in its entirety by reference to the full text of such opinion. The opinion does not constitute a recommendation to any shareholder of Cantaloupe as to how such shareholder should vote with respect to the proposed Merger or any other matter.

In arriving at its opinion, J.P. Morgan, among other things:

In addition, J.P. Morgan held discussions with certain members of the management of Cantaloupe with respect to certain aspects of the proposed Merger, and the past and current business operations of Cantaloupe, the financial condition and future prospects and operations of Cantaloupe, and certain other matters J.P. Morgan believed necessary or appropriate to its inquiry.

In giving its opinion, J.P. Morgan relied upon and assumed the accuracy and completeness of all information that was publicly available or was furnished to or discussed with J.P. Morgan by Cantaloupe or otherwise reviewed by or for J.P. Morgan. J.P. Morgan did not independently verify any such information or its accuracy or completeness and, pursuant to J.P. Morgan’s engagement letter with Cantaloupe, J.P. Morgan did not assume any obligation to undertake any such independent verification. J.P. Morgan did not conduct and was not provided with any valuation or appraisal of any assets or liabilities, nor did J.P. Morgan evaluate the solvency of Cantaloupe or 365 under any applicable laws relating to bankruptcy, insolvency or similar matters. In relying on financial analyses and forecasts provided to J.P. Morgan or derived therefrom, J.P. Morgan assumed that they were reasonably prepared based on assumptions

reflecting the best currently available estimates and judgments by Cantaloupe’s management as to the expected future results of operations and financial condition of Cantaloupe to which such analyses or forecasts relate. J.P. Morgan expressed no view as to such analyses or forecasts or the assumptions on which they were based. J.P. Morgan also assumed that the proposed Merger and the other transactions contemplated by the Merger Agreement will be consummated as described in the Merger Agreement. J.P. Morgan also assumed that the representations and warranties made by Cantaloupe, 365, Holdco, Holdco II and Merger Subsidiary in the Merger Agreement and the related agreements were and will be true and correct in all respects material to its analysis. J.P. Morgan is not a legal, regulatory or tax expert and relied on the assessments made by advisors to Cantaloupe with respect to such issues. J.P. Morgan further assumed that all material governmental, regulatory or other consents and approvals necessary for the consummation of the proposed Merger will be obtained without any adverse effect on Cantaloupe or on the contemplated benefits of the proposed Merger.

The Management Projections (as defined in the section of this proxy statement titled “The Merger—Management Projections”) furnished to J.P. Morgan were prepared by Cantaloupe’s management as discussed more fully in the section of this proxy statement titled “The Merger—Management Projections” beginning on page 49 of this proxy statement. Cantaloupe does not publicly disclose internal management projections of the type provided to J.P. Morgan in connection with J.P. Morgan’s analysis of the proposed Merger, and such projections were not prepared with a view toward public disclosure. The Management Projections were based on numerous variables and assumptions that are inherently uncertain and may be beyond the control of Cantaloupe’s management, including, without limitation, factors related to general economic and competitive conditions, prevailing interest rates, and other factors as set forth in the section of this proxy statement titled “Cautionary Statement Regarding Forward-Looking Information” beginning on page 21 of this proxy statement. Accordingly, actual results could vary significantly from those set forth in the Management Projections. For more information regarding the use of projections and other forward-looking statements, please refer to the section of this proxy statement titled “The Merger—Management Projections” beginning on page 49 of this proxy statement.

J.P. Morgan’s opinion was necessarily based on economic, market and other conditions as in effect on, and the information made available to J.P. Morgan as of, the date of such opinion. J.P. Morgan’s opinion noted that subsequent developments may affect J.P. Morgan’s opinion and that J.P. Morgan does not have any obligation to update, revise or reaffirm such opinion. J.P. Morgan’s opinion is limited to the fairness, from a financial point of view, of the merger consideration to be paid to the holders (other than the Excluded Shareholders) of common stock in the proposed Merger, and J.P. Morgan has expressed no opinion as to the fairness of any consideration paid in connection with the proposed Merger to the holders of any other class of securities, creditors or other constituencies of Cantaloupe or as to the underlying decision by Cantaloupe to engage in the proposed Merger. J.P. Morgan also expressed no opinion with respect to the amount or nature of any consideration or compensation received by the Excluded Shareholders. Furthermore, J.P. Morgan expressed no opinion with respect to the amount or nature of any compensation to any officers, directors or employees of any party to the proposed Merger, or any class of such persons relative to the merger consideration to be paid to the holders of common stock in the proposed Merger or with respect to the fairness of any such compensation.

The terms of the Merger Agreement, including the merger consideration, were determined through arm’s length negotiations between Cantaloupe, Providence and 365, and the decision to enter into the Merger Agreement was solely that of the Board. J.P. Morgan’s opinion and financial analyses were only one of the many factors considered by the Board in its evaluation of the proposed Merger and should not be viewed as determinative of the views of the Board or Cantaloupe’s management with respect to the proposed Merger or the merger consideration.

In accordance with customary investment banking practice, J.P. Morgan employed generally accepted valuation methodologies in rendering its opinion to the Board on June 15, 2025 and in the financial analyses presented to the Board on such date in connection with the rendering of such opinion. The following is a summary of the material financial analyses utilized by J.P. Morgan in connection with rendering its opinion to the Board and does not purport to be a complete description of the analyses or data presented by J.P. Morgan. Some of the summaries of the financial analyses include information presented in tabular format. The tables are not intended to stand alone, and in order to more fully understand the financial analyses used by J.P. Morgan, the tables must be read together with the full text of each summary. Considering the data set forth below without considering the full narrative description of the financial analyses, including the methodologies and assumptions underlying the analyses, could create a misleading or incomplete view of J.P. Morgan’s analyses.

These companies were selected by J.P. Morgan, among other reasons, because they are publicly traded companies with operations and businesses that, for purposes of J.P. Morgan’s analysis, J.P. Morgan considered to be similar to those of Cantaloupe. However, certain of these companies may have characteristics that are materially different from those of Cantaloupe. The analyses necessarily involve complex considerations and judgments concerning differences in financial and operational characteristics of the companies involved and other factors that could affect the selected companies differently than they would affect Cantaloupe.

Using publicly available information, J.P. Morgan calculated, for each selected company, (i) the multiple of the firm value (calculated as fully diluted equity value, plus net debt, preferred equity and non-controlling interests and less unconsolidated investments, as applicable) (which we refer to as the “FV”) to the analyst consensus estimates of calendar year 2025 adjusted EBITDA for the applicable company (which we refer to as the “FV/2025E Adj. EBITDA Multiple”), (ii) the multiple of the FV to the analyst consensus estimates of calendar year 2026 adjusted EBITDA (which we refer to as the “2026E Adj. EBITDA”) for the applicable company (which we refer to as the “FV/2026E Adj. EBITDA Multiple”) and (iii) the multiple of the FV to the unlevered free cash flow (calculated as 2026E Adj. EBITDA minus unlevered cash taxes, change in net working capital and capital expenditures) for the applicable company (which we refer to as the “FV/2026E uFCF Multiple”).

Based on the results of this analysis, J.P. Morgan (i) selected a FV/2025E Adj. EBITDA Multiple reference range for Cantaloupe of 11.0x to 14.0x and applied such reference range to Cantaloupe’s projected adjusted EBITDA for calendar year 2025, (ii) selected a FV/2026E Adj. EBITDA Multiple reference range for Cantaloupe of 8.5x to 12.5x and applied such reference range to Cantaloupe’s projected adjusted EBITDA for calendar year 2026 and (iii) selected a FV/2026E uFCF Multiple reference range for Cantaloupe of 8.5x to 15.5x and applied such reference range to Cantaloupe’s projected unlevered free cash flows for calendar year 2026, in each case as provided in the Management Projections. The analysis derived the following ranges of implied equity value per share of common stock (rounded to the nearest $0.25):

J.P. Morgan compared these ranges to (i) the unaffected share price of common stock of $8.37 on May 30, 2025 and (ii) the merger consideration of $11.20 per share of common stock.

None of the selected transactions reviewed was identical to the proposed Merger. However, the selected transactions were chosen because certain aspects of the transactions, for purposes of J.P. Morgan’s analysis, may be considered similar to the proposed Merger. The analyses necessarily involve complex considerations and judgments concerning differences in financial and operational characteristics of the companies involved and other factors that could affect the transactions differently than they would affect the proposed Merger.

Using publicly available information, J.P. Morgan calculated, for each selected transaction, the multiple of the target company’s FV implied in the relevant transaction to the target company’s estimated EBITDA for the next 12 months starting as of the date of announcement of the applicable transaction (which we refer to as the “FV/NTM EBITDA Multiple”).

Based on the results of this analysis, J.P. Morgan selected a FV/NTM EBITDA Multiple reference range for Cantaloupe of 11.5x to 19.0x. J.P. Morgan then applied such reference range to Cantaloupe’s projected adjusted EBITDA for the next 12 months as of March 31, 2025 provided in the Management Projections. The analysis indicated a range of implied equity value per share of common stock (rounded to the nearest $0.25) of approximately $9.00 to $15.25, which J.P. Morgan compared to (i) the unaffected share price of common stock of $8.37 on May 30, 2025 and (ii) the merger consideration of $11.20 per share of common stock.

Discounted Cash Flow Analysis. J.P. Morgan conducted a discounted cash flow analysis for the purpose of determining an implied fully diluted equity value per share for common stock. J.P. Morgan calculated the unlevered free cash flows that Cantaloupe is expected to generate during the last quarter of Cantaloupe’s fiscal year 2025 and Cantaloupe’s fiscal year 2026 through 2028 based on the Management Projections, as discussed more fully in the section of this proxy statement titled “The Merger—Management Projections” beginning on page 49 of this proxy statement, which were discussed with, and approved by, the Board for use by J.P. Morgan in connection with its financial analyses. J.P. Morgan also calculated a range of terminal values for Cantaloupe at the end of this period by applying terminal growth rates ranging from 2.5% to 3.5%, based on guidance provided by Cantaloupe’s management, to estimates of terminal unlevered free cash flows for Cantaloupe at the end of fiscal year 2028, as provided in the Management Projections.

J.P. Morgan then discounted the unlevered free cash flow estimates and the range of terminal values to present value as of March 31, 2025 using a range of discount rates from 9.25% to 10.75%, which range was chosen by J.P. Morgan based upon an analysis of the weighted average cost of capital of Cantaloupe. The present values of the unlevered free cash flow estimates and the range of terminal values were then adjusted for Cantaloupe’s net operating losses, as provided by Cantaloupe’s management, discounted to present value as of March 31, 2025 using a range of discount rates from 9.25% to 10.75%. This analysis indicated a range of implied per share equity value for common stock (rounded to the nearest $0.25) of approximately $9.75 to $13.50, which J.P. Morgan compared to (i) the unaffected share price of common stock of $8.37 on May 30, 2025 and (ii) the merger consideration of $11.20 per share of common stock.

particular analysis or combination of analyses described above were merely utilized to create points of reference for analytical purposes and should not be taken to be the view of J.P. Morgan with respect to the actual value of Cantaloupe. The order of analyses described does not represent the relative importance or weight given to those analyses by J.P. Morgan. In arriving at its opinion, J.P. Morgan did not attribute any particular weight to any analyses or factors considered by it and did not form an opinion as to whether any individual analysis or factor (positive or negative), considered in isolation, supported or failed to support its opinion. Rather, J.P. Morgan considered the totality of the factors and analyses performed in determining its opinion.

Analyses based upon forecasts of future results are inherently uncertain, as they are subject to numerous factors or events beyond the control of the parties and their advisors. Accordingly, forecasts and analyses used or made by J.P. Morgan are not necessarily indicative of actual future results, which may be significantly more or less favorable than suggested by those analyses. Moreover, J.P. Morgan’s analyses are not and do not purport to be appraisals or otherwise reflective of the prices at which businesses actually could be acquired or sold. None of the selected companies reviewed as described in the above summary is identical to Cantaloupe and none of the selected transactions reviewed as described in the above summary was identical to the proposed Merger. However, the companies selected were chosen by J.P. Morgan because they are publicly traded companies with operations and businesses that, for purposes of J.P. Morgan’s analysis, may be considered similar to those of Cantaloupe and the transactions selected were chosen by J.P. Morgan because certain aspects of the transactions, for purposes of J.P. Morgan’s analysis, may be considered similar to the proposed Merger. The analyses necessarily involve complex considerations and judgments concerning differences in financial and operational characteristics of the companies involved and other factors that could affect the companies compared to Cantaloupe and the transactions compared to the proposed Merger.

As a part of its investment banking business, J.P. Morgan and its affiliates are continually engaged in the valuation of businesses and their securities in connection with mergers and acquisitions, investments for passive and control purposes, negotiated underwritings, secondary distributions of listed and unlisted securities, private placements, and valuations for corporate and other purposes. J.P. Morgan was selected to advise Cantaloupe with respect to the proposed Merger and deliver an opinion to the Board with respect to the proposed Merger on the basis of, among other things, such experience and its qualifications and reputation in connection with such matters and its familiarity with Cantaloupe and the industries in which it operates.

For financial advisory services rendered in connection with the proposed Merger, Cantaloupe has agreed to pay J.P. Morgan an estimated fee of approximately $15 million, $2 million of which became payable to J.P. Morgan at the time J.P. Morgan delivered its opinion and the remainder of which is contingent and payable upon the consummation of the proposed Merger. In addition, Cantaloupe has agreed to reimburse J.P. Morgan for certain of its expenses incurred in connection with its services, including the fees and disbursements of counsel, and will indemnify J.P. Morgan against certain liabilities arising out of J.P. Morgan’s engagement.

During the two years preceding the date of J.P. Morgan’s written opinion, J.P. Morgan and its affiliates have had commercial or investment banking relationships with Cantaloupe, for which J.P. Morgan and its affiliates have received customary compensation. Such services during such period have included acting as joint lead arranger on credit facilities of Cantaloupe in January 2025. In addition, J.P. Morgan’s commercial banking affiliate is an agent bank and a lender under outstanding credit facilities of Cantaloupe, for which it receives customary compensation or other financial benefits. During the two years preceding the date of J.P. Morgan’s written opinion, the aggregate fees recognized by J.P. Morgan from Cantaloupe were less than $50,000. During the two years preceding the date of J.P. Morgan’s written opinion, J.P. Morgan and its affiliates have had commercial or investment banking relationships with Providence, a significant affiliate of 365, for which J.P. Morgan and its affiliates have received customary compensation. Such services during such period have included providing syndicated lending and financial advisory services to Providence portfolio companies. In addition, J.P. Morgan’s commercial banking affiliate is an agent bank and a lender under outstanding credit facilities of Providence portfolio companies. During the two years preceding the date of J.P. Morgan’s written opinion, the aggregate fees recognized by J.P. Morgan from Providence were approximately $10 million. J.P. Morgan and/or its affiliates are currently providing investment banking services to Providence and/or its affiliates, in connection with transactions that are unrelated to the proposed Merger. J.P. Morgan and/or its affiliates expect to receive customary compensation in connection with such investment banking services which, considered in the aggregate and assuming all the transactions are actually completed, are expected by J.P. Morgan to be less than the fee for financial advisory services that J.P. Morgan expects to receive from Cantaloupe in connection with the proposed Merger. During the two years preceding the date of J.P. Morgan’s written opinion,

neither J.P. Morgan nor its affiliates have had any material financial advisory or other material commercial or investment banking relationships with 365. In addition, J.P. Morgan and its affiliates hold, on a proprietary basis, less than 1% of the outstanding common stock of Cantaloupe. In the ordinary course of their businesses, J.P. Morgan and its affiliates actively trade the debt and equity securities or financial instruments (including derivatives, bank loans or other obligations) of Cantaloupe for their own account or for the accounts of customers and, accordingly, are likely at any time to hold long or short positions in such securities or other financial instruments.

In connection with the evaluation of Cantaloupe’s strategic alternatives described in this proxy statement, in February 2025, Cantaloupe’s management prepared certain preliminary, non-public, unaudited prospective financial projections for the fiscal years 2025 through 2028, which unaudited prospective financial projections were presented to the Transaction Committee and to the Board in connection with the Transaction Committee and the Board considering, analyzing and evaluating Cantaloupe’s strategic alternatives, including the Merger. Cantaloupe also provided such unaudited prospective financial projections to Cantaloupe’s financial advisor, J.P. Morgan. Cantaloupe also provided such unaudited prospective financial projections to 365 and other potential acquirors, in connection with their respective evaluations of a potential transaction with Cantaloupe. In May 2025, in connection with the review by Cantaloupe’s management of the financial results for the fiscal quarter ended March 31, 2025, Cantaloupe’s management updated such unaudited prospective financial information to reflect a downward adjustment to projected fiscal year 2025 revenue of approximately $5 million, which adjustment was based on the actual results of Cantaloupe through March 31, 2025. We refer to these financial projections as the “Management Projections”. Cantaloupe provided the Management Projections to J.P. Morgan for its use and reliance in connection with J.P. Morgan’s financial analyses and opinion and such use and reliance was approved by the Board, as more fully described in the section of this proxy statement titled “The Merger—Opinion of Cantaloupe’s Financial Advisor” above. Cantaloupe also provided the Management Projections to 365 and other potential acquirors in connection with their respective evaluations of a potential transaction with Cantaloupe.

The Management Projections described below were not prepared with a view towards public disclosure and, other than its quarterly financial guidance, Cantaloupe does not as a matter of course publicly disclose forecasts or internal projections as to future performance due to, among other things, the inherent difficulty of accurately predicting financial performance for future periods and the uncertainty, unpredictability and subjectivity of the underlying assumptions and estimates. The Management Projections are included in this proxy statement only because this information was prepared by Cantaloupe’s management and reviewed and approved by the Board for use and reliance by J.P. Morgan in connection with J.P. Morgan’s financial analyses and opinion, as more fully described in the section of this proxy statement titled “The Merger—Opinion of Cantaloupe’s Financial Advisor” above, and for the purpose of providing shareholders of Cantaloupe access to certain information made available to the Board in connection with its evaluation of the Merger. The Management Projections are not being included in this document to influence shareholders’ decisions regarding whether to vote for or against the Merger Proposal, or to influence any other investment decisions.

The Management Projections were also not prepared with a view to comply with generally accepted accounting principles as applied in the United States (which we refer to as “GAAP”), the published guidelines of the SEC regarding projections or the guidelines established by the American Institute of Certified Public Accountants for preparation and presentation of prospective financial information. For example, the Management Projections do not include footnote disclosures as may be required by GAAP.

The Management Projections include forecasts provided to J.P. Morgan and the Board in connection with a potential business combination transaction, and as such are excluded from the definition of “non-GAAP financial measures” under SEC rules. Therefore such projections are not subject to SEC rules regarding disclosures of non-GAAP financial measures, which would otherwise require a reconciliation of a non-GAAP financial measure to a GAAP financial measure. In addition, reconciliations of non-GAAP financial measures were not included in the Management Projections provided to or relied upon by J.P. Morgan or the Board for purposes of their respective evaluations. Accordingly, we have not provided a reconciliation of the financial measures included in the Management Projections to the relevant GAAP financial measures. The non-GAAP financial measures are not meant to be considered in isolation or as a substitute for comparable GAAP measures. These non-GAAP financial measures have not been prepared in accordance with GAAP, are not reported by all of Cantaloupe’s competitors and may not be directly comparable to similarly titled measures of Cantaloupe’s competitors due to potential differences in the exact method of calculation.

The Management Projections included in this proxy statement have been prepared by, and are the responsibility of, our management. None of Deloitte & Touche LLP, Cantaloupe’s independent registered public accounting firm,

BDO USA, P.C. nor any other independent registered public accounting firm has audited, reviewed, examined, compiled or applied agreed-upon procedures with respect to the Management Projections, nor have they expressed any opinion or any other form of assurance on the Management Projections or their achievability, and assume no responsibility for, and disclaim any association with, the Management Projections. The reports of each of Deloitte & Touche LLP and BDO USA, P.C. contained in Cantaloupe’s Annual Report on Form 10-K for the fiscal year ended June 30, 2024, incorporated by reference into this proxy statement, relate to Cantaloupe’s previously issued financial statements and do not extend to the Management Projections, and should not be read to do so.

Although presented in the table below with numerical specificity, the Management Projections reflect numerous estimates and assumptions with respect to industry performance, general business, economic, market and financial conditions, foreign exchange rates, changes to our business, financial condition or results of operations, and other matters. Many of these estimates and assumptions are difficult to predict, subject to significant economic and competitive uncertainties, are beyond our control, and may cause the Management Projections or the underlying assumptions to be inaccurate, including the factors described or referenced in the section of this proxy statement titled “Cautionary Statement Regarding Forward-Looking Information” beginning on page 21 of this proxy statement. The Management Projections also reflect assumptions as to certain business decisions that are subject to change. There can be no assurance that the underlying assumptions would prove to be accurate or that the projected results would be realized, and actual results could differ materially from those reflected in the Management Projections, whether or not the Merger is completed. Since the Management Projections cover multiple years, the information contained therein, and the estimates and assumptions on which such forecasts are based, by their nature become even less reliable with each successive year. The Management Projections also do not take into account any circumstances or events occurring after the date they were prepared; thus, resulting in further reasons why there can be no assurance that the Management Projections will be realized or that our actual results will not be significantly higher or lower than projected. Further, the Management Projections were prepared by Cantaloupe’s management and represent their evaluation of expected future financial performance of Cantaloupe on a stand-alone basis, without reference to the Merger. The Management Projections reflect numerous variables, expectations and assumptions as to certain business decisions that are subject to change and do not take into account any circumstances or events occurring after the date they were prepared, including the transactions contemplated by the Merger Agreement or the possible financial and other effects on Cantaloupe of the Merger, and do not attempt to predict or suggest future results of the surviving corporation or give effect to the Merger, including the effect of negotiating or executing the Merger Agreement, the costs that may be incurred in connection with consummating the Merger, the potential synergies that may be achieved as a result of the Merger, the effect on Cantaloupe of any business or strategic decision or action that has been or will be taken as a result of the Merger Agreement having been executed, or the effect of any business or strategic decisions or actions which would likely have been taken if the Merger Agreement had not been executed, but which were instead altered, accelerated, postponed or not taken in anticipation of the Merger. Further, the Management Projections do not take into account the effect of any possible failure of the Merger to occur. No assurances can be given that, if the Management Projections and the underlying assumptions had been prepared as of the date of this proxy statement, similar assumptions would be used.

None of Cantaloupe or its affiliates, officers, directors, advisors or other representatives has made or makes any representation to any Cantaloupe shareholder or other person regarding the information included in the Management Projections or Cantaloupe’s ultimate performance compared to the information contained in the Management Projections or that forecasted results will be achieved. Cantaloupe has made no representation to 365, in the Merger Agreement or otherwise, concerning the Management Projections.

The Management Projections reflect numerous estimates and assumptions with respect to industry performance, general business, economic, market and financial conditions, foreign exchange rates, changes to our business, financial condition or results of operations, and other matters. In particular, the Cantaloupe management team considered the following estimates and hypothetical assumptions with respect to the development of the Management Projections:

For the foregoing reasons, as well as the bases and assumptions on which the Management Projections were compiled, the inclusion of specific portions of the Management Projections in this proxy statement should not be regarded as an indication that such forecasts will be an accurate prediction of future events, and they should not be relied on as such. Neither Cantaloupe nor 365 or their respective affiliates, officers, directors, advisors or other representatives can provide any assurance that actual results will not differ from the Management Projections. Except as may be required by applicable securities laws, we do not intend to update or otherwise revise the Management Projections or the specific portions presented to reflect circumstances existing after the date when made or to reflect the occurrence of future events.

The Management Projections are forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. For information on factors that may cause our future financial results to materially vary, see the section of this proxy statement titled “Cautionary Statement Regarding Forward-Looking Information” above.

A summary of the Management Projections is set forth in the following table, which Management Projections were prepared by Cantaloupe’s management to help develop a framework for evaluating the potential future value and financial outlook of Cantaloupe for the fiscal years ending June 30, 2025, 2026, 2027 and 2028.

We anticipate that the total amount of funds necessary to complete the transactions contemplated by the Merger Agreement, and to pay related fees and expenses, will be approximately $945 million. This amount includes funds needed to pay the Transaction Amounts.

365 has obtained committed Debt Financing to be provided by the Lender Parties pursuant to the terms and conditions of the Debt Commitment Letter. In connection with the Merger Agreement, 365 has delivered to Cantaloupe a copy of the Debt Commitment Letter.

The obligations of the Lender Parties to provide Debt Financing under the Debt Commitment Letter are subject to a number of customary conditions, including the substantially concurrent consummation of the Merger. For more information, please see the section of this proxy statement titled “The Merger Agreement—Debt Financing”.

The closing of the Merger will occur at 8:00 a.m., Eastern time, as soon as possible, but in any event no later than five business days following the date the conditions set forth in the Merger Agreement (other than those conditions that by their nature are to be satisfied at the closing, but subject to the satisfaction or, to the extent permissible, waiver

of those conditions at the closing) have been satisfied or, to the extent permissible, waived by the party or parties entitled to the benefit of such conditions, or at such other time or on such other date as Cantaloupe and 365 may mutually agree in writing.

On the closing date, Cantaloupe, 365, Holdco, Holdco II and Merger Subsidiary will cause (i) a statement of merger in such form as required by the PBCL to be properly executed and filed with the Department of State of the Commonwealth of Pennsylvania and (ii) a certificate of merger in such form as required by the DGCL relating to the Merger to be properly executed and filed with the Secretary of State of the State of Delaware, and will make all other filings or recordings required by applicable law, in each case in such form as is reasonably satisfactory to both 365 and Cantaloupe. The Merger will become effective at such time agreed to by Cantaloupe, 365, Holdco, Holdco II and Merger Subsidiary, which will be as soon as practicable following the filing of both of the statement of merger and the certificate of merger and will be expressly stated in such filings, or at such later time that Cantaloupe, 365, Holdco, Holdco II and Merger Subsidiary may agree and designate in the statement of merger and certificate of merger as the effective time of the Merger.

Promptly after the effective time of the Merger (and after receipt by the Paying Agent (as defined in the section of this proxy statement titled “The Merger Agreement—Payment for Cantaloupe’s Common Stock”) from Cantaloupe’s transfer agent of all information reasonably necessary to enable the Paying Agent to effect the mailing; provided that 365 and the surviving corporation will use reasonable best efforts to obtain such information to enable such mailing to occur no later than the fifth business day following the effective time of the Merger), 365 must send, or cause the Paying Agent to send, to each holder of record of shares of common stock at the effective time of the Merger a letter of transmittal (in a form that was reasonably acceptable to Cantaloupe prior to the effective time of the Merger) and instructions (which will specify that the delivery will be effected, and risk of loss and title will pass, only upon proper delivery of the certificates representing shares of common stock (which we refer to as the “Certificates”) or transfer of uncertificated shares of common stock represented in book entry, including through Cede & Co., the nominee of DTC (which we refer to as the “Uncertificated Shares”) to the Paying Agent) for use in such exchange.

Each holder of shares of common stock that have been converted into the right to receive the merger consideration will be entitled to receive, upon (i) surrender to the Paying Agent of a Certificate, together with a properly completed letter of transmittal (or affidavit in lieu of lost, stolen or destroyed Certificates), or (ii) receipt of an “agent’s message” by the Paying Agent (or such other evidence, if any, of transfer that the Paying Agent may reasonably request) in the case of a book-entry transfer of Uncertificated Shares, the merger consideration in respect of each share of common stock represented by a Certificate or Uncertificated Share. Until so surrendered or transferred, as the case may be, each such Certificate or Uncertificated Share will represent after the effective time of the Merger for all purposes only the right to receive the merger consideration, without interest thereon.

For more information about the payment of the merger consideration and surrender of stock certificates, see the section of this proxy statement titled “The Merger Agreement—Payment for Cantaloupe’s Common Stock”.

In considering the Board’s unanimous recommendation that you vote to approve the proposal to approve and adopt the Merger Agreement, you should be aware that Cantaloupe’s directors and executive officers may have interests in the Merger that are different from, or in addition to, the interests of Cantaloupe shareholders generally. The Board was aware of the different or additional interests set forth in this proxy statement and considered such interests along with other matters in approving the Merger Agreement and the transactions contemplated by the Merger Agreement, including the Merger. The transactions contemplated by the Merger Agreement will constitute a “change in control” for purposes of our executive compensation and benefit plans and agreements described below. These potential interests are described below.

At or immediately prior to the effective time of the Merger, each Cantaloupe RSU that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe RSU, become fully vested and free of restrictions and will be canceled and converted into the right to receive, in accordance with the terms of the Merger Agreement, an amount in cash equal to the merger consideration.

At or immediately prior to the effective time of the Merger, each Cantaloupe PSU that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe PSU, become vested with respect to that number of shares of common stock based on deemed achievement of the performance metrics at target performance. Immediately thereafter, Cantaloupe PSUs will be canceled and converted into the right to receive, with respect to each such vested share of common stock underlying such Cantaloupe PSU, in accordance with the terms of the Merger Agreement, an amount in cash equal to the merger consideration.

At or immediately prior to the effective time of the Merger, each Cantaloupe Restricted Stock Award that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe Restricted Stock Award, become fully vested and free of restrictions and will be canceled and converted into the right to receive, in accordance with the terms of the Merger Agreement, an amount in cash equal to the merger consideration.

At or immediately prior to the effective time of the Merger, each In-the-Money Option that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe Option, become fully vested and free of restrictions and be canceled in exchange for cash in an amount equal to (i) the total number of shares of common stock for which such Cantaloupe Option is exercisable, multiplied by (ii) the excess of the merger consideration over the per share exercise price of such Cantaloupe Option. At the effective time of the Merger, each Out-of-the-Money Option that is outstanding immediately prior to the effective time of the Merger will be canceled without consideration and will be of no further force and effect.

The Board has granted permission for 365 to engage in discussions with certain executive officers of Cantaloupe, including with respect to (i) their continuing employment with 365 or its affiliates, including the surviving corporation, from and after the effective time of the Merger, and appropriate severance arrangements for employees whose employment with 365 or its affiliates may not continue, (ii) a potential equity investment in 365 or its affiliates in connection with the Merger and (iii) incentive equity arrangements of 365 or its affiliates from and after the effective time of the Merger, including the allocation of any go-forward incentive equity “pool”.

In addition, at or prior to the effective time of the Merger, our directors and executive officers may enter into rollover agreements with 365, Holdco, Holdco II or Merger Subsidiary and contribute their shares of Cantaloupe stock to 365, Holdco, Holdco II or Merger Subsidiary, which shares of Cantaloupe stock will be subject to the treatment specified under the rollover agreement applicable to such rollover shares.

Following the execution of the Merger Agreement, representatives of 365 have had preliminary discussions with Douglas G. Bergeron, Chairman of the Board, regarding a potential rollover arrangement with respect to shares of Cantaloupe’s common stock held by Mr. Bergeron, which shares are expected to be rollover shares for purposes of the Merger Agreement. As of [ ], 2025, the record date for the Special Meeting, Mr. Bergeron beneficially owned 1,152,559 shares of common stock, representing approximately [ ]% of the voting power of the shares of Cantaloupe stock outstanding as of the record date and entitled to vote at the Special Meeting. Based on preliminary discussions held to date, 365 expects that, prior to the closing of the Merger, Mr. Bergeron will enter into a rollover agreement with 365 or one of its affiliates with respect to shares of common stock held by him. However, as of the date of this proxy statement, there is no understanding as to the amount of shares of Cantaloupe’s common stock that would be subject to such rollover arrangement, and no definitive agreement has been entered into between Mr. Bergeron and 365 or its affiliates regarding such potential rollover, and there can be no assurances that the terms of any such agreement will be agreed upon with Mr. Bergeron. If Mr. Bergeron and 365 or its affiliates enter into a rollover agreement, Mr. Bergeron will not receive the merger consideration in respect of any rollover shares held by him and instead such shares will, immediately prior to the effective time of the Merger, be subject to the treatment specified under the rollover agreement applicable to such rollover shares. Based on preliminary discussions held to date, if Mr. Bergeron and 365 or its affiliates enter into a rollover agreement, Mr. Bergeron may obtain a seat on the board of directors of an affiliate of Providence that will oversee the management of 365 following the closing of the Merger.

Other than as described above, as of the date of this proxy statement, none of Cantaloupe’s directors or executive officers has entered into any new agreement, arrangement or understanding with 365 or any of its affiliates regarding the terms and conditions of compensation, incentive pay or employment with Cantaloupe after the Merger or any

rollover agreement. Prior to or following the effective time of the Merger, however, certain of Cantaloupe’s directors or executive officers may enter into rollover agreements or new agreements and/or amendments to existing employment or compensation arrangements with 365 or one of its affiliates regarding their employment with the surviving corporation or its affiliates after the Merger.

Certain of our employees received cash bonuses (which we refer to as “Transaction Bonuses”). Two named executive officers received such Transaction Bonuses in the following amounts: (i) Scott Stewart received a Transaction Bonus of $200,000, and (ii) Anna Novoseletsky received a Transaction Bonus of $100,000. These Transaction Bonuses will be repayable to Cantaloupe if the closing of the Merger does not occur.

Our named executive officers are party to employment arrangements or offer letters with Cantaloupe. Certain of these arrangements provide our named executive officers with severance protection in the case of a termination without “cause” or, in certain cases, a resignation for “good reason”, which in certain cases is enhanced if such termination occurs in connection with a “change of control”. The employment arrangements and offer letters which provide severance protections to our executive officers are described in further detail below.

Mr. Venkatesan originally entered into an employment agreement with Cantaloupe in connection with his appointment as Chief Operating Officer to be effective February 4, 2022 (which we refer to as the “Original Venkatesan Employment Agreement”). Mr. Venkatesan later entered into a promotion letter with Cantaloupe, effective as of September 30, 2022, in connection with his appointment as Chief Executive Officer, which amended certain parts of the Original Venkatesan Employment Agreement (which we refer to as the “Promotion Letter” and together with the Original Venkatesan Employment Agreement, the “Venkatesan Employment Agreement”). Pursuant to the Venkatesan Employment Agreement, if Mr. Venkatesan is terminated by us without “cause”, or resigns his employment for “good reason”, in each case, within 24 months following a “change of control”, then, subject to his execution of a release of claims and continued compliance with the covenants in the Venkatesan Employment Agreement, Mr. Venkatesan will be provided a lump sum payment equal to (i) his base salary (without giving effect to any reduction that is the basis for any resignation for “good reason”) plus (ii) an amount equal to the last annual bonus paid in the fiscal year completed prior to such termination. In addition, if Mr. Venkatesan becomes entitled to receive payments, benefits or distributions that would be subject to the excise tax under Section 4999 of the Internal Revenue Code of 1986, as amended, such payments, benefits and distributions would be reduced such that the excise tax does not apply, unless Mr. Venkatesan would be better off on an after-tax basis receiving all of the payments, benefits and distributions and paying the applicable excise tax.

The Venkatesan Employment Agreement contains customary restrictive covenants, including perpetual confidentiality and non-disparagement covenants, and intellectual property covenants, as well as a non-compete, non-solicit of customers and suppliers and non-solicit of employees (including a no-hire) that each apply during employment and for two years following any termination.

In connection with his appointment as our Chief Financial Officer, Cantaloupe entered into an employment agreement with Mr. Stewart, effective February 4, 2022 (which we refer to as the “Stewart Employment Agreement”). Pursuant to the Stewart Employment Agreement, if Mr. Stewart is terminated by us without “cause”, or resigns his employment for “good reason”, within 24 months following a “change of control”, then, subject to his execution of a release of claims and continued compliance with the covenants in the Stewart Employment Agreement, Mr. Stewart will be provided (i) a lump sum payment equal to his base salary (without giving effect to any reduction that is the basis for any resignation for “good reason”) plus (ii) an amount equal to the last annual bonus paid in the fiscal year completed prior to such termination. In addition, if Mr. Stewart becomes entitled to receive payments, benefits or distributions that would be subject to the excise tax under Section 4999 of the Internal Revenue Code of 1986, as amended, such payments, benefits and distributions would be reduced such that the excise tax does not apply, unless Mr. Stewart would be better off on an after-tax basis receiving all of the payments, benefits and distributions and paying the applicable excise tax.

The Stewart Employment Agreement contains customary restrictive covenants, including perpetual confidentiality and non-disparagement covenants, and intellectual property covenants, as well as a non-compete, non-solicit of customers and suppliers and non-solicit of employees (including a no-hire) that each apply during employment and for two years following any termination.

Mr. Dumbrell entered into an offer letter with Cantaloupe in connection with his appointment as our Chief Revenue Officer effective as of December 22, 2021. If Mr. Dumbrell is terminated by us for any reason other than for “cause”, and subject to his execution of a general release of claims and separation agreement, Mr. Dumbrell is eligible to receive a severance package consisting of six months of continued base salary.

Mr. Dumbrell’s offer letter contains customary restrictive covenants, including perpetual confidentiality covenants, as well as a non-solicit of customers that applies during employment and during any severance period following any termination.

Mr. Singal entered into an offer letter with Cantaloupe in connection with his appointment as our Chief Technology Officer effective as of October 27, 2022. If Mr. Singal is terminated by us for any reason other than for “cause” or death, and subject to his execution of a general release of claims and separation agreement, Mr. Singal is eligible to receive a severance package consisting of six months of continued base salary.

Mr. Singal’s offer letter contains customary restrictive covenants, including perpetual confidentiality covenants, as well as a non-solicit of customers, non-solicit of employees (including a no-hire) and non-compete that each apply for a one-year period following any termination.

Ms. Novoseletsky entered into an offer letter with Cantaloupe in connection with her appointment as our Chief Legal and Compliance Officer effective as of January 17, 2023. If Ms. Novoseletsky is terminated by us for any reason other than for “cause” or death, and subject to her execution of a general release of claims and separation agreement, Ms. Novoseletsky is eligible to receive a severance package consisting of six months of continued base salary.

Ms. Novoseletsky’s offer letter contains customary restrictive covenants, including perpetual confidentiality covenants, as well as a non-solicit of customers, non-solicit of employees (including a no-hire), and non-compete that each apply for a one-year period following any termination.

Mr. Grachek entered into an offer letter with Cantaloupe in connection with his appointment as our Chief Accounting Officer effective as of May 15, 2023. The offer letter does not contain any severance commitments.

Mr. Grachek’s offer letter does contain customary restrictive covenants, including perpetual confidentiality covenants, as well as a non-solicit of customers, non-solicit of employees (including a no-hire) and non-compete that each apply for a one-year period following any termination.

Between June 15, 2025 and closing of the Merger, Cantaloupe may modify the compensation of current employees in the ordinary course of business consistent with past practice by: (i) increasing annual base salaries (and target bonuses as a result of the corresponding increase in base salaries to the extent the target bonus is stated as a percentage of annual base salary) at the end of the fiscal year in an amount that does not exceed 4% of the applicable employee’s annual base salary on a year-over-year basis; and (ii) making annual modifications to health and welfare plans for the 2026 plan year that do not materially increase the cost to Cantaloupe of maintaining such health and welfare plans. For the avoidance of doubt, such 4% cap will be inclusive of all annual base salary increases implemented by Cantaloupe after the date of the Merger Agreement, including, in respect of Cantaloupe’s ordinary course annual merit cycle and promotion.

Under the Merger Agreement, Cantaloupe will pay fiscal year 2025 annual bonuses in the ordinary course of business consistent with past practices based on actual level of performance attained. If the closing of the Merger occurs in

fiscal year 2026 but prior to the date on which Cantaloupe ordinarily would have paid fiscal year 2025 annual bonuses in the ordinary course of business consistent with past practice, Cantaloupe will, on the business day immediately preceding the closing of the Merger, pay fiscal year 2025 annual bonuses based on the actual level of performance attained.

Between June 15, 2025 and closing of the Merger, Cantaloupe may award 2026 annual bonuses to employees of Cantaloupe and its subsidiaries in the ordinary course of business consistent with past practice (including to named executive officers). If the closing date of the Merger occurs (i) after the close of fiscal year 2026 and (ii) following the date on which Cantaloupe ordinarily would have paid fiscal year 2026 annual bonuses in the ordinary course of business consistent with past practice, Cantaloupe will pay all accrued annual bonuses earned and payable for fiscal year 2026 in the ordinary course of business consistent with past practice based on the attained level of performance. If the closing of the Merger occurs (x) after the close of fiscal year 2026 and (y) prior to the date on which Cantaloupe ordinarily would have paid fiscal year 2026 annual bonuses in the ordinary course of business consistent with past practice, 365 will pay fiscal year 2026 annual bonuses in the ordinary course of business consistent with 365’s past practice based on the actual level of performance attained. If the closing date of the Merger occurs before the close of fiscal year 2026, 365 will pay all accrued annual bonuses earned and payable for fiscal year 2026 in the ordinary course of business consistent with past practice based on the actual level of performance attained.

Between June 15, 2025 and closing of the Merger, Cantaloupe may grant Cantaloupe equity awards (with an aggregate maximum number of 600,000 shares, of which a maximum number of 400,000 shares may be utilized for off-cycle grants) to employees of Cantaloupe and its subsidiaries in the ordinary course of business consistent with past practice (including to named executive officers and including with respect to individual and aggregate grant amounts and the allocation of awards) (which we refer to as the “2026 Equity Awards”); provided that (a) the 2026 Equity Awards will be granted pursuant to the forms of award agreements used for the awards granted by Cantaloupe during fiscal year 2025 to similarly situated employees, except that all of the 2026 Equity Awards will be in the form of time-based Cantaloupe equity awards and such award agreements will reflect the treatment in clause (b); and (b) on the closing date of the Merger, (i) the 2026 Equity Awards will vest on a prorated basis based on the total number of shares of our common stock subject to the 2026 Equity Award multiplied by a fraction equal to (x) the number of calendar days that have elapsed since the grant date of such award divided by (y) 1,095 and (ii) will be converted into the right to receive, in accordance with the terms of the Merger Agreement, an amount in cash equal to the merger consideration; provided however, all 2026 Equity Awards that are unvested as of 12:01 a.m., Eastern time, on the closing date of the Merger (after taking into account the vesting described in clause (i)) shall (1) be forfeited for no consideration immediately prior to the effective time of the Merger and (2) not be subject to the treatment of Cantaloupe equity awards set forth in the Merger Agreement. Unless otherwise provided by any offer letter, employment agreement, or employee benefit plan, if an employee terminates employment with Cantaloupe for any reason prior to closing of the Merger, such employee will forfeit all of his or her 2026 Equity Awards upon such termination.

Under the Merger Agreement, between June 15, 2025 and closing of the Merger, Cantaloupe may take such mitigation steps as are reasonably necessary to avoid any excess parachute payments under Section 280G of the Code and any excise taxes related thereto under Section 4999 of the Code following consultation with 365, including but not limited to, engaging an accounting or valuation firm (i) to perform calculations regarding Sections 280G and 4999 of the Code including, in consultation with 365, assigning value for reasonable post-closing compensation to restrictive covenants that continue following the closing of the Merger and accelerating the timing of payment of annual incentive plan awards that are earned in 2025 but may otherwise be payable in 2026, and (ii) to recommend 280G mitigation actions to reduce the amount of any potential “excess parachute payments” for “disqualified individuals” (each as defined in Section 280G of the Code), including the acceleration of vesting and/or payment of compensation or equity-based awards (which we refer to as, collectively, “280G Mitigation”), with the implementation of any 280G Mitigation strategies to be subject to the prior consent of 365 (not to be unreasonably withheld, conditioned or delayed). Cantaloupe may also amend existing employee benefit plans to incorporate “best after-tax cutback” provisions. For clarity, Cantaloupe will not provide for the gross-up or reimbursement of excise taxes payable under Section 4999 of the Code.

365 has agreed to cause the surviving corporation, and the surviving corporation has agreed to, provide certain indemnification and insurance to our directors and officers. For more information, see the section of this proxy statement titled “The Merger Agreement—Directors’ and Officers’ Indemnification and Insurance”.

In accordance with Item 402(t) of Regulation S-K promulgated under the Securities Act of 1933, as amended, the table below sets forth the amount of payments and benefits that each of our named executive officers would or may receive in connection with the Merger. The amounts reported below are based on various assumptions that may or may not actually occur or be accurate on the relevant date, including assumptions described in the footnotes to the table and the below:

The calculations in the table do not include amounts that Cantaloupe’s named executive officers were already entitled to receive or vested in as of the date of this proxy statement. In addition, these amounts do not attempt to forecast any additional equity award grants, issuances or forfeitures that may occur prior to the completion of the merger and do not reflect any Cantaloupe equity or other incentive awards that are expected to vest in accordance with their terms prior to the effective time of the Merger. As a result of the foregoing assumptions, which may or may not actually occur or be accurate on the relevant date, including the assumptions described in the footnotes to the table, the actual amounts, if any, to be received by a named executive officer may materially differ from the amounts set forth below.

For purposes of this disclosure, “single trigger” refers to benefits that arise solely as a result of the closing of the Merger and “double trigger” refers to benefits that arise as a result of the closing of the Merger accompanied by certain terminations, on or following the closing.

 

As further described in the section of this proxy statement titled “The Merger Agreement—Consents, Approvals and Filings”, in the United States, the Merger is subject to the expiration or termination of any applicable waiting periods under the HSR Act. Notification under the HSR Act was filed on [  ], 2025.

Outside of the United States, the Merger may be subject to the obtainment of consent of certain other regulatory authorities. The parties have agreed to use their reasonable best efforts to make the required filings as promptly as reasonably practicable, subject to cooperation between the parties pursuant to the Merger Agreement.

The following is a discussion of the material U.S. federal income tax consequences (i) to U.S. Holders and Non-U.S. Holders (each as defined below) of shares of our common stock who exchange those shares for cash pursuant to the Merger, and (ii) to U.S. Holders and Non-U.S. Holders (each as defined below) of shares of our preferred stock who receive the preferred stock redemption payment in redemption of those shares in connection with the Merger. This discussion is based on the provisions of the Internal Revenue Code (which we refer to as the “Code”), applicable U.S. Treasury regulations (which we refer to as, “Treasury Regulations”), judicial authorities and administrative interpretations, each as in effect as of the date of this proxy statement. These authorities are subject to change and differing interpretation, possibly on a retroactive basis, and any such change or interpretation could affect the accuracy of the statements and conclusions set forth in this discussion. We cannot assure you that the Internal Revenue Service (which we refer to as the “IRS”) will not challenge one or more of the tax consequences described in this discussion or that a court would not sustain such challenge.

This discussion applies only to shareholders who hold their shares of our common stock or preferred stock as a “capital asset” within the meaning of Section 1221 of the Code (generally, property held for investment). Further, this discussion does not purport to consider all aspects of U.S. federal income taxation that may be relevant to a particular shareholder in light of such shareholder’s particular circumstances, or that may apply to shareholders subject to special treatment under the U.S. federal income tax laws (including, for example, insurance companies, dealers or brokers in securities or foreign currencies, traders in securities who elect the mark-to-market method of accounting, U.S. Holders (as defined below) that have a functional currency other than the U.S. dollar, persons who are required to recognize income or gain with respect to their shares of our common stock or preferred stock, as applicable, no later than such income or gain is required to be reported on an applicable financial statement, holders subject to any alternative minimum tax, tax-exempt organizations, retirement plans, individual retirement accounts or other tax-deferred or advantaged accounts (or persons holding common stock or preferred stock through such plans or accounts), cooperatives, banks and other financial institutions, real estate investment trusts, regulated investment companies, certain former citizens or former long-term residents of the United States, controlled foreign corporations, passive foreign investment companies, expatriated entities, entities all of the interests in which are held by a “qualified foreign pension funds” (within the meaning of section 897(l)(2) of the Code), partnerships (including entities or arrangements classified as partnerships for U.S. federal income tax purposes), S corporations, or other pass-through entities or investors in partnerships (including entities or arrangements classified as partnerships for U.S. federal income tax purposes) or such other entities, holders who hold shares of our common stock or preferred stock as part of a hedge, straddle, constructive sale, conversion or other integrated or risk reduction transaction, holders who acquired their shares of common stock through the exercise of employee stock options or other compensation arrangements and holders of dissenting shares). Moreover, this discussion does not address the tax consequences of the Merger or the redemption of our preferred stock arising under any applicable state, local or foreign tax laws or the application of other U.S. federal taxes, such as the federal estate tax, the federal gift tax, the “Medicare” tax on certain net investment income, the alternative minimum tax or any withholding considerations under FATCA (defined for this purpose as sections 1471 through 1474 of the Code, the Treasury Regulations and administrative guidance thereunder and the intergovernmental agreements entered into, and laws and regulations promulgated, pursuant thereto or in connection therewith). This discussion also does not address the tax consequences to any shareholder that contributes any shares to 365 or any of its affiliates as part of the “rollover” prior to the effective time of the Merger, or that will otherwise own (actually or constructively) an interest in 365 or any of its affiliates.

If a partnership (including for this purpose any entity or arrangement treated as a partnership for U.S. federal income tax purposes) holds shares of our common stock or preferred stock, the tax treatment of a partner in such partnership will generally depend on the status of the partners and the activities of the partnership. If you are a partner of a partnership holding shares of our common stock or preferred stock, you should consult your tax advisor.

Holders of our common stock or preferred stock are urged to consult their own tax advisors regarding the application of the U.S. federal tax laws to their particular situation and the applicability and effect of state, local or foreign tax laws and tax treaties.

For purposes of this discussion, the term “U.S. Holder” means a beneficial owner of our common stock or preferred stock that is for U.S. federal income tax purposes:

For purposes of this discussion, the term “Non-U.S. Holder” means a beneficial owner of our common stock or preferred stock that is not a U.S. Holder and is not an entity or arrangement classified as a partnership for U.S. federal income tax purposes.

The receipt of cash by U.S. Holders in exchange for shares of our common stock pursuant to the Merger, and the receipt of the preferred stock redemption payment by U.S. Holders pursuant to the redemption of our preferred stock, in each case, will be a taxable transaction for U.S. federal income tax purposes. In general, a U.S. Holder who receives cash in exchange for shares of our common stock pursuant to the Merger or pursuant to the redemption of our preferred stock, in each case, will recognize gain or loss in an amount equal to the difference, if any, between (i) the amount of cash received and (ii) the U.S. Holder’s adjusted tax basis in such shares of our common stock or preferred stock, as applicable.

Any such gain or loss recognized by a U.S. Holder upon the exchange of shares of our common stock pursuant to the Merger or pursuant to the redemption of our preferred stock, in each case, generally will be capital gain or loss and will be long-term capital gain or loss if the U.S. Holder’s holding period in its shares of common stock or preferred stock, as applicable, is more than one year on the closing date of the Merger. Long-term capital gains of non-corporate U.S. Holders generally are eligible for preferential U.S. federal income tax rates under current law. The deductibility of capital losses is subject to limitations. If a U.S. Holder acquired different blocks of our common stock or preferred stock at different times or different prices, such U.S. Holder must determine its adjusted tax basis and holding period separately with respect to each block of stock.

Payments made in exchange for shares of our common stock pursuant to the Merger or for shares of our preferred stock pursuant to the redemption of our preferred stock may be subject, under certain circumstances, to information reporting and backup withholding (currently at a rate of 24%). To avoid backup withholding, a U.S. Holder that does not otherwise establish an exemption should complete and return IRS Form W-9, certifying that such U.S. Holder is a U.S. person, the taxpayer identification number provided is correct and such U.S. Holder is not subject to backup withholding. Backup withholding is not an additional tax. Any amounts withheld under the backup withholding rules may be refunded or credited against a U.S. Holder’s U.S. federal income tax liability, if any, provided that such U.S. Holder furnishes the required information to the IRS in a timely manner.

A Non-U.S. Holder generally will not be subject to U.S. federal income tax on any gain realized on the receipt of cash in exchange for shares of our common stock in the Merger, or the receipt of the preferred stock redemption payment pursuant to the redemption of our preferred stock, unless:

Gain described in the first bullet point above will generally be subject to U.S. federal income tax on a net income basis at the regular graduated U.S. federal income tax rates in the same manner as if such Non-U.S. Holder were a U.S. Holder. A Non-U.S. Holder that is a corporation also may be subject to a branch profits tax at a rate of 30% (or such lower rate as may be specified under an applicable income tax treaty) on such gain, subject to certain adjustments.

Gain described in the second bullet point above will generally be subject to U.S. federal income tax at a rate of 30% (or such lower rate as may be specified under an applicable income tax treaty), which may be offset by U.S.-source capital losses of the Non-U.S. Holder (even though the individual is not considered a resident of the United States), provided the Non-U.S. Holder has timely filed U.S. federal income tax returns with respect to such losses.

With respect to the third bullet point above, we believe that we are not currently, and have not been during the preceding five years, a USRPHC. Even if we are (or have been during the applicable period) a USRPHC, gain arising from the sale or other taxable disposition of our common stock or preferred stock by a Non-U.S. Holder will not be subject to U.S. federal income tax, provided that, (i) in the case of our common stock, (x) our common stock is regularly traded on an established securities market (within the meaning of applicable Treasury Regulations) and such Non-U.S. Holder owned, actually and constructively, 5% or less of our common stock throughout the shorter of the five-year period ending on the date of the Merger or the Non-U.S. Holder’s holding period or, (y) if our common stock is not regularly traded on an established securities market (within the meaning of applicable Treasury Regulations), our preferred stock is regularly traded on an established securities market (within the meaning of applicable Treasury Regulations) and on the date such Non-U.S. Holder acquired its interest in (or acquired additional interests in) such common stock, such Non-U.S. Holder’s common stock (taking into account actual and constructive ownership) had a fair market value not greater than the fair market value on that date of 5% of our preferred stock, and, (ii) in the case of our preferred stock, (x) our preferred stock is regularly traded on an established securities market (within the meaning of applicable Treasury Regulations) and such Non-U.S. Holder owned, actually and constructively, 5% or less of our preferred stock throughout the shorter of the five-year period ending on the date of the redemption or the Non-U.S. Holder’s holding period or, (y) if our preferred stock is not regularly traded on an established securities market (within the meaning of applicable Treasury Regulations), our common stock is regularly traded on an established securities market (within the meaning of applicable Treasury Regulations) and on the date such Non-U.S. Holder acquired its interest in (or acquired additional interests in) such preferred stock, such Non-U.S. Holder’s preferred stock (taking into account actual and constructive ownership) had a fair market value not greater than the fair market value on that date of 5% of our common stock. Non-U.S. Holders are urged to consult their tax advisors about the consequences that could result if we are, were or were to become a USRPHC.

Payments made to a Non-U.S. Holder in exchange for shares of our common stock pursuant to the Merger, and payments made to a Non-U.S. Holder in redemption of our preferred stock, may be subject to information reporting to the IRS and backup withholding (currently at a rate of 24%). A Non-U.S. Holder generally can avoid information reporting and backup withholding by providing the Paying Agent with the applicable and properly completed and executed IRS Form W-8 certifying the holder’s non-U.S. status or by otherwise establishing an exemption. Copies of information returns that are filed with the IRS may be made available under an applicable tax treaty or information exchange agreement to the tax authorities of the country in which the Non-U.S. Holder resides or is established.

Backup withholding is not an additional tax. Any amounts withheld under the backup withholding rules may be refunded or credited against a Non-U.S. Holder’s U.S. federal income tax liability, if any, provided that such Non-U.S. Holder furnishes the required information to the IRS in a timely manner.

This summary of the material U.S. federal income tax consequences of the Merger and the redemption of our preferred stock to U.S. Holders and Non-U.S. Holders is for general information purposes only and is not tax advice. Holders of our common stock and preferred stock should consult their own tax advisors regarding the application of the U.S. federal tax laws to their particular situation and the applicability and effect of state, local or foreign tax laws and tax treaties.

The following summary describes certain relevant provisions of the Voting Agreement entered into by each of our directors and Hudson. The descriptions of the Voting Agreements in this summary and elsewhere in this proxy statement are not complete and are qualified in their entirety by reference to the Voting Agreements. A copy of the voting agreement entered into by Hudson is attached to this proxy statement as Annex C and a copy of the form of voting agreement entered into by each of our directors is attached to this proxy statement as Annex D, which are incorporated into this proxy statement by reference. We encourage you to read the Voting Agreement carefully and in its entirety because this summary may not contain all the information about the Voting Agreement that is important to you. The rights and obligations of the parties are governed by the express terms of the Voting Agreement and not by this summary or any other information contained in this proxy statement.

Under the Voting Agreement, each of the Supporting Shareholders, among other things and subject to the terms and conditions of the respective Voting Agreement, agreed to vote its shares of Cantaloupe stock (including all Cantaloupe equity awards) owned as of June 15, 2025, and all additional shares of Cantaloupe stock (including all

Cantaloupe equity awards and other rights to acquire Cantaloupe stock) of which it acquired record or beneficial ownership following the date of its Voting Agreement until the Support Expiration Date (which we refer to as the “Subject Securities”), (a) vote in favor of (i) the proposals set forth in this proxy statement and (ii) each of the other actions contemplated by the Merger Agreement, (b) vote against any action or agreement that would result in a breach of any representation, warranty, covenant or obligation of Cantaloupe in the Merger Agreement and (c) vote against the following actions (other than all actions and transactions contemplated by the Merger Agreement, including the Merger, and the Voting Agreement): (i) any change in the Board; (ii) any action or proposal to amend, or waive any provision of the Cantaloupe Articles or the Cantaloupe Bylaws; (iii) any Acquisition Proposal or any agreement related thereto, and any action in furtherance of any Acquisition Proposal and (iv) any other action which is intended, or would reasonably be expected, to result in any of the conditions to the consummation of the Merger under the Merger Agreement not being fulfilled.

Each Voting Agreement will automatically terminate and become void and of no further force or effect at the earliest of: (a) the effective time of the Merger; (b) the date on which the Merger Agreement is validly terminated in accordance with its terms; and (c) the date of any modification, waiver or amendment to any provision of the Merger Agreement effected without such Supporting Shareholder’s consent that (i) decreases the amount or changes the form of merger consideration, (ii) extends the End Date or (iii) imposes any additional conditions on the consummation of the Merger.

Pursuant to the Voting Agreements, each of the Supporting Shareholders will not (and will not permit any person under such Supporting Shareholder’s control to), without the prior written consent of 365, directly or indirectly: (i) grant or permit the grant of any proxies, powers of attorney, rights of first offer or refusal or other authorizations in or with respect to, or enter into any voting trust or voting agreement or arrangement with respect to, any Subject Securities or any interest therein; (ii) sell (including short sell), assign, transfer, tender, pledge, encumber, grant a participation interest in, hypothecate or otherwise dispose of (including by gift) (which we refer to as a “Transfer”), any Subject Securities or any interest therein; (iii) create or otherwise permit any lien or other restriction to be created on any Subject Securities (other than permitted liens); (iv) enforce or permit the execution of the provisions of any redemption, share purchase or sale, recapitalization or other agreement with Cantaloupe or any other person, with respect to any Subject Securities or any interest therein (other than, if applicable, the Redemption); (v) enter into any agreement with any person with respect to the direct or indirect Transfer of any Subject Securities or any interest therein; (vi) enter into a swap or other agreement or any transaction that Transfers, in whole or in part, the economic consequence of ownership of any Subject Securities; or (vii) agree to do or any of the foregoing. Each of the Supporting Shareholders will not, and will not permit any person under such Supporting Shareholder’s control or any of their respective representatives acting on its behalf to, seek or solicit any such Transfer or any such agreement. Without limiting the generality of the foregoing, each of the Supporting Shareholders will not tender, agree to tender or cause or permit to be tendered any Subject Securities into or otherwise in connection with any tender or exchange offer.

Notwithstanding the foregoing, each of the Supporting Shareholders may Transfer Subject Securities: (a) if such Supporting Shareholder is an individual, (i) to any member of such Supporting Shareholder’s immediate family, (ii) upon the death of such Supporting Shareholder, (iii) to any trust for the direct or indirect benefit of such Supporting Shareholder or the immediate family of such Supporting Shareholder for bona fide estate planning purposes or (iv) to a partnership, limited liability company or other entity of which such Supporting Shareholder and/or the immediate family of such Supporting Shareholder are the legal and beneficial owners of all the outstanding equity securities or similar interests; or (b) if such Supporting Shareholder is a corporation, partnership, trust, limited liability company or other business entity, (x) to another corporation, partnership, trust, limited liability company or other business entity that is an affiliate controlled by such Supporting Shareholder, (y) to one or more partners or members of such Supporting Shareholder or to an affiliate under common control with such Supporting Shareholder or (z) to any investment fund or other entity controlling, controlled by, managing or managed by or under common control with such Supporting Shareholder or affiliates of such Supporting Shareholder (including, for the avoidance of doubt, where such Supporting Shareholder is a partnership, to its general partner or a successor partnership or fund, or any other funds managed by such partnership); provided, however, that a Transfer referred to in this sentence will be permitted only if, as a precondition to such Transfer, the transferee agrees in a written document, reasonably satisfactory in form and substance to 365, to be bound by all of the terms of the Voting Agreement.

Cantaloupe has agreed to reimburse Hudson and its directors, officers, employees and agents acting on Hudson’s behalf for out-of-pocket expenses incurred by them, as such expenses are incurred, whether such expenses were incurred prior to or after June 15, 2025, in connection with the negotiation, execution and performance of the Voting Agreement and any claims arising out of, related to or involving the Voting Agreement (including without limitation, reasonable fees and expenses of counsel), in each case except in the case of willful and material breach by Hudson or such representatives.

The summary of the material provisions of the Merger Agreement set forth below and elsewhere in this proxy statement is qualified in its entirety by reference to the Merger Agreement, a copy of which is attached to this proxy statement as Annex A, and incorporated into this proxy statement by reference. This summary does not purport to be complete and may not contain all of the information about the Merger Agreement that is important to you. We encourage you to read the Merger Agreement carefully and in its entirety. The rights and obligations of the parties are governed by the express terms of the Merger Agreement and not by this summary or any other information contained in this proxy statement.

The Merger Agreement is described in this proxy statement and included as Annex A only to provide investors and security holders with information regarding its terms and conditions and is not intended to provide any factual information about Cantaloupe, 365, Holdco, Holdco II or Merger Subsidiary or their respective businesses. Accordingly, the representations, warranties, covenants and other agreements in the Merger Agreement should not be read alone. Such information can be found elsewhere in this proxy statement or, in the case of Cantaloupe, in the public filings that Cantaloupe makes with the SEC, which are available without charge through the SEC’s website at www.sec.gov. See the section of this proxy statement titled “Where Shareholders Can Find More Information”.

The representations, warranties, covenants and other agreements in the Merger Agreement and described below were made only for the purposes of the Merger Agreement and solely for the benefit of the parties to the Merger Agreement as of specific dates. Such representations, warranties, covenants and other agreements were negotiated with the principal purposes of establishing the circumstances in which a party to the Merger Agreement may have the right not to close the Merger. Such representations, warranties, covenants and other agreements may have also been made for the purposes of allocating contractual risk between the parties to the Merger Agreement instead of establishing these matters as facts, may or may not be accurate as of any specific date, may be subject to important limitations and qualifications (including exceptions thereto set forth in the disclosure letter agreed to by the contracting parties (which we refer to as the “Company Disclosure Letter”)) and may therefore not be complete. The representations, warranties, covenants and other agreements in the Merger Agreement may also be subject to a contractual standard of materiality applicable to the contracting parties that may differ from those applicable to shareholders and reports and documents filed with the SEC, and in some cases were qualified by the Company Disclosure Letter, which such disclosures are not reflected in the text of the Merger Agreement. Investors should not rely on the representations, warranties, covenants and other agreements or any descriptions thereof as characterizations of the actual state of facts or condition of the parties to the Merger Agreement or any of their respective subsidiaries or affiliates. Moreover, information concerning the subject matter of the representations and warranties, which do not purport to be accurate as of the date of this proxy statement, may have changed since the date of the Merger Agreement, and subsequent developments or new information qualifying a representation and warranty may not have been included in this proxy statement.

At the effective time of the Merger, on the terms and subject to the conditions of the Merger Agreement, Merger Subsidiary will merge with and into Cantaloupe, with Cantaloupe surviving the Merger as a wholly owned subsidiary of Holdco II. The Cantaloupe Articles and the Cantaloupe Bylaws as in effect immediately prior to the effective time of the Merger will be the articles of incorporation and bylaws of the surviving corporation until thereafter amended as provided therein or in accordance with applicable law.

The closing of the Merger will occur at 8:00 a.m., Eastern time, as soon as possible, but in any event no later than five business days following the date the conditions set forth in the Merger Agreement (other than those conditions that by their nature are to be satisfied at the closing, but subject to the satisfaction or, to the extent permissible, waiver of those conditions at the closing) have been satisfied or, to the extent permissible, waived, or at such other time or on such other date as Cantaloupe and 365 may mutually agree in writing.

On the closing date, the parties to the Merger Agreement will cause (i) a statement of merger in such form as required by the PBCL to be properly executed and filed with the Department of State of the Commonwealth of Pennsylvania and (ii) a certificate of merger in such form as required by the DGCL relating to the Merger to be properly executed

and filed with the Secretary of State of the State of Delaware, and will make all other filings or recordings required by applicable law. The Merger will become effective at such time agreed to by the parties to the Merger Agreement, which will be as soon as practicable following the filing of both of the statement of merger and the certificate of merger and will be expressly stated in such filings, or at such later time that the parties to the Merger Agreement may agree and designate in the statement of merger and certificate of merger as the effective time of the Merger.

At the effective time of the Merger, each share of our common stock issued and outstanding immediately prior to the effective time of the Merger, but excluding the shares of common stock described in the following paragraph and the rollover shares (if any), will be converted into the right to receive $11.20 in cash, without interest and less any applicable withholding taxes.

At the effective time of the Merger, each share of Cantaloupe stock owned by Cantaloupe or any subsidiary of Cantaloupe as treasury stock (including all shares of preferred stock redeemed by Cantaloupe in accordance with the Merger Agreement) or owned by 365, Holdco, Holdco II or Merger Subsidiary, or by any other subsidiary of 365, immediately prior to the effective time of the Merger, will be canceled without payment.

Each rollover share (if any) will not be entitled to receive the merger consideration and will, (i) immediately prior to the effective time of the Merger, be subject to the treatment specified under the rollover agreement applicable to such rollover shares and (ii) at the effective time of the Merger, be canceled and retired and will cease to exist, and no consideration will be delivered in exchange for such cancellation and retirement. As of the date of this proxy statement, Douglas G. Bergeron, Chairman of the Board, has had preliminary discussions with representatives of 365 regarding a potential rollover arrangement with respect to shares of Cantaloupe’s common stock held by Mr. Bergeron, but, as of the date of this proxy statement, there is no understanding as to the amount of shares of Cantaloupe’s common stock that would be subject to such rollover arrangement, and no definitive agreement has been entered into between Mr. Bergeron and 365 or its affiliates regarding such potential rollover. Other than as described above, none of 365, Holdco, Holdco II, Merger Subsidiary or any of their respective affiliates has entered into any agreements, arrangements or understandings with respect to rollover shares.

For more information, see the sections of this proxy statement titled “The Merger—Effects of the Merger” and “The Merger—Interests of Certain Persons in the Merger—Employment Discussions; Rollover Agreements”.

At the effective time of the Merger, each share of common stock, par value $0.01 per share, of Merger Subsidiary issued and outstanding immediately prior to the effective time of the Merger will be converted into and become one newly issued, fully paid and non-assessable share of common stock, par value $0.01 per share, of the surviving corporation.

At or immediately prior to the effective time of the Merger, each Cantaloupe RSU that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe RSU, become fully vested and free of restrictions and will be canceled and converted into the right to receive, in accordance with the terms of the Merger Agreement, an amount in cash equal to the merger consideration.

At or immediately prior to the effective time of the Merger, each Cantaloupe PSU that is outstanding immediately prior to the effective time of the Merger which remains subject to vesting based on achieving certain performance metrics will, automatically and without any action required on the part of the holder of such Cantaloupe PSU, become vested with respect to that number of shares of common stock based on deemed achievement of the performance metrics at target performance. Immediately thereafter, Cantaloupe PSUs will be canceled and converted into the right to receive, with respect to each such vested share of common stock underlying such Cantaloupe PSU, in accordance with the terms of the Merger Agreement, an amount in cash equal to the merger consideration.

At or immediately prior to the effective time of the Merger, each Cantaloupe Restricted Stock Award that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe Restricted Stock Award, become fully vested and free of restrictions and will be canceled and converted into the right to receive, in accordance with the terms of the Merger Agreement, an amount in cash equal to the merger consideration.

At or immediately prior to the effective time of the Merger, each In-the-Money Option that is outstanding immediately prior to the effective time of the Merger will, automatically and without any action required on the part of the holder of such Cantaloupe Option, become fully vested and free of restrictions and be canceled in exchange for cash in an amount equal to (i) the total number of shares of common stock for which such Cantaloupe Option is exercisable, multiplied by (ii) the excess of the merger consideration over the per share exercise price of such Cantaloupe Option. At the effective time of the Merger, each Out-of-the-Money Option that is outstanding immediately prior to the effective time of the Merger will be canceled without consideration and will be of no further force and effect.

Prior to the effective time of the Merger, 365 must appoint an agent reasonably acceptable to Cantaloupe (which we refer to as the “Paying Agent”) for the purpose of paying the merger consideration in respect of (i) Certificates or (ii) Uncertificated Shares. Promptly after the effective time of the Merger (and after receipt by the Paying Agent from Cantaloupe’s transfer agent of all information reasonably necessary to enable the Paying Agent to effect the mailing; provided that 365 and the surviving corporation will use reasonable best efforts to obtain such information to enable such mailing to occur no later than the fifth business day following the effective time of the Merger), 365 must send, or cause the Paying Agent to send, to each holder of record of shares of common stock at the effective time of the Merger a letter of transmittal (in a form that was reasonably acceptable to Cantaloupe prior to the effective time of the Merger) and instructions (which will specify that the delivery will be effected, and risk of loss and title will pass, only upon proper delivery of the Certificates or transfer of the Uncertificated Shares to the Paying Agent) for use in such exchange.

Each holder of shares of common stock that have been converted into the right to receive the merger consideration will be entitled to receive, upon (i) surrender to the Paying Agent of a Certificate, together with a properly completed letter of transmittal (or affidavit in lieu of lost, stolen or destroyed Certificates), or (ii) receipt of an “agent’s message” by the Paying Agent (or such other evidence, if any, of transfer that the Paying Agent may reasonably request) in the case of a book-entry transfer of Uncertificated Shares, the merger consideration in respect of each share of common stock represented by a Certificate or Uncertificated Share. Until so surrendered or transferred, as the case may be, each such Certificate or Uncertificated Share will represent after the effective time of the Merger for all purposes only the right to receive the merger consideration, without interest thereon.

If any Certificate representing common stock has been lost, stolen or destroyed, upon the making of an affidavit of that fact by the person claiming such Certificate to be lost, stolen or destroyed and, if required by the surviving corporation, the posting by such person of a bond, in such reasonable amount as the surviving corporation may direct, as indemnity against any claim that may be made against it with respect to such Certificate, the Paying Agent will issue, in exchange for such lost, stolen or destroyed Certificate, the merger consideration to be paid in respect of the shares of common stock represented by such Certificate, as contemplated in the Merger Agreement.

At or prior to the effective time of the Merger, 365 must deposit, or cause to be deposited, with the Paying Agent, for the benefit of the holders of common stock, the Payment Fund. The Payment Fund will, pending its disbursement to the holders of common stock, be invested by the Paying Agent as directed by 365 or the surviving corporation in certain short-term obligations set forth in the Merger Agreement; provided that no such investment or losses will affect the amounts payable to the holders of common stock and 365 will promptly replace or cause to be replaced any lost funds deposited with the Paying Agent that are lost through any investment, or otherwise deposit funds to the Payment Fund so as to ensure that the Payment Fund is at all times maintained at a level sufficient for the Paying Agent to pay the aggregate merger consideration. Earnings from investments, subject to the immediately preceding proviso, will be paid to and will be the sole and exclusive property of 365 and the surviving corporation.

Cantaloupe, on the one hand, and 365, Holdco, Holdco II and Merger Subsidiary, on the other hand, have each made representations and warranties in the Merger Agreement.

The representations and warranties contained in the Merger Agreement will not survive the effective time of the Merger.

Cantaloupe has made customary representations and warranties to 365, Holdco, Holdco II and Merger Subsidiary in the Merger Agreement regarding aspects of Cantaloupe’s business and various other matters pertinent to the Merger, which are subject, in some cases, to specified exceptions and qualifications contained in the Merger Agreement. Some of the representations and warranties in the Merger Agreement made by Cantaloupe are qualified by “materiality” or “Material Adverse Effect” standards. For purposes of the Merger Agreement, “Material Adverse Effect” means, with respect to Cantaloupe or any of its subsidiaries, any change, effect, event, circumstance, development, condition or occurrence that has, or would reasonably be expected to have, a material adverse effect on the financial condition, business, assets or results of operations of Cantaloupe and its subsidiaries, taken as a whole, excluding any change, effect, event, circumstance, development, condition or occurrence resulting from or arising in connection with:

provided, however, that in the case of circumstances described in the first six bullets, any change, effect, event, circumstance, development, condition or occurrence may be taken into account in determining whether or not there has been a Material Adverse Effect only to the extent any such change, effect, event, circumstance, development, condition or occurrence has a disproportionate adverse impact on Cantaloupe and its subsidiaries, taken as a whole, as compared to other companies of a similar size operating in the industry in which Cantaloupe operates, in which case only the incremental disproportionate adverse impact on Cantaloupe and its subsidiaries may be taken into account in determining whether there has been a Material Adverse Effect.

The topics covered by Cantaloupe’s representations and warranties relate to, among other things, the following:

365, Holdco, Holdco II and Merger Subsidiary have made customary representations and warranties to Cantaloupe in the Merger Agreement regarding themselves and matters pertinent to the Merger, which are subject, in some cases, to specified exceptions and qualifications contained in the Merger Agreement.

The topics covered by 365’s, Holdco’s, Holdco II’s and Merger Subsidiary’s representations and warranties include the following:

Cantaloupe has agreed to certain covenants in the Merger Agreement restricting the conduct of its business between the date of the Merger Agreement and the effective time of the Merger or, if applicable, the date on which the Merger Agreement is terminated. In general, Cantaloupe has agreed that, except for matters set forth in the Company Disclosure Letter, as expressly contemplated by the Merger Agreement, as required by applicable law or with the prior written consent of 365, from and after the date of the Merger Agreement until the effective time of the Merger, Cantaloupe will, and will cause each of its subsidiaries to, use commercially reasonable efforts to conduct its business in the ordinary course consistent with past practice in all material respects and to preserve intact its present business organization in all material respects, keep available the services of its directors, officers and key employees and maintain satisfactory relationships with its customers, lenders, suppliers and others having material business relationships with it. No action by Cantaloupe or any of its subsidiaries with respect to the matters specifically addressed below will be deemed to be a breach of the covenant described in this paragraph unless such action would constitute a breach of the restrictions described below.

Without limiting the generality of the preceding paragraph, Cantaloupe has agreed that, except for matters set forth in the corresponding section of the Company Disclosure Letter, as expressly contemplated by the Merger Agreement, as required by applicable law or with the prior written consent of 365, between the date of the Merger Agreement and the effective time of the Merger, Cantaloupe will not and will not permit any of its subsidiaries to:

Except as expressly permitted by the Merger Agreement, Cantaloupe has agreed that it nor any of its subsidiaries or any of their respective officers, directors or financial advisors will, and it and its subsidiaries will use its reasonable efforts to cause its and their other representatives not to, directly or indirectly:

provided that, notwithstanding the foregoing or anything to the contrary in the Merger Agreement, Cantaloupe and its subsidiaries and its and their representatives will enforce, and will not be permitted to waive, terminate or modify, any standstill provisions in any agreement with any third party to the extent such standstill provisions would prohibit such third party from making an Acquisition Proposal to the Board (or any committee thereof), unless (i) if requested by a person party to such standstill solely to permit the applicable person to make, on a confidential basis to the Board, an Acquisition Proposal conditioned upon such person agreeing to compliance by Cantaloupe with this paragraph, the Board has determined in good faith, after consultation with its outside legal counsel, that the failure to take such action would be inconsistent with the directors’ fiduciary duties under applicable law and (ii) if such determination in clause (i) is made, Cantaloupe provides prompt written notice to 365 of the taking of such action. Without limiting the foregoing, it is understood that any action taken by any of Cantaloupe’s subsidiaries or representatives that would constitute a breach of this paragraph if taken by Cantaloupe, will constitute a breach by Cantaloupe of this paragraph. Notwithstanding anything to the contrary contained in this paragraph, Cantaloupe and its representatives may direct any third party that has made Acquisition Proposal or an Inquiry to the restrictions set forth in Section 6.03 of the Merger Agreement.

Notwithstanding the foregoing, if at any time prior to obtaining the required Cantaloupe shareholder approval, Cantaloupe receives an unsolicited, bona fide written Acquisition Proposal made after the date of the Merger Agreement (and not withdrawn) from a third party that has not resulted from a material breach of Section 6.03 of the Merger Agreement, the Board may, prior to obtaining the required Cantaloupe shareholder approval and subject to compliance with this paragraph:

Cantaloupe is required to promptly notify 365 (but in no event later than 24 hours) after receipt by Cantaloupe (or any of its representatives) of (i) any Acquisition Proposal made after the date of the Merger Agreement and (ii) any written request made after the date of the Merger Agreement for information relating to Cantaloupe or any of its subsidiaries or for access to the business, properties, assets, books or records of Cantaloupe or any of its subsidiaries by any third party in connection with, or that, to the knowledge of Cantaloupe or any member of the Board, is considering making, or is reasonably likely to make after the date of the Merger Agreement, an Acquisition Proposal, which written notice will identify the relevant third party and, to the extent known or available, the material terms and conditions of, any such Acquisition Proposal (including any material changes or proposed changes thereto) and include copies of any proposed agreements, material documentation and other written materials, including relating to the financing thereof. Thereafter, Cantaloupe will keep 365 reasonably informed, on a reasonably prompt and

timely basis (but in no event later than 24 hours following receipt of applicable details by Cantaloupe), of the status and details of any such Acquisition Proposal (including any changes or proposed thereto), including providing copies of any revised agreements, written documentation or materials relating to such Acquisition Proposal, including relating to the financing thereof.

The Board will not:

Notwithstanding anything to the contrary set forth in the Merger Agreement, prior to obtaining the required Cantaloupe shareholder approval, the Board may, in response to a Superior Proposal, (i) make an Adverse Recommendation Change and/or (ii) terminate the Merger Agreement to concurrently enter into a definitive agreement with respect to such Superior Proposal in accordance with the termination rights of Cantaloupe set forth in the Merger Agreement, if, and only if:

After delivery of any written notice pursuant to ‎the foregoing, and until the valid termination of the Merger Agreement in accordance with its terms, Cantaloupe will promptly keep 365 informed of all material developments affecting the material terms of any such Superior Proposal.

Notwithstanding anything to the contrary set forth in the Merger Agreement, prior to obtaining the required Cantaloupe shareholder approval, the Board may, in response to an Intervening Event, make an Adverse Recommendation Change; provided, however, that the Board will not be entitled to effect such an Adverse Recommendation Change until:

Cantaloupe, its subsidiaries and their respective officers, directors and financial advisors will, and Cantaloupe and its subsidiaries will cause their other representatives engaged in connection with the transactions contemplated in the Merger Agreement to, cease immediately and cause to be terminated any and all existing activities, solicitations, discussions or negotiations, if any, with any third party conducted prior to the date of the Merger Agreement with respect to any Acquisition Proposal or Inquiry. Cantaloupe will immediately terminate access by any third party to any data room and promptly request each third party that has executed a confidentiality agreement prior to the date of the Merger Agreement in connection with its consideration of acquiring Cantaloupe or any of its subsidiaries to return or destroy (as provided in the terms of such confidentiality agreement) all confidential information furnished to such third party prior to the date of the Merger Agreement by or on behalf of it or any of its subsidiaries.

Nothing contained in Section 6.03 of the Merger Agreement will prohibit Cantaloupe or the Board from (i) taking and disclosing to the shareholders of Cantaloupe a position contemplated by Rule 14e-2(a) or Rule 14d-9 promulgated under the Exchange Act (or any similar communication to the shareholders of Cantaloupe in connection with the making or amendment of a tender offer or exchange offer), (ii) making any disclosure to the shareholders of Cantaloupe that is required by applicable law or Nasdaq or (iii) making any “stop, look and listen” communication to the shareholders of Cantaloupe pursuant to Rule 14d-9(f) under the Exchange Act, including, in each case, such disclosures that contain a factually accurate statement by Cantaloupe or the Board (or a committee thereof) that states that Cantaloupe has received an Acquisition Proposal, the identity of the person making such Acquisition Proposal, the material terms of such Acquisition Proposal and the provisions of the Merger Agreement applicable with respect thereto; provided, however, that any such disclosure will constitute an Adverse Recommendation Change if the Board fails to expressly and publicly reaffirm the Board recommendation in such public disclosure.

For the purposes of the Merger Agreement, an “Acquisition Proposal” means, other than the transactions contemplated by the Merger Agreement, any bona fide offer or proposal of any third party relating to (a) any acquisition or purchase (including through any sale, lease, exchange, license, transfer, mortgage, pledge or disposition), direct or indirect, of assets (including equity securities of a subsidiary of Cantaloupe) having a fair market value (as determined in good faith by the Board) equal to 15% or more of the fair market value (as determined in good faith by the Board) of the consolidated assets of Cantaloupe, or to which 15% or more of the consolidated revenues or earnings of Cantaloupe are attributable, or of 15% or more of any class of equity or voting securities of Cantaloupe, (b) any takeover offer, tender offer or exchange offer or other similar transaction that, if consummated, would result in such third party beneficially owning 15% or more of any class of equity or voting securities of Cantaloupe, (c) a merger, consolidation, business combination, liquidation, dissolution, amalgamation, share exchange, joint venture, partnership, recapitalization, reorganization or other similar transaction (i) involving Cantaloupe or any of its subsidiaries whose assets, individually or in the aggregate, have a fair market value (as determined in good faith by the Board) equal to 15% or more of the fair market value (as determined in good faith by the Board) of the consolidated assets of Cantaloupe, or to which 15% or more of the consolidated revenues or earnings of Cantaloupe, are attributable or (ii) pursuant to which the shareholders of Cantaloupe immediately prior to the consummation of such transaction would, as a result of such transaction, hold less than 85% of the equity or voting securities of Cantaloupe, or (d) any combination of the foregoing.

For the purposes of the Merger Agreement, a “Superior Proposal” means a bona fide, unsolicited written Acquisition Proposal (with references to “15% or more” and “85%” being deemed to be replaced with a reference to “a

majority”) by a third party, which did not result from or arise out of a material breach of Section 6.03 of the Merger Agreement, and which the Board determines in good faith after consultation with Cantaloupe’s outside legal and financial advisors to be more favorable to Cantaloupe and its shareholders from a financial point of view than the Merger, taking into account all financial, legal, financing (including availability thereof), regulatory and other aspects of such proposal, and risks, likelihood and timing of consummation of such proposal, such other matters that the Board deems relevant and any changes to the terms of the Merger Agreement proposed by 365 in response to such Superior Proposal.

For the purposes of the Merger Agreement, an “Intervening Event” means an event, fact, circumstance, development or occurrence, in each case, that is material to Cantaloupe and its subsidiaries, taken as a whole, that (i) is not known to or reasonably foreseeable by the Board as of the date of the Merger Agreement, (ii) first becomes known to or by the Board prior to obtaining the required Cantaloupe shareholder approval and (iii) does not relate to an Acquisition Proposal or any matter relating thereto or consequence thereof; provided that changes in the market price or trading volume of the shares of Cantaloupe stock or the fact that Cantaloupe meets or exceeds internal or published projections, budgets, forecasts or estimates of revenues, earnings or other financial metrics will not constitute, or be considered in determining whether there has been, an Intervening Event (but any underlying causes of such changes or facts may constitute, or be taken into account in determining whether there has been, an Intervening Event).

Commencing upon the initial submission to the SEC of the preliminary proxy statement, Cantaloupe will, on a bi-weekly basis, run a broker search for a deemed record date of 20 business days after the date of such search. Promptly following clearance of the proxy statement by the SEC, Cantaloupe will (i) by resolutions of the Board, establish the earliest practicable record date for the Special Meeting, (ii) by resolutions of the Board, establish the earliest practicable date for a special meeting of its shareholders for the purpose of voting on the adoption of the Merger Agreement in accordance with Cantaloupe’s organizational documents and applicable law and (iii) solicit proxies to obtain the required Cantaloupe shareholder approval. In connection therewith, the Board will duly call, give notice of, convene and hold the Special Meeting within 40 days after the definitive proxy statement is mailed to shareholders of Cantaloupe.

Notwithstanding the immediately preceding sentence, Cantaloupe may adjourn or postpone the Special Meeting after consultation with 365, and if requested by 365 in writing, will adjourn or postpone the Special Meeting in compliance with applicable law (i) to the extent necessary to ensure that any supplement or amendment to the proxy statement that is required by applicable law is provided to Cantaloupe shareholders, (ii) if, as of the time for which the Special Meeting is scheduled as set forth in the proxy statement, there are an insufficient number of shares of Cantaloupe stock present or represented by proxy at the Special Meeting to constitute a quorum at such meeting, but only until there are a sufficient number of shares of Cantaloupe stock present or represented by proxy at the Special Meeting to obtain such a quorum or (iii) if as of the time for which the Special Meeting is scheduled as set forth in the proxy statement, there are insufficient shares of Cantaloupe stock represented (in person or by proxy) to obtain the required Cantaloupe shareholder approval, but only until there are a sufficient number of shares of common and preferred stock present or represented by proxy at the Special Meeting to obtain the required Cantaloupe shareholder approval; provided that the Special Meeting will not be adjourned or postponed pursuant to the foregoing clauses (ii) or (iii) to a date that is more than 15 days after the date on which the Special Meeting was originally scheduled without the prior written consent of 365 (which consent will not be unreasonably withheld, conditioned or delayed); provided further that with respect to an adjournment or postponement pursuant to the foregoing clauses (ii) or (iii), Cantaloupe will not change the record date for the Special Meeting without 365’s prior written consent (which consent will not be unreasonably withheld, conditioned or delayed) (it being understood and agreed, that if required by applicable law, Cantaloupe will be entitled to change the record date for the Special Meeting if such requirement by applicable law is unrelated to any adjournment or postponement pursuant to the foregoing clauses (ii) or (iii)). Notwithstanding the foregoing, in the event that Cantaloupe postpones or adjourns the Special Meeting pursuant to the foregoing sentence, Cantaloupe will reconvene and hold the Special Meeting as promptly as reasonably practicable thereafter. Subject to Section 6.03 of the Merger Agreement, the Board will (i) recommend the approval and adoption of the Merger Agreement by Cantaloupe’s shareholders, (ii) use its reasonable best efforts to obtain the required Cantaloupe shareholder approval and (iii) otherwise comply with applicable law.

Cantaloupe and 365 have agreed (subject to the terms and conditions of the Merger Agreement) to cooperate with each other and use their reasonable best efforts to take, or cause to be taken, such actions and to do, or cause to be

done, such things as are necessary, proper or advisable under applicable law to consummate the Merger as promptly as practicable. These actions include, subject to the terms and conditions of the Merger Agreement, (i) preparing and filing with any governmental authority as promptly as practicable after the date of the Merger Agreement all documentation to effect all necessary filings, notices, petitions, statements, registrations, submissions of information, applications and other documents, (ii) obtaining and maintaining all permits, waivers and other confirmations required to be obtained from any governmental authority that are necessary to consummate the transactions contemplated by the Merger Agreement, in each case with respect to clauses (i) and (ii), subject to the parties’ obligations to cooperate pursuant to Section 8.01(b) of the Merger Agreement, (iii) defending or contesting any action, suit or proceeding challenging the Merger Agreement or the transactions contemplated by the Merger Agreement and (iv) executing and delivering any additional instruments necessary to consummate the transactions contemplated by the Merger Agreement.

In connection with the efforts referenced above, 365 will, and will cause its controlled affiliates, and their respective controlled representatives to, use their reasonable best efforts to take such steps as are necessary to avoid, eliminate or resolve each and every impediment and obtain all clearances, consents, approvals and waivers that may be necessary or required by any governmental authority, so as to enable the consummation of the Merger by the End Date, including:

provided that, notwithstanding anything to the contrary in the Merger Agreement, (i) no such Divestiture or Remedy will be required if such Divestiture or Remedy would result in a Substantial Detriment (as defined below), and (ii) neither party will be required to take any of the actions referred to above with respect to a Divestiture or Remedy unless the effectiveness thereof is conditioned on the occurrence of the effective time of the Merger. For purposes of the preceding sentence, a Remedy or Divestiture will be deemed to result in a “Substantial Detriment” if such actions, considered individually or collectively, (w) for avoidance of doubt, involve any Divestiture or Remedy with respect to any asset or business of 365, its affiliates, or any of their subsidiaries or affiliates, (x) involve any Divestiture or Remedy with respect to certain of Cantaloupe’s assets and businesses, (y) would be materially detrimental to the business, assets, or financial condition of Cantaloupe and its subsidiaries, taken as a whole, or (z) would reasonably be expected to result in a reduction of the annual consolidated revenues of Cantaloupe of more than 12.5% (using the fiscal year ended as of June 30, 2024 in determining (A) the expected reduction of the annual consolidated revenues of Cantaloupe and (B) whether the threshold set forth in this sentence is reasonably expected to be exceeded).

Under the HSR Act and related rules, the Merger may not be completed until HSR Act notification and report forms have been filed with the Antitrust Division of the United States Department of Justice and the Federal Trade Commission (which we refer to as the “FTC”) and the statutory waiting period applicable to the Merger has expired or been terminated.

At any time before the effective time of the Merger, notwithstanding the expiration or termination of the waiting period under the HSR Act, the FTC or the Antitrust Division of the Department of Justice, or any state could take such action under antitrust laws as it deems necessary or desirable in the public interest with respect to the Merger, including seeking to enjoin the completion of the Merger, to rescind the Merger or to conditionally approve the Merger upon the divestiture of assets, or to impose restrictions on the operations of Cantaloupe or 365 following the completion of the Merger. Private parties may also seek to take legal action under the antitrust laws under certain circumstances. There can be no assurance that the Merger will not be challenged on antitrust grounds or, if such a challenge is made, that the challenge will not be successful.

Outside of the United States, the Merger may be subject to the approval of certain other regulatory authorities. In each case, the Merger cannot be completed until the parties obtain clearance or approval to consummate the Merger or the applicable waiting periods have expired or been terminated.

The parties have agreed to use their reasonable best efforts to make the required filings as promptly as practicable, subject to cooperation between the parties pursuant to the Merger Agreement. The relevant regulatory authorities could take such actions under the applicable regulatory laws as they deem necessary or desirable, including enjoin the completion of the Merger, to rescind the Merger or to conditionally approve the Merger upon the divestiture of assets, or to impose restrictions on the operations of Cantaloupe or 365 following the completion of the Merger.

With respect to employees of Cantaloupe or its subsidiaries immediately before the effective time of the Merger (which we refer to as a “Cantaloupe Employee”), for a period of 12 months following the closing (or, if earlier, the termination of the applicable Cantaloupe Employee’s employment with 365, the surviving corporation and their affiliates), 365 will, or will cause the surviving corporation to, provide (a) a base salary or wage rate and target cash incentive compensation opportunities each of which is no less favorable than those provided to the Cantaloupe Employee immediately prior to the effective time of the Merger and (b) employee benefits (excluding equity or equity-based awards, retiree health and welfare benefits, transaction and retention benefits) that are substantially comparable in the aggregate to (i) those provided to the Cantaloupe Employee immediately prior to the effective time of the Merger and (ii) those provided by 365 and its affiliates to their similarly situated employees (either (i) or (ii), at 365’s election).

Without limiting the generality of the above, during the greater of (a) the protection period provided in any employment agreement, as applicable, and (b) the 12-month period following the effective time of the Merger, if the employment of any Cantaloupe Employee is terminated other than for “cause”, 365 will, or will cause the surviving corporation or any of its affiliates to, provide severance benefits to such terminated Cantaloupe Employee that are no less favorable than (i) at the election of 365, either (x) the severance benefits provided under any employee plan under which the Cantaloupe Employee was covered immediately prior to the effective time of the Merger or (y) the severance benefits to which similarly situated employees of 365 or its affiliates would be eligible to receive under 365’s or its affiliates’ severance policies, plans or arrangements, and (ii) for Cantaloupe Employees employed outside the U.S., the severance benefits required under applicable law.

With respect to any employee benefit plan, including any funded or unfunded and qualified or nonqualified employee benefit plan or program, maintained by 365, the surviving corporation or any of their affiliates (including, but not limited to, any vacation, paid time-off, car policy, and severance plans (including those where statutory benefits rely upon service time)), for all purposes, including determining eligibility to participate, level of benefits, vesting, benefit accruals and early retirement subsidies, each Cantaloupe Employee’s service with Cantaloupe or any of its subsidiaries prior to the effective time of the Merger (as well as service with any predecessor employer of Cantaloupe or any such subsidiary, to the extent service with the predecessor employer is recognized by Cantaloupe or such subsidiary under the comparable employee plans) will be treated as service with 365, the surviving corporation or their affiliates; provided, however, that such service need not be recognized to the extent that such recognition (i) would result in any duplication of benefits or apply to benefit accrual, (ii) is with respect to benefit accrual under any defined benefit pension plans or (iii) to the extent prior service is not credited to employees of 365 under such plans.

365 will use commercially reasonable efforts to waive, or will cause the surviving corporation or any of its affiliates to use commercially reasonable efforts to waive, any pre-existing condition limitations, exclusions, actively-at-work requirements and waiting periods under any welfare benefit plan maintained by 365, the surviving corporation or any of their affiliates in which any Cantaloupe Employee (or the dependents of any eligible Cantaloupe Employee) will be eligible to participate from and after the effective time of the Merger. 365 will use commercially reasonable efforts to recognize, or will cause the surviving corporation or any of its affiliates to use commercially reasonable efforts to recognize, the dollar amount of all co-payments, deductibles and similar expenses incurred by each Cantaloupe Employee (and his or her eligible dependents) under the applicable employee plan during the calendar year in which the effective time of the Merger occurs for purposes of satisfying such year’s deductible, co-payment and out-of-pocket limitations under the relevant welfare benefit plans in which such Cantaloupe Employee will be eligible to participate from and after the effective time of the Merger.

Prior to making any written or other material communications to the employees of Cantaloupe or its subsidiaries pertaining to compensation or benefit matters that are affected by the transactions contemplated by the Merger Agreement, Cantaloupe will provide 365 with a copy of the intended communication, 365 will have a reasonable period of time to review and comment on the communication, and Cantaloupe will consider any such comments in good faith.

365 has agreed to use its reasonable best efforts to take, or cause to be taken, all actions and to use its reasonable best efforts to do, or cause to be done, all things necessary, proper or advisable to obtain the proceeds of the Debt Financing on the terms and conditions described in the Debt Commitment Letter no later than the date upon which the Merger is required to be consummated pursuant to the terms hereof, including by (i) maintaining in full force and effect the Debt Commitment Letter and any definitive debt financing agreements (subject to replacement thereof in accordance with the Merger Agreement), (ii) negotiating and entering into definitive agreements with respect to the Debt Financing consistent with the terms and conditions contained in the Debt Commitment Letter (including, as necessary, the “flex” provisions contained therein or in any related fee letter) or on other terms acceptable to 365 that could not reasonably be expected to implicate certain prohibited modifications, (iii) satisfying on a timely basis all conditions to the funding of the Debt Financing set forth in the Debt Commitment Letter and the definitive financing agreements no later than at the closing of the Merger, (iv) consummating the Debt Financing at or prior to the closing of the Merger and (v) enforcing its rights under the Debt Commitment Letter in the event of a breach by the financing sources of their obligations under the Debt Commitment Letter.

365 has agreed that it will not, without the consent of Cantaloupe, (i) permit any amendment or modification to, or any waiver of any provision or remedy under, or replacement of, the Debt Commitment Letter or the definitive documentation relating to the financing if such amendment, modification, waiver or replacement (w) adds any new (or adversely modifies any existing) conditions to the funding of all or any portion of the Debt Financing in a manner that would reasonably be expected to prevent, impede or materially delay the closing of the Merger, (x) reduces the aggregate amount of the Debt Financing (unless the reduced amount is, together with certain other available sources, sufficient to fund the Transaction Amounts when due), (y) adversely affects the ability of 365 to enforce its rights under the Debt Commitment Letter or the definitive Debt Financing documents or (z) could otherwise reasonably be expected to prevent, impede or materially delay the consummation of the Merger or the transactions contemplated by the Merger Agreement or (ii) terminate the Debt Commitment Letter (other than upon the effectiveness of definitive Debt Financing documents or as permitted by the Merger Agreement). 365 is permitted to make customary modifications or amendments to the Debt Commitment Letter or the definitive documentation relating to the Debt Financing to (A) join additional lenders, arrangers, bookrunners or agents to the Debt Commitment Letter (as more specifically described in the Merger Agreement and the Debt Commitment Letter) or (B) implement the “flex” provisions of the fee letter entered into in connection with the Debt Commitment Letter.

In the event that any portion of the Debt Financing becomes unavailable, or the Debt Commitment Letter or any of the definitive debt financing agreements is withdrawn, repudiated, terminated or rescinded (other than as a result of a replacement permitted by the Merger Agreement), regardless of the reason therefor, then 365 will (i) use reasonable best efforts to arrange and obtain, as promptly as practicable, from the same or alternative financing sources, alternative financing in an amount sufficient, together with any equity commitment available to 365, Holdco, Holdco II and Merger Subsidiary, to fund the Transaction Amounts as and when due and (ii) promptly notify Cantaloupe of such unavailability and the reason therefor; provided that 365 is not required to obtain debt financing on terms and conditions that are, when taken as a whole, less favorable to 365 (and, after the consummation of the Merger, Cantaloupe) than the terms and conditions set forth in the Debt Commitment Letter as in effect on the date of the Merger Agreement (after giving effect to any “market flex” and/or similar provision).

365 has agreed to keep Cantaloupe informed in reasonable detail of the status of its efforts to arrange the Debt Financing and any other financing upon the written request of Cantaloupe and is required to give Cantaloupe prompt written notice of (i) any breach by any party to the Debt Commitment Letter or definitive debt financing agreements of any material provision which 365 has become aware, (ii) the expiration or termination in writing (or attempted or purported termination in writing, whether or not valid) of the Debt Commitment Letter, (iii) any written or electronic (including email) notice or communication by any Lender Party with respect to any actual or threatened breach, default (or allegation thereof), repudiation by any party to the Debt Commitment Letter or any definitive debt financing agreement or any refusal to provide, or stated intent that it will not provide, by any Lender Party, the full amount of the Debt Financing contemplated by the Debt Commitment Letter for any reason or (iv) 365’s good faith

belief, for any reason, that it may no longer be able to obtain all or any portion of the Debt Financing contemplated by the Debt Commitment Letter on the terms and conditions described therein.

The receipt or availability of any funds or financing (including, for the avoidance of doubt, the Debt Financing) by 365 or any of its respective affiliates or any other financing or other transactions is not a condition to any of 365’s obligations under the Merger Agreement.

Cantaloupe has agreed to, and to cause its subsidiaries to, provide all reasonable cooperation in connection with the arrangement of the Debt Financing of the type contemplated by the Debt Commitment Letter as in effect on the date of the Merger Agreement, including to:

Notwithstanding the foregoing, Cantaloupe and its subsidiaries are not required to:

Cantaloupe’s Board will not be required to adopt resolutions approving the agreements, documents or instruments pursuant to which the Debt Financing is obtained or pledge any collateral with respect to the Debt Financing prior to consummation of the Merger.

365 is required, promptly upon request by Cantaloupe, to reimburse Cantaloupe for all reasonable out-of-pocket costs and expenses incurred by Cantaloupe or its subsidiaries in connection with the cooperation contemplated by the Merger Agreement, except to the extent that the same results directly from (i) the gross negligence, bad faith, fraud or willful misconduct of Cantaloupe or any of their representatives, in each case, as determined by a final non-appealable judgment of a court of competent jurisdiction or (ii) any material inaccuracy of any historical financial information furnished in writing by or on behalf of Cantaloupe for use in connection with the Debt Financing. 365 is required to give Cantaloupe and its counsel a reasonable opportunity to review and comment on any materials that are to be presented during any road shows or bank presentations conducted in connection with the Debt Financing, and 365 is required to give due consideration to all reasonable additions, deletions or changes suggested thereto by Cantaloupe and its counsel. 365 is required to defend, indemnify and hold harmless Cantaloupe, its subsidiaries and their respective affiliates for and against any and all losses suffered or incurred by them in connection with the arrangement of the Debt Financing or any Alternative Financing (as defined in the Merger Agreement) and any information utilized in connection therewith (other than information provided by Cantaloupe expressly for use in connection therewith).

Cantaloupe is required to, and to cause its subsidiaries to, deliver all notices of prepayment with respect to the loans outstanding under the Credit Agreement (contingent upon the occurrence of the effective time of the Merger) and use reasonable best efforts to take all other actions required to facilitate at the effective time of the Merger the termination of all commitments outstanding under the Credit Agreement, the repayment in full of all obligations outstanding thereunder, the release of all liens securing such obligations and the release of all guarantees in connection therewith. Without limiting the generality of the foregoing, Cantaloupe and its subsidiaries are required to (a) use reasonable best efforts to deliver to 365 at least three business days prior to the consummation of the Merger a draft payoff letter and release documentation and (b) deliver to 365 at least one business day prior to the consummation of the Merger an executed payoff letter and related release documentation, in each case, with respect to the obligations under the Credit Agreement (which we refer to as the “Payoff Letter”), in form and substance reasonably satisfactory to 365, from the agent under the Credit Agreement, which Payoff Letter and executed related release documentation is required to, among other things, include the payoff amount and provide that liens (and guarantees), if any, granted in connection with the Credit Agreement relating to the assets, rights and properties of Cantaloupe and its subsidiaries securing such indebtedness will, upon the payment of the amount set forth in the Payoff Letter at the effective time of the Merger, be released and terminated. In no event will Cantaloupe or its subsidiaries be required to cause the termination of the Credit Agreement to be effective unless and until the effective time of the Merger has occurred and 365 has provided or caused to be provided to Cantaloupe or any of its subsidiaries funds (or 365 has directed Cantaloupe or any of its subsidiaries to use funds on their balance sheet) to pay in full the then-outstanding principal amount of and accrued and unpaid interest and fees under the Credit Agreement as set forth in the Payoff Letter.

365 has agreed to cause the surviving corporation, and the surviving corporation has agreed to, provide certain indemnification and insurance to the Indemnified Persons (as such term is defined below), including the following: