Company: CTLPP
Filing Date: 2025-07-11
Form Type: PREM14A
Source: 0001140361-25-025663
Chunk: 27

Company: CANTALOUPE, INC.
Filing Date: 2025-07-11
Form: PREM14A
Chunk 27
---
 its subsidiaries’ cooperation in connection with 365’s arrangement of the Debt Financing.

For more information on fees and expenses incurred in connection with the Merger Agreement and the Merger, see the section of this proxy statement titled “ The Merger Agreement—Fees and Expenses ”.

#### Help in Answering Questions
We greatly appreciate your cooperation in voting your shares. If you have any questions about the Special Meeting or the Merger after reading this proxy statement, our shareholders may contact Sodali & Co. (which we refer to as “Sodali”), our proxy solicitor, by telephone at (800) 662-5200 and brokers, banks and other nominees may contact Sodali at (203) 658-9400.

<div align='center'>11</div>

TABLE OF CONTENTS

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER 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.

| Q: | Why am I receiving these materials? |

| A: | You are receiving this proxy statement and the accompanying proxy card because you owned shares of common stock or shares of preferred stock at the close of business on [  ], 2025, the record date for the Special Meeting. Our Board is soliciting proxies for use at the Special Meeting to consider and vote upon the proposal to approve and adopt the Merger Agreement and the other proposals to be voted upon at the Special Meeting. These proxy materials provide you information for use in determining how to vote in connection with the matters to be considered at the Special Meeting. |

| Q: | When and where is the Special Meeting? |

| A: | The Special Meeting is scheduled to be held virtually via live webcast on [  ], 2025, at [  ], Eastern time (unless the Special Meeting is adjourned or postponed). 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. |

| Q: | What matters will be