Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 12

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 12
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 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 (which we refer to as the “preferred stock redemption payment”). Upon the Redemption, all rights of the holders thereof will terminate, except for the right to receive the preferred stock redemption payment. For more information, see the section of this proxy statement titled “ The Merger Agreement—Redemption of Preferred Stock”. The Special Meeting (Page 23) Date, Time and Place of the Special Meeting The Special Meeting will be held on September 4, 2025, at 8:00 a.m., Eastern time, virtually at www.virtualshareholdermeeting.com/CTLP2025SM. Purpose of the Special Meeting At the Special Meeting, you will be asked to consider and vote upon:

| 1. | The Merger Proposal: To approve and adopt the Merger Agreement (which we refer to as the “Merger Proposal”); |

| 2. | Advisory Compensation Proposal: To approve, by a non-binding, advisory vote, the compensation arrangements that will or may become payable to our named executive officers in connection with the Merger (which we refer to as the “Advisory Compensation Proposal”); and |

| 3. | Adjournment Proposal: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 we refer to as the “Adjournment Proposal”). |

In this proxy statement, references to the “proposals” refer, collectively, to proposals 1, 2 and 3 listed above.

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#### TABLE OF CONTENTS
Record Date and Voting Information

The holders of record of Cantaloupe stock as of the close of business on July 21, 2025 (which we refer to as the “record date”) will be entitled to receive notice of and to vote at the Special Meeting. As of the record date, there were 73,289,054 shares of our common stock outstanding and 385,782 shares of our preferred stock outstanding.

Each share of common stock outstanding as of the record date will be