Company: CTLPP
Filing Date: 2025-07-11
Form Type: PREM14A
Source: 0001140361-25-025663
Chunk: 40

Company: CANTALOUPE, INC.
Filing Date: 2025-07-11
Form: PREM14A
Chunk 40
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 and other shares |

18

TABLE OF CONTENTS

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.

| Q: | When do you expect the Merger to be completed? |

| A: | 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. However, the Merger is subject to various regulatory approvals and other conditions, which are described in more detail in this proxy statement, and it is possible that factors outside the control of Cantaloupe or 365 could result in the Merger being completed at a later time or not being completed at all. |

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.

| Q: | If the Merger is completed, how will I receive the cash for my shares of common stock? |

| A: | If the Merger is completed and your shares of common stock are held in book-entry through the Depositary Trust Company (which we refer to as “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 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. |

| Q: | Should I send in my stock certificates now? |

| A: | No. Please do not send your stock certificates now