Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 41

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 41
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 outside the control of Cantaloupe or 365 could result in the Merger being completed at a later time or not being completed at all. |

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TABLE OF CONTENTS

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. If you are a shareholder of record with your shares held in certificated form, you will receive a letter of transmittal with instructions for returning such letter of transmittal and how to send your share certificates to the Paying Agent in connection with the Merger. Please do not send in your stock certificates with your proxy card. |

| Q: | What are the material U.S. federal income tax consequences of the Merger and the Redemption? |

| A: | The exchange of shares of our common stock for cash pursuant to the Merger, and the receipt of the preferred stock redemption payment in connection with the Redemption, in each case, will generally be a taxable transaction for U.S. federal income tax purposes to U.S. Holders. If you are a U.S. Holder and your shares of our common stock are converted into the right to receive cash in the Merger, or your shares of our preferred stock are redeemed for the preferred stock redemption payment, you will generally recognize gain or