Company: CTLPP
Filing Date: 2025-07-11
Form Type: PREM14A
Source: 0001140361-25-025663
Chunk: 41

Company: CANTALOUPE, INC.
Filing Date: 2025-07-11
Form: PREM14A
Chunk 41
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. 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 loss for U.S. federal income tax purposes in an amount equal to the difference, if any, between the amount of cash received with respect to such shares of common stock or preferred stock, as applicable, and your adjusted tax basis in such shares. If you are a Non-U.S. Holder, you generally will not be subject to U.S. federal income tax with respect to the receipt of cash in exchange for our common stock pursuant to the Merger, or the receipt of the preferred stock redemption payment in connection with the Redemption, unless you have certain connections to the United States or we are or have been a United States real property holding corporation and certain other circumstances apply. |

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.

| Q: | What happens if the Merger is not completed? |

| A: | 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 |

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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