Company: CTLPP
Filing Date: 2025-07-11
Form Type: PREM14A
Source: 0001140361-25-025663
Chunk: 54

Company: CANTALOUPE, INC.
Filing Date: 2025-07-11
Form: PREM14A
Chunk 54
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 & Co.

430 Park Avenue, 14th Floor

New York, NY 10022

Shareholders may call toll-free: (800) 662-5200

Brokers, Banks, and Other Nominees may call collect: (203) 658-9400

Email: ctlp@info.sodali.com

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#### TABLE OF CONTENTS
<div align='center'>**PROPOSAL 1: APPROVAL AND ADOPTION OF THE MERGER AGREEMENT**</div>

#### Merger Proposal
We are asking you to approve and adopt the Merger Agreement. If the Merger Agreement is approved and adopted by our shareholders and all other conditions to the closing of the Merger are either satisfied or validly waived, Merger Subsidiary will merge with and into Cantaloupe with Cantaloupe surviving the Merger as wholly owned subsidiary of Holdco II. Our common stock is currently traded on the Nasdaq under the symbol “CTLP”. If the Merger is completed, we will cease to be an independent public company and will become an indirect wholly owned subsidiary of 365. Following the completion of the Merger, the registration of our common stock and our reporting obligations under the Exchange Act will be terminated. In addition, upon the completion of the Merger, our common stock will no longer be listed on any stock exchange or quotation system, including the Nasdaq. Additionally, pursuant to the Merger Agreement, upon the terms and subject to the conditions set forth therein, Cantaloupe is required to redeem all of the outstanding shares of preferred stock immediately prior to the consummation of the Merger in accordance with the applicable redemption provisions contained in the Cantaloupe Articles, at a redemption price payable in cash, by or on behalf of Cantaloupe, in an 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.

For a summary of and detailed information regarding this proposal, see the information about the Merger Agreement and the Merger throughout this proxy statement, including the information set forth in the sections of this proxy statement titled “ The Merger ” and “ The Merger Agreement ”. A copy of the Merger Agreement is attached to this proxy statement as Annex A. You are urged to read the Merger Agreement carefully in its entirety.

We cannot complete the Merger without, assuming a quorum is present at the Special Meeting