Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 2

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 2
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pe refers to as the “Adjournment Proposal”.

The Board unanimously recommends that you vote “FOR” the Advisory Compensation Proposal and that you vote “FOR” the Adjournment Proposal.

As of the close of business on July 21, 2025 (which we refer to as the “record date”), we had outstanding 73,289,054 shares of common stock and 385,782 shares of Series A Convertible Preferred Stock (which we refer to as “preferred stock” and, together with common stock, “Cantaloupe stock”).

Each member of the Board and Hudson Executive Capital LP, collectively representing approximately 17.9% of the voting power of the shares of Cantaloupe stock outstanding as of the record date and entitled to vote at the Special Meeting, have entered into Voting Agreements with 365 to, among other things, vote in favor of the proposals set forth in this proxy statement. For more information, see the section of this proxy statement titled “ The Merger—Voting Agreements ”.**

TABLE OF CONTENTS

Your vote is very important, regardless of the number of shares you own. Cantaloupe cannot complete the Merger without the affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of common stock and preferred stock (voting on an as-converted basis) entitled to vote thereon, voting together as a single class. Each share of common stock outstanding as of the record date will be entitled to one vote on each matter submitted to our shareholders for approval at the Special Meeting. Each share of preferred stock outstanding as of the record date will be entitled to vote on an as-converted basis, with each share of preferred stock outstanding as of the record date entitling the holder thereof to 0.1988 of a vote on each matter submitted to our shareholders for approval at the Special Meeting (with any fractional vote determined on an aggregate conversion basis being rounded to the nearest whole number). In the materials accompanying this letter, you will find a Notice of Special Meeting of shareholders, a proxy statement relating to the actions to be taken by Cantaloupe’s shareholders at the Special Meeting or any adjournment or postponement thereof and a proxy card. The proxy statement includes other important information about the Merger Agreement and the Merger. Cantaloupe encourages you to read the entire proxy statement and its annexes carefully. A copy of the Merger Agreement is attached as Annex A to the accompanying proxy statement. You may