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

Company: CANTALOUPE, INC.
Filing Date: 2025-07-11
Form: PREM14A
Chunk 11
---
, virtually at www.virtualshareholdermeeting.com/CTLP2025SM. Purpose of the Special Meeting At the Special Meeting, you will be asked to consider and vote upon:

| 1. | The Merger Proposal: To approve and adopt the Merger Agreement (which we refer to as the “Merger Proposal”); |

| 2. | Advisory Compensation Proposal: To approve, by a non-binding, advisory vote, the compensation arrangements that will or may become payable to our named executive officers in connection with the Merger (which we refer to as the “Advisory Compensation Proposal”); and |

| 3. | Adjournment Proposal:To approve the adjournment of the Special Meeting from time to time, if necessary or appropriate (as determined by the Board or the chairperson of the meeting) to solicit additional proxies to vote in favor of the proposal to approve and adopt the Merger Agreement, in the event that there are insufficient votes at the time of the Special Meeting to establish a quorum or approve and adopt the Merger Agreement or with 365’s prior written consent (which we refer to as the “Adjournment Proposal”). |

In this proxy statement, references to the “proposals” refer, collectively, to proposals 1, 2 and 3 listed above.

3

#### TABLE OF CONTENTS
Record Date and Voting Information

The holders of record of Cantaloupe stock as of the close of business on [  ], 2025 (which we refer to as the “record date”) will be entitled to receive notice of and to vote at the Special Meeting. As of the record date, there were [  ] shares of our common stock outstanding and [  ] shares of our preferred stock outstanding.

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 accordance with the Nasdaq rules, banks, brokers and other nominees who hold shares of common stock in “street name” for their customers do not have