Company: CTLPP
Filing Date: 2025-06-16
Form Type: DEFA14A
Source: 0001104659-25-059925
Chunk: 0

Company: CANTALOUPE, INC.
Filing Date: 2025-06-16
Form: DEFA14A
Chunk 0
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<div align='center'>UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934</div>

Filed by the Registrant x

Filed by a Party other than the Registrant ¨

Check the appropriate box:

| ¨ | Preliminary Proxy Statement |

| ¨ | Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) |

| ¨ | Definitive Proxy Statement |

| ¨ | Definitive Additional Materials |

| x | Soliciting Material under Rule 14a-12 |

<div align='center'>Cantaloupe, Inc.

(Name of registrant as specified in its charter)

(Name of person(s) filing proxy statement, if other than the registrant)</div>

Payment of Filing Fee (Check all boxes that apply):

| x | No fee required. |

| ¨ | Fee paid previously with preliminary materials |

| ¨ | Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11 |

On June 16, 2025, Ravi Venkatesan, the CEO of Cantaloupe, Inc. (“Cantaloupe”),
emailed the below communications related to the proposed acquisition of the Company by 365 Retail Markets, LLC, a Delaware limited liability
company (“365”), pursuant to the Agreement and Plan of Merger, dated as of June 15, 2025, by and among, inter alia,
Cantaloupe and 365:

Subject:
We’re Joining with 365 Retail Markets – Here’s What It Means for You

Dear [Customer Name],

As a valued customer to Cantaloupe, I’m pleased to share that
today our organization entered into an agreement to be acquired by 365 Retail Markets, LLC (“365”). This is an exciting milestone
and a bold step forward designed to enhance what we deliver to you every day.

You have come to rely on Cantaloupe for our reliability, innovation,
and dedication to excellent service. Let me reassure you: that commitment remains unchanged.

In fact, it’s about to get better.

The transaction is expected to close in the second half of 2025, pending
all necessary approvals. In the meantime, it's business