Company: CTLPP
Filing Date: 2025-06-16
Form Type: DEFA14A
Source: 0001104659-25-059932
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:

CTLP CEO Letter to SLT

Subject:
Strategic Transaction Update: Cantaloupe and 365 Retail Markets

Dear Senior Leadership Team,

Today, we announced thatCantaloupe, Inc. (“Cantaloupe”) has entered into a definitive agreement to be acquired by 365 Retail
Markets, LLC (“365”).

As you all can imagine, this transaction represents a transformative
moment for our company and marks the next chapter in our growth story. Over the years, we’ve built something truly special at Cantaloupe
– our offerings in payments, telemetry, kiosk-based marketplaces, vending management software, and smart store innovation have positioned
us as a driving force in self-service commerce. Now, we’re taking the next