Company: CTLPP
Filing Date: 2025-06-16
Form Type: DEFA14A
Source: 0001104659-25-059932
Chunk: 1

Company: CANTALOUPE, INC.
Filing Date: 2025-06-16
Form: DEFA14A
Chunk 1
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 bold step by combining with a company that not only shares
our vision but also brings complementary strengths that will accelerate our impact.

Together, we are poised to create an end-to-end solution for operators
across industries, enabling smarter, more connected, and more consumer-centric retail experiences. The strategic fit is strong –
by joining together, we’re creating better value for our customers, accelerating innovation, and expanding our reach to serve more
than 1.3 million operator locations across over 30 countries.

The transaction is expected to close in the second half of 2025, pending
regulatory and shareholder approvals. In the meantime, it’s business as usual, and we’ll be keeping our teams informed as
appropriate.

As we communicate this news to our teams, I want to ensure that we’re
aligned on our messaging and approach, thus attached you will find helpful employee FAQ’s. Our people are the foundation of everything
we’ve built, and their talent, culture, and commitment to innovation are precisely what made this partnership so compelling to 365.
We need to be clear that this acquisition represents growth and opportunity, not uncertainty or change for the sake of change.

During our all-hands meeting, we will further discuss the transaction,
address employee questions, and share more details on the remarkable opportunity this is for our business, people and customers.

This is a defining moment for Cantaloupe, and I’m confident that with your leadership and our team’s dedication, we’ll navigate this transition successfully while maintaining the momentum that got us here.Thank you for your continued leadership and partnership
as we embark on this exciting new chapter.

With appreciation,

Ravi Venkatesan

CEO, Cantaloupe, Inc.

Cautionary Statement Regarding Forward-Looking Statements

This communication contains “forward-looking statements”,
as that term is defined under the Private Securities Litigation Reform Act of 1995 and other securities laws, regarding Cantaloupe, Inc.
(“Cantaloupe”) and 365 Retail Markets, LLC (“365”) and the potential transaction between Cantaloupe and 365, including,
but not limited to, statements about the strategic rationale and benefits of the proposed transaction between Cantaloupe and 365, including
future financial and operating results, Cantaloupe’s or 365’s plans, objectives, expectations and intentions and the expected
timing of completion of the proposed transaction. You can generally identify forward-looking statements by the use of forward-looking
terminology such as