Cantaloupe, Inc. Announces Redemption of Series A Convertible Preferred Stock Ahead of Merger

Key Points for Investors

• Redemption of Series A Convertible Preferred Stock: Cantaloupe, Inc. (“the Company”) has announced its intention to redeem all outstanding Series A Convertible Preferred Stock (CUSIP NO. 138103205) immediately prior to the closing of its merger with 365 Retail Markets, LLC.
• Planned Merger: The redemption is contingent upon the closing of the merger, scheduled for May 8, 2026. If the merger does not occur, the redemption will not take place.
• Redemption Price: Each share of Preferred Stock will be redeemed for \$62.90 in cash, consisting of the \$11.00 original price plus \$51.90 in accrued and unpaid cumulative dividends as of the Redemption Date.
• Conversion Option: Holders of Preferred Stock have the right to convert their shares (including accrued dividends) into common stock at any time before the Redemption Date. If conversion is elected, holders receive the Merger Consideration for each share of common stock instead of the Redemption Price.
• Redemption Notice is Revocable: The Company explicitly states that this notice of redemption can be revoked at its sole discretion for any reason. If revoked, no shares will be redeemed on the Redemption Date, but the Company reserves the right to reissue a new notice in the future.

Details of the Merger and Redemption

Cantaloupe, Inc. will merge with a subsidiary of 365 Retail Markets, LLC, with Cantaloupe surviving as a wholly-owned, indirect subsidiary. This transaction is governed by the Merger Agreement dated June 15, 2025. The Company has filed copies of both its Articles of Incorporation and the Merger Agreement with the SEC, making these documents publicly accessible.

As part of the merger process, all outstanding Series A Convertible Preferred Stock will be redeemed for cash immediately prior to the merger closing. The total redemption price per share will be \$62.90, based on the anticipated cumulative dividends as of the Redemption Date. Dividends will continue to accrue up to the Redemption Date, and will cease thereafter.

Important Notes for Shareholders

• Action Required for Physical Shareholders: Holders of physical certificates must return their certificates and execute a Letter of Transmittal to receive the Redemption Price. Payment will be processed by Equiniti Trust Company, LLC, the appointed Redemption Agent.
• Risk of Delivery: The method and risk of shipment of certificates to the Redemption Agent lies with the shareholder. Registered mail with return receipt is recommended.
• Holders of Shares in “Street Name”: Beneficial owners whose shares are held by brokers or other nominees must instruct their registered holders to act on their behalf.
• Right to Convert: Shareholders may convert their Preferred Stock into common stock at any time before the Redemption Date. If they do, they will receive the Merger Consideration (as defined in the Merger Agreement) for each share of common stock, less any applicable withholding taxes, instead of the Redemption Price.
• Deadline for Action: The key date for both redemption and potential conversion is May 8, 2026.
• Loss of Rights After Redemption: On and after the Redemption Date, Preferred Stock will no longer be outstanding, dividends will cease to accrue, and all rights (except for receiving the Redemption Price) will terminate.
• Contact Information: Shareholders with questions should contact the Redemption Agent at (800) 937-5449.

Potential Price-Sensitive Implications

• Signaling a Major Corporate Event: The planned redemption and merger represent a significant corporate transaction that could result in material changes to the Company’s structure and value.
• Impact on Preferred and Common Stockholders: Preferred shareholders face a choice between a fixed cash payout or conversion into common stock to participate in the merger consideration. This could influence the trading dynamics of both preferred and common shares leading up to the Redemption Date.
• Uncertainty Due to Revocability: The Company’s right to revoke the redemption notice introduces uncertainty, which may affect share prices as investors assess the probability of the merger closing as scheduled.

Summary Table

Conclusion

This redemption and the associated merger are highly significant events for Cantaloupe, Inc. investors. Shareholders must make timely decisions regarding their Preferred Stock, and the outcome of the merger could materially affect the value of both preferred and common shares. The ability of the Company to revoke the notice adds a layer of uncertainty that investors should monitor closely.

Disclaimer: This article is for informational purposes only and does not constitute investment advice. Investors are encouraged to read the full documents filed with the SEC and consult with their financial advisors regarding the implications of the merger and redemption. The situation remains subject to change, including the potential revocation of the redemption notice by the Company.

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