ANNUAL REPORT PURSUANT TO SECTION13 OR 15(d)OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscalyear endedJune30, 2025OR ☐TRANSITION REPORT PURSUANT TO SECTION13 OR 15 (d)OF THE EXCHANGE ACT OF 1934 For the transition period from ____________________ to _____________________Commission file number001-33365 Cantaloupe,Inc.____________________________________________________________________________________________ (Exact name of registrant as specified in its charter) Pennsylvania (State or other jurisdiction of incorporation or organization)(I.R.S. Employer Identification No.) 101 Lindenwood DriveMalvern,Pennsylvania(Address of principal executive offices) (Registrant’s telephone number, including area code) (610)989‑0340 Securities registered pursuant to Section12(b)of the Act: Securities registered pursuant to Section12(g)of the Act: None Indicate by check mark if the registrant is a well-known seasoned issuer, as defined in Rule405 of the Securities Act. Yes☐No☒ Indicate by check mark if the registrant is not required to file reports pursuant to Section13 or Section15(d)of the Act.Yes☐No☒ Indicate by check mark whether the registrant (1)has filed all reports required to be filed by Section13 or 15(d)of the Securities Exchange Act of 1934 during thepreceding 12months (or for such shorter period that the registrant was required to file such reports), and (2)has been subject to such filing requirements for the past90days.Yes☒No☐ Indicate by check mark whether the registrant has submitted electronically and posted on its corporate Web site, if any, every Interactive Data File required to besubmitted and posted pursuant to Rule405 of Regulation S-T (§232.405 of this chapter) during the preceding 12months (or for such shorter period that the registrantwas required to submit and post such files)Yes☒No☐ Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerginggrowth company. See the definitions of “large accelerated filer”, “accelerated filer”, “smaller reporting company,” and “emerging growth company” in Rule12b‑2 of theExchange Act. Large accelerated filer Non-accelerated filer (Do not check if a smaller reporting company)Emerging growth company If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revisedfinancial accounting standards provided pursuant to Section 13(a) of the Exchange Act.☐ Indicate by check mark whether the registrant has filed a report on and attestation to its management’s assessment of the effectiveness of its internal control overfinancial reporting under Section 404(b) of the Sarbanes-Oxley Act (15 U.S.C. 7262(b)) by the registered public accounting firm that prepared or issued its audit report.☑ If securities are registered pursuant to Section 12(b) of the Act, indicate by check mark whether the financial statements of the registrant included in the filing reflect thecorrection of an error to previously issued financial statements.☐ Indicate by check mark whether any of those error corrections are restatements that required a recovery analysis of incentive-based compensation received by any of theregistrant's executive officers during the relevant recovery period pursuant to §240.10D-1(b).☐ The aggregate market value of the voting and non-voting common equity held by non-affiliates of the registrant computed by reference to the price at which thecommon equity was last sold as of the last business day of the registrant’s most recently completed second fiscal quarter, which ended December 31, 2024, was $562.9million. As of September2, 2025, there were73,368,777outstanding shares of common stock, no par value. CANTALOUPE,INC. TABLE OF CONTENTS PARTIItem1.Business.51A.Risk Factors.151B.Unresolved Staff Comments.261C.Cybersecurity.262.Properties.273.Legal Proceedings.274.Mine Safety Disclosures.27PARTIIItem5.Market for Registrant’s Common Equity, Related Stockholder Matters and Issuer Purchases of EquitySecurities.286.[Reserved].297.Management’s Discussion and Analysis of Financial Condition and Results of Operations.307A.Quantitative and Qualitative Disclosures About Market Risk.418.Financial Statements and Supplementary Data.429.Changes in and Disagreements With Accountants on Accounting and Financial Disclosure.879A.Controls and Procedures.879B.Other Information.889C.Disclosure Regarding Foreign Jurisdictions that Prevent Inspections.88PARTIIIItem10.Directors, Executive Officers and Corporate Governance.8911.Executive Compensation.9512.Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters.11113.Certain Relationships and Related Transactions, and Director Independence.11214.Principal Accounting Fees and Services.113PARTIVItem15.Exhibits, Financial Statement Schedules.11516.Form 10-K Summary.117 PART I In this Annu