Pineapple Financial Inc.

(Former name or former address, if changed since last report)

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Emerging growth☒

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Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers.

Chief Financial Officer Transition

On October 9, 2026, the Board of Directors (the “Board”) of Pineapple Financial Inc. (the “Company”) approved a transition of the Company’s finance leadership. Effective October 15, 2026, Usman Maher was appointed Chief Financial Officer and Chief Strategy Officer of the Company.

Syed Sarfraz Habib, who has served as the Company’s Chief Financial Officer, was appointed Chief Accounting Officer and Controller of the Company. Mr. Habib’s transition is not the result of any disagreement with the Company on any matter relating to the Company’s operations, policies or practices.

The appointment reflects the Company’s focus on strengthening its finance and strategy functions as it scales the Pentiv platform, including institutional-grade financial planning and analysis, capital-markets execution, and the reporting infrastructure to support the Company’s commercial milestones.

Mr. Maher, age 40, brings nearly two decades of experience across hedge fund investing, private equity, special situations credit, and high-growth financial technology. From 2022 to 2026, he served as Senior Director, Strategic Finance at SoFi Technologies, Inc., where he built the finance function for SoFi’s member platform. From 2020 to 2021, he served as a consultant on transactions and diligence matters for investment management firms. From 2016 to 2020, he served in roles of increasing seniority, most recently Vice President, at Lone Star Funds, focused on private equity and special situations investments. Mr. Maher has been a CFA charterholder since 2011 and holds an M.B.A. from the University of Chicago Booth School of Business.

Employment Agreement

In connection with Mr. Maher’s appointment, the Company and Mr. Maher entered into an Executive Employment Agreement, dated as of October 9, 2026 (the “Employment Agreement”), under which Mr. Maher will receive an annual base salary of $250,000, accruing from October 1, 2026. Mr. Maher will participate in the Company’s Management Incentive Plan, with a target annual bonus of 100% of base salary and a payout range of 50% of base salary at threshold to 150% at maximum. Mr. Maher will also be granted equity awards subject to Board and Compensation Committee approval and to the terms of the Company’s 2022 Omnibus Equity Incentive Plan and 2021 Stock Option Plan. The foregoing description of the Employment Agreement does not purport to be complete and is qualified in its entirety by reference to the full text of the Employment Agreement, which is filed as Exhibit 10.1 to this Current Report and incorporated herein by reference.

Principal Financial Officer and Principal Accounting Officer Designations

Mr. Habib shall continue to serve as the Company’s “principal financial officer” and “principal accounting officer” for all purposes of the U.S. Securities Exchange Act of 1934 and the rules thereunder through the filing of the Company’s Annual Report on Form 10-K for the fiscal year ended August 31, 2026 (the “Form 10-K”) and the certifications and other filings related thereto. Upon the filing of the Form 10-K, Mr. Maher shall, without further action of the Board, assume the designation of “Principal Financial Officer”, and Mr. Habib shall continue as “Principal Accounting Officer” of the Company.

Item 7.01 Regulation FD Disclosure.

On October 15, 2026, the Company issued a press release announcing the matters described in this Current Report and made available an investor presentation. Copies of the press release and the investor presentation are furnished as Exhibit 99.1 and Exhibit 99.2, respectively, to this Current Report. The information in this Item 7.01, including Exhibits 99.1 and 99.2, is being furnished and shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section, and shall not be deemed incorporated by reference into any filing under the Securities Act of 1933, as amended, except as expressly set forth by specific reference in such filing.