Pineapple Financial Inc.

Evaluation of Disclosure Controls and Procedures

Management, with the participation of the Company’s Chief Executive Officer and Chief Financial Officer, evaluated the effectiveness of the Company’s disclosure controls and procedures, as defined in Rules 13a-15(e) and 15d-15(e) under the Securities Exchange Act of 1934, as amended, as of May 31, 2026.

Disclosure controls and procedures are designed to provide reasonable assurance that information required to be disclosed by the Company in reports filed or submitted under the Exchange Act is recorded, processed, summarized and reported within the time periods specified in the SEC’s rules and forms, and that such information is accumulated and communicated to management, including the Chief Executive Officer and Chief Financial Officer, as appropriate, to allow timely decisions regarding required disclosure.

Based on this evaluation, the Chief Executive Officer and Chief Financial Officer concluded that the Company’s disclosure controls and procedures were not effective as of May 31, 2026 due to the material weakness in internal control over financial reporting described below.

Management has identified a material weakness in the Company’s internal control over financial reporting related to insufficient segregation of duties within the finance function, primarily due to a limited number of personnel responsible for financial reporting, accounting, review and disclosure functions. This limitation affects the Company’s ability to consistently maintain an appropriate level of independent review over complex accounting areas, including, among others, share-based compensation, warrant liability valuation, derivative instruments, digital asset transactions, staking income, crypto asset custody reconciliations, restricted cash and financing arrangements, and related financial statement disclosures.

During the nine months ended May 31, 2026, the Company expanded its activities to include a Digital Asset Treasury strategy involving digital assets. As part of management’s evaluation of disclosure controls and procedures, management considered controls over the existence, custody and valuation of digital assets, wallet and custodian reconciliations, authorization of digital asset transactions, recognition of staking income, assessment of the principal market and fair value pricing inputs, restricted cash and collateral arrangements, and completeness and accuracy of related disclosures. Management continues to enhance its control environment in these areas; however, due to the limited number of finance personnel and the resulting segregation of duties limitation described above, the material weakness remained unremediated as of May 31, 2026.

A material weakness is a deficiency, or a combination of deficiencies, in internal control over financial reporting such that there is a reasonable possibility that a material misstatement of the Company’s financial statements will not be prevented or detected on a timely basis.

Notwithstanding the material weakness described above, management believes that the condensed interim consolidated financial statements included in this Quarterly Report fairly present, in all material respects, the Company’s financial position, results of operations and cash flows in accordance with U.S. GAAP.

Remediation Plan

Management is committed to improving the Company’s internal control over financial reporting. Subject to available resources, management intends to continue enhancing the Company’s control environment by implementing additional review procedures, improving documentation of complex accounting estimates and judgments, enhancing reconciliations and review controls over digital asset activities, and evaluating the need for additional finance, accounting, valuation or compliance resources. The material weakness will not be considered remediated until the applicable controls have been designed, implemented and operated effectively for a sufficient period of time.

Changes in Internal Control over Financial Reporting

Other than the ongoing enhancements described above, there were no changes in the Company’s internal control over financial reporting during the quarter ended May 31, 2026 that materially affected, or are reasonably likely to materially affect, the Company’s internal control over financial reporting.