Welcome to our dedicated page for Pineapple Financial SEC filings (Ticker: PAPL), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
Pineapple Financial Inc. filings document a Canadian fintech and mortgage brokerage issuer with public-company reporting on operating results, capital structure, governance and risk. Current reports describe board-approved share repurchase authority, private placement and subscription receipt arrangements, executive and director agreements, and board or advisory-committee matters related to the company's digital asset treasury strategy.
Proxy and annual-meeting materials cover director elections, auditor ratification and audited consolidated financial statements. Other filings include Form 12b-25 reporting-status notices, registration statement materials, accounting timelines, capital-raising activity and the company's common-share securities.
Pineapple Financial Inc. reported that MNP LLP resigned as its independent registered public accounting firm on June 1, 2026, and the board and audit committee immediately appointed Davidson & Company LLP as the new auditor. MNP’s reports on the August 31, 2025 and 2024 financial statements contained an explanatory paragraph expressing substantial doubt about the company’s ability to continue as a going concern, but included no adverse opinions, disclaimers, or qualifications. The company states there were no disagreements or reportable events with MNP, and MNP has provided a confirming letter to the SEC.
The board and audit committee also approved a one-year Management Services and Advisory Agreement with Innovating Capital Management, LLC, which will manage asset, consulting and advisory services, including design and oversight of the company’s digital asset treasury strategy. The agreement renews automatically for additional one-year terms and can be terminated by either party with thirty days’ prior written notice. In parallel, the board adopted a Treasury Reserve Policy effective May 31, 2026, establishing governance, custody, reporting and risk-management frameworks for this digital asset treasury strategy.
Pineapple Financial Inc. expanded its share repurchase program, raising the total authorization from US$3,000,000 to up to US$15,000,000 of its outstanding common shares. The Board approved this increase and the company plans to begin repurchasing shares immediately under the initial US$3,000,000 authorization, subject to securities laws and having no material non-public information at the time of purchase.
The expanded authorization includes the original US$3,000,000 and an additional up to US$12,000,000, which may be used for future buybacks depending on further Board approval, solvency requirements, and the company’s financial condition and liquidity. Repurchases may occur from time to time in the open market under Rule 10b-18 and Rule 10b5-1, and the program can be modified, suspended, or terminated at the company’s discretion.
Pineapple Financial Inc. (PAPL) reports a sharply higher net loss driven by its new crypto strategy and financing costs. For the six months ended February 28, 2026, the company generated revenue of $1.4 million, slightly below the prior year, mainly from Canadian mortgage brokerage, subscriptions, insurance and related services.
Net loss widened to $25.9 million from $1.3 million, largely due to a $23.0 million non-cash fair value loss on digital assets and $3.3 million of financing-related costs, including warrant and equity line of credit expenses and higher interest on new borrowings. The company deployed $45.4 million into Injective (INJ) and other digital assets, which are now carried at $22.4 million after market-driven write-downs.
Cash increased to $17.7 million, supported by a January 2026 PIPE that raised $21.9 million in cash and $31.3 million in digital assets, and by a $19.0 million secured loan from FalconX at 10% interest. Despite $3.1 million of positive working capital, management discloses substantial doubt about the company’s ability to continue as a going concern, citing recurring losses and negative operating cash flows, even as it pursues cost reductions, staking income and liquidity initiatives.
Pineapple Financial Inc. director Anthony Georgiades filed an initial Form 3 reporting indirect holdings of common shares. The filing shows 1,315,789 common shares held by Innovating Capital GP, LLC, over which he has investment and dispositive power and may be deemed to beneficially own.
Georgiades disclaims beneficial ownership of these shares, except to the extent of any pecuniary interest. The filing records existing indirect ownership rather than a new purchase or sale.
Pineapple Financial Inc. held its 2026 Annual Meeting of Stockholders on March 13, 2026, where stockholders voted on the election of directors. Six nominees – Shubha Dasgupta, Kendall Marin, Drew Green, Paul Baron, Tasis Giannoukakis, and Anthony Georgiades – each received more votes for than against, with support levels ranging from 690,209.09 to 791,547.09 votes for and 77,636.00 to 179,984.00 votes against. Another matter received 2,709,116.09 votes for, 370,547.00 votes against, and 41,272.00 abstentions.
Pineapple Financial Inc. approved new employment agreements for its Chief Executive Officer, Shubha Dasgupta, and President and Chief Operating Officer, Kendall Marin. Each agreement runs for three years from February 5, 2026, with possible one-year extensions if agreed in writing at least 30 days before expiry.
Each executive will receive a base salary of $280,000 per year under the new contracts, which replace their prior employment agreements. The Board also approved a new agreement for Chairman Drew Green, who will receive a $20,000 monthly board fee, with his term dependent on ongoing nomination and re-election by shareholders or up to five years.
Pineapple Financial Inc. is asking stockholders to vote at its March 13, 2026 annual meeting on two key items: electing six directors and ratifying MNP LLP as independent auditor for the fiscal year ending August 31, 2026. The record date for voting is February 6, 2026. The proxy details board responsibilities, committee structures, governance practices, insider trading and clawback policies, and executive and director compensation.
New employment agreements raise base salaries for the CEO and President/COO to $280,000 each and increase the Chairman’s fee to $20,000 per month. The filing also outlines equity incentive plans, with 100,219 stock options outstanding under shareholder‑approved plans and 5,071,074 shares still available for future grants, as well as principal shareholdings, including three investors each holding over 5% of common shares.
Pineapple Financial Inc. reported a sharp deterioration in results for the three months ended November 30, 2025, and flagged substantial doubt about its ability to continue as a going concern. Revenue slipped to $721,727 from $766,074, while mortgage volume rose to $457.1M, showing higher activity but weaker net economics.
The company posted a net loss of $6,435,085 versus $656,894 a year earlier, mainly from a $6,140,379 non‑cash fair value loss on Injective crypto assets, whose value fell to $5,764,245 from an $11,896,002 cost base. Operating expenses excluding this loss declined as selling, marketing, and salary costs were cut.
As of November 30, 2025, Pineapple had negative shareholders’ equity of $(5,488,511), an accumulated deficit of $19,831,524, and a working capital deficit of $13,003,160. It also carried an $11,983,087 FalconX loan classified as current. Subsequent to quarter‑end, the company closed a $100M equity financing linked to the Injective initiative, received about $19.0M in cash, and repaid the FalconX loan.
Pineapple Financial Inc. filed a notification that it will be late in submitting its Quarterly Report on Form 10-Q for the quarter ended November 30, 2025. The company explains that it needs additional time to finalize its financial statements and for its independent public accounting firm to complete its audit. Pineapple Financial states it will use its best efforts to try to file the Form 10-Q within the five calendar-day extension period permitted under Rule 12b-25(b) of the Securities Exchange Act.
Injective Foundation and Glenn Kennedy filed a Schedule 13D reporting beneficial ownership of 9,615,385 Pineapple Financial Inc. common shares, representing 36.99% of the class. These shares arise from subscription receipts purchased by the Foundation, each exchangeable into one common share after escrow conditions were satisfied.
The Foundation acquired 9,615,385 subscription receipts at a purchase price of $4.16 per receipt, for an aggregate consideration of 2,877,697 INJ tokens, as part of Pineapple’s INJ digital asset treasury strategy. The filing notes that the Foundation holds the shares directly, while Kennedy may be deemed to share voting and dispositive power but disclaims beneficial ownership.
The Foundation and Kennedy may discuss Pineapple’s business, strategy and board composition with management and other shareholders. Under the purchase agreement, Pineapple added Anthony Georgiades to its board after consultation with the Foundation. A lock-up agreement restricts the Foundation from disposing of its securities for 12 months after the effective date, with staged 25% releases if the share price reaches $7.588, $11.382, $15.176 or $18.970.