Pineapple Financial Inc. SEC Filings

Pineapple Financial Inc. reported that its board has appointed Anthony Georgiades, nominated by the Injective Foundation, as a new director effective December 18, 2025. His appointment fulfills a commitment under a previously disclosed securities purchase agreement related to a private placement of subscription receipts priced at $3.80 or $4.16 per subscription receipt for different purchasers.

The board also created a Special Advisory Committee to oversee the company’s digital asset treasury strategy and treasury reserve policy. Georgiades will chair this committee, which initially includes directors Drew Green and Paul Baron. The committee may hire independent legal, financial, and compliance advisors, including three strategic advisors identified by the Injective Foundation, each receiving annual cash compensation of $5,000.

Pineapple Financial Inc. is registering 25,682,046 common shares for resale by existing investors, largely tied to a recent private placement that raised approximately $100 million to fund an INJ-focused digital asset treasury strategy. The resale includes shares issuable from subscription receipts and 1,039,346 warrant shares for a consultant, and the company will not receive any proceeds from investors’ sales. As of December 12, 2025, 1,345,941 common shares were outstanding, so the registered amount is large relative to the current equity base. The company plans to concentrate its treasury in INJ tokens, use staking and derivatives, employ external asset managers, and has drawn on a $15 million credit facility to buy additional INJ, while highlighting extensive risks around digital-asset volatility, regulation, custody, illiquidity and potential discounts of its share price to net asset value, alongside its existing Canadian mortgage technology and brokerage business.

Pineapple Financial Inc. (PAPL) filed an amended annual report to revise its assessment of controls and procedures for the year ended August 31, 2025. The company now concludes that its disclosure controls and procedures were not effective as of that date, citing the late filing of its annual report and a material weakness in internal control over financial reporting related to segregation of duties in the finance function.

As of August 31, 2025, the aggregate market value of common shares held by non-affiliates was about $5.391 million, and 1,345,941 common shares were outstanding as of December 12, 2025. Management outlines steps taken and planned to improve controls, including hiring qualified personnel, enhancing review and approval processes, restricting system access, and engaging external expertise, while stating that the financial statements still fairly present the company’s results in conformity with GAAP.

Pineapple Financial Inc. reported multiple amendments to its financing and registration agreements tied to a private placement of subscription receipts. The fourth amendment to its Securities Purchase Agreement extends the escrow deadline to 120 days from the closing date and adds governance conditions linked to the Injective Foundation.

Before escrow funds are released, the Company will appoint an additional director nominated by the Injective Foundation and create a three-member Special Advisory Committee to oversee its digital asset treasury strategy and reserve policy, with authority to hire independent and strategic advisors. Separate amendments require Pineapple to file a resale registration statement with the SEC by December 15, 2025 and to have it declared effective no later than the escrow deadline.

Pineapple Financial Inc. (PAPL) files its annual report as a Canadian mortgage technology and brokerage platform centered on its cloud-based MyPineapple system, which supports hundreds of field agents across multiple provinces. Revenue is primarily from lender commissions, with smaller streams from platform subscriptions and pre-underwriting fees.

The company is expanding into insurance through wholly owned subsidiary Pineapple Insurance, officially launched in October 2024 to offer life, critical illness and related products integrated into MyPineapple. Management outlines an organic growth strategy focused on agent recruitment, national expansion and deeper use of analytics.

After year-end, Pineapple entered a US$100 million private placement in subscription receipts funded partly with Injective (INJ) tokens, a US$15 million Voltedge revolving credit facility largely invested in INJ, and a US$250 million equity line with White Lion. A new INJ-focused digital asset treasury and on-chain mortgage R&D introduce significant volatility, regulatory and operational risks highlighted extensively in the risk factors section.

Pineapple Financial Inc. (PAPL) filed an 8-K disclosing amendments to prior financing agreements. The company and a majority of investors signed a Third Amendment to the Securities Purchase Agreement and a First Amendment to the Registration Rights Agreement. These amendments require the company to file a registration statement with the SEC by December 5, 2025 and to seek its effectiveness as soon as possible and not later than the Escrow Deadline.

The original private placement, entered on September 2, 2025 and amended September 4, 2025, involved subscription receipts priced at $3.80 for certain purchasers and $4.16 for others. The updated commitments center on timing for the resale registration rather than changing economic terms.

Pineapple Financial Inc. (PAPL) amended its private placement terms. The company and holders of at least 50.1% of the Subscription Receipts executed a second amendment to the Securities Purchase Agreement. The amendment sets the Escrow Deadline at ninety days from the Closing Date, subject to further extension as described in the amendment.

The private placement involves Subscription Receipts priced at $3.80 for certain purchasers and $4.16 for others. At a special meeting on October 31, 2025, shareholders voted on matters presented, with one item receiving 213,511 votes for, 9,970 against, and 2,148 abstentions, and another showing 215,795 for, 9,468 against, and 366 abstentions.

Pineapple Financial Inc. is asking shareholders at a special meeting to vote on two proposals: a Share Issuance Proposal and a Restriction Removal Proposal. The board recommends shareholders vote FOR both proposals. The definitive proxy excerpt shows beneficial ownership for named directors and officers, with all directors and officers as a group holding 338,784 shares (25.14%). The document includes voting logistics (how to vote, changing a proxy, quorum and vote tabulation) and is signed by Shubha Dasgupta, Chief Executive Officer on September 29, 2025.