Core Viewpoint - Pineapple Financial Inc. has issued a statement addressing recent unusual trading activity, confirming no material developments beyond previously disclosed information [1][2]. Group 1: Company Response - The company conducted an internal review and found no new material developments in its business [1]. - Pineapple Financial emphasizes reliance on official filings and press releases for updates [1]. - The recent Form 8-K filing highlighted an improved cash position and ongoing execution of its strategic plan [2]. Group 2: Company Overview - Pineapple Financial is a leading Canadian mortgage brokerage network and fintech company, focusing on the success of agents and brokers as well as enhancing the homeowner experience [3]. - The company utilizes advanced cloud-based tools and AI-driven systems to assist brokers in helping Canadians achieve homeownership [3]. - Pineapple is actively involved in community support, sponsoring charities across Canada to improve lives [3].

Pineapple Financial Announces Relisting on the NYSE AmericanMilestone marks renewed growth strategy, increased accessibility for investors, and operational momentumJuly 17, 2025 8:00 AM EDT | Source: Pineapple Financial Inc.Toronto, Ontario--(Newsfile Corp. - July 17, 2025) - Pineapple Financial Inc. (NYSE American: PAPL), a leading Canadian mortgage technology and brokerage company, today announced that it has successfully completed a 1-for-20 reverse stock split and has been approved for rel ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended May 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-41738 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in its charter) Canada Not applicable (State or other jurisdiction of i ...

Core Viewpoint - Pineapple Financial Inc. has successfully closed a public offering, raising gross proceeds of $1,500,000 through the sale of 10,000,000 units at a price of $0.15 per unit, each unit consisting of one common share and one warrant [1][3]. Group 1: Offering Details - The public offering consisted of 10,000,000 units priced at $0.15 each, resulting in total gross proceeds of $1,500,000 before fees and expenses [1]. - The offering was conducted under an effective registration statement filed with the SEC, which was declared effective on May 1, 2025 [3]. - D. Boral Capital LLC served as the exclusive placement agent for the offering, while legal counsel was provided by Sichenzia Ross Ference Carmel LLP for the Company and Lucosky Brookman LLP for D. Boral Capital LLC [2]. Group 2: Company Overview - Pineapple Financial Inc. is a prominent Canadian mortgage technology and brokerage firm, focused on enhancing the mortgage experience for brokers, lenders, and clients [5]. - The company offers advanced tools, marketing automation, analytics, and proprietary technology aimed at simplifying the mortgage process [5]. - Pineapple is committed to innovation and aims to set a new standard for excellence within the mortgage industry [5].

Core Viewpoint - Pineapple Financial Inc. has announced a public offering of 10,000,000 units at a price of $0.15 per unit, each unit consisting of one share of common stock and one warrant to purchase an additional share [1][2]. Group 1: Offering Details - The offering is expected to close on or about May 5, 2025, subject to customary closing conditions [2]. - D. Boral Capital LLC is acting as the Exclusive Placement Agent for the offering [2]. - The offering is conducted under the Company's registration statement on Form S-1, which was declared effective by the SEC on May 1, 2025 [3]. Group 2: Company Overview - Pineapple Financial Inc. is a leading Canadian mortgage technology and brokerage firm focused on enhancing the mortgage process for brokers, lenders, and clients [5]. - The company provides advanced tools, marketing automation, analytics, and proprietary technology aimed at simplifying the mortgage experience [5]. - Pineapple is committed to innovation and aims to set a new standard for excellence in the mortgage industry [5].

Financial Performance - The company originated $690.002 million in residential mortgage loans during the six-month period ended February 28, 2025, representing a 17.61% increase compared to $568.521 million in the same period the previous year [91]. - The net loss for the period was $1.166 million, an improvement of 24.33% from a net loss of $1.541 million in the six months ended February 29, 2024 [92]. - Gross billing revenue increased to $9.33 million, up 15.23% from $8.09 million for the same period in the prior year [107]. - Revenue for the period increased to $1.51 million, representing an 11.78% increase year-over-year from $1.35 million [109]. - The net loss for the period was $1,253,990, compared to $1,530,696 in the six months ended February 29, 2024, indicating improved operational scaling while investing in revenue-generating activities [147]. Expenses and Costs - Commission expense rose to $7.81 million, reflecting a 15.92% increase from $6.74 million in the prior-year period [108]. - Operating expenses decreased by 3.48% to $2.81 million compared to $2.91 million in the previous year [105]. - The company experienced a significant increase in interest expense and bank charges, rising by 448.93% to $273,812 [105]. - Commission expense rose by 20.40% to $3.78 million, attributed to reliance on high-volume agents [113]. - Selling, general, and administrative expenses totaled $995,190, representing a 3.56% decrease compared to the prior year [117]. - Software subscription expenses increased by $47,556 (11.82%) to $449,845, reflecting ongoing investment in digital infrastructure [118]. - Interest expense and bank charges surged by 448.93% to $273,812, primarily due to higher borrowing costs [139]. - Depreciation expense rose by 36.32% to $429,645, driven by investments in proprietary technology [140]. - Dues and subscription expenses increased by 163.50% to $164,917, reflecting expanded access to industry platforms [131]. - Travel expenses declined by 96.63% to $2,925, attributed to cost control measures and a shift to virtual collaboration [134]. - Government incentive income decreased by 39.60% to $48,518, due to the transition to public company status [141]. Cash Flow and Liquidity - For the six-month period ended February 28, 2025, net cash used in operating activities was $836,228, a significant improvement from $1,566,642 in the prior-year period, reflecting enhanced operational efficiencies and disciplined working capital management [146][149]. - Net cash provided by financing activities amounted to $1,226,321, down from $2,751,937 in the same period of the prior year, attributed to reduced financing proceeds despite continued access to capital [150]. - As of February 28, 2025, the Company had cash and cash equivalents of $493,607, a decrease from $1,339,618 at the end of the same period last year, primarily due to investments in technology and working capital [153]. - Management remains focused on maintaining sufficient liquidity to support operational needs and strategic priorities, evaluating opportunities for both non-dilutive and equity-based financing [154]. Investments and Acquisitions - The Company invested in MCommercial, acquiring 5% of the total issued shares, enhancing product offerings and service levels for residential mortgage agents [169]. - The Company also acquired 5% of the total issued shares of Mortgage Alliance Corporation, expanding its presence in the mortgage brokerage sector [170]. - The total value of both investments was recorded at fair value, with any impairment loss recognized in the profit and loss account [171]. Foreign Exchange and Financial Instruments - The company reported a foreign exchange gain of $4,021, compared to a loss of $12,685 in the previous period, reflecting favorable currency fluctuations [150]. - The fair value of cash is categorized as Level 1 at $493,607, while investments are categorized as Level 3 at $9,365 [185]. - The company does not face interest rate risk as it has no variable-rate loans or borrowings [188]. Shareholder and Stock Information - A 1-for-3.9 reverse stock split was completed on July 6, 2023, retroactively adjusting all share numbers and prices [177]. - The company has established a share option plan to attract and retain qualified personnel, reserving 10% of issued common shares for grants [175]. - Stock options granted on June 14, 2021, had a fair value of $1,317,155 and were fully vested by August 31, 2023 [176]. Internal Controls and Operational Improvements - The company is enhancing its internal controls, including hiring skilled staff and establishing approval processes for transactions [178]. - The company is focused on enhancing profitability through selective onboarding of high-margin agents and reallocating resources to more profitable channels [109]. Receivables and Trade Information - Trade and other receivables as of February 28, 2025, amounted to $177,781, compared to $155,224 on August 31, 2024 [192]. - The company has $57,750 in trade receivables that are greater than 90 days outstanding as of February 28, 2025, up from $36,740 on February 29, 2024 [190].

Financial Performance - The company generated $424.076 million in residential mortgage loans for the three months ending November 30, 2024, reflecting a 9.64% increase from $386.777 million in the same period of 2023[96]. - Gross billing revenue increased by 5.05% from $4.560 million for the three-month period ending November 30, 2023, to $4.791 million for the same period in 2024[108]. - Revenue for the three-month period ending November 30, 2024, rose to $766,074, a 34.55% increase from $569,355 in the same period of 2023, driven by a strategic focus on high-margin agents[109]. - The company's net loss decreased to $0.657 million for the three months ending November 30, 2024, compared to a loss of $0.898 million in the corresponding period of 2023[96]. - Net cash used in operating activities decreased to $663,597, compared to $1,022,782 in the prior period[126]. - Revenue for the year saw a notable increase, reflecting the Company's ability to attract new clients and retain existing ones[127]. Expenses and Cost Management - Selling, general, and administrative expenses decreased by 25.48%, from $560,151 for the three months ending November 30, 2023, to $417,406 for the same period in 2024[111]. - Software subscription expenses increased by 21.55%, from $180,920 during the three months ended November 30, 2023, to $219,908 during the same period in 2024[112]. - Dues and subscriptions decreased by $8,431 (21.06%), from $40,031 during the three months ended November 30, 2023, to $31,600 during the three months ended November 30, 2024[115]. - Consulting fees saw a significant reduction of $156,634 (94.18%), decreasing from $166,313 to $9,679 during the same period[116]. - Travel expenses declined by $18,588 (47.45%), from $39,177 to $20,589[117]. - Advertising and marketing expenses increased by $139,539 (104.55%), rising from $133,470 to $273,009[119]. - Salaries, wages, and benefits fell by $207,908 (32.27%), from $644,273 to $436,365[120]. Market and Operational Insights - The mortgage origination market remains constrained compared to pre-2022 levels, despite signs of recovery due to renewed consumer confidence[95]. - Approximately 40% of the deals originated by users utilized the expert risk pre-assessment service, which is aimed at increasing deal volume and improving service offerings[101]. - The underwriting revenue for the three-month period ending November 30, 2024, was $27,343, down from $42,106 in the same period of 2023[98]. - The company experienced a significant rise in interest expense and bank charges, increasing by 715.18% to $174,505 for the three months ending November 30, 2024[107]. Investments and Acquisitions - The Company raised $1.00 million through the issuance of shares and secured a short-term loan of $525,000 during the three months ended November 30, 2024[128][129]. - The Company allocated $282,298 toward the development of proprietary software aimed at enhancing mortgage application processing efficiency[130]. - The company invested in MCommercial, acquiring 5% of total issued shares, enhancing product offerings and corporate revenue through increased transactions[149]. - The company entered a share purchase agreement to acquire 5% of Alliance, a mortgage brokerage firm, expanding its presence in Ontario and other Canadian cities[150]. Financial Position and Risk Management - As of November 30, 2024, the Company's cash balance stood at $619,581, a decrease from $2,341,537 as of November 30, 2023[131]. - As of November 30, 2024, cash holdings increased to $619,581 from $580,356 on August 31, 2024, while trade and other receivables rose to $182,526 from $155,224[172]. - As of November 30, 2024, $37,800 of trade receivables were over 90 days outstanding, a significant increase from $2,572 on November 30, 2023, indicating rising credit risk[170]. - The company faces credit risk primarily from trade receivables, with maximum exposure approximating the carrying value of assets on the consolidated statements[171]. - The company has no exposure to interest rate risk as it does not have variable-rate loans or borrowings[168]. Corporate Governance and Internal Controls - The company has initiated steps to enhance internal controls, including hiring skilled staff and establishing approval processes for transactions[158][160]. - The fair value of stock options granted was $1,317,155, fully vested by August 31, 2023, with a share option plan reserving 10% of common shares for grants[156][155]. - The company completed a 1-for-3.9 reverse stock split on July 6, 2023, retroactively adjusting share numbers and prices in financial statements[157].

Core Findings - PineappleONE platform adoption led to a 22.72% increase in loan origination, reaching $377 million in Q3 fiscal 2024 [1][3] - Brokers using PineappleONE experienced a 32% reduction in deal processing time due to advanced automation features [3] - Revenue increased by 20.43% in Q3 fiscal 2024, reaching $736,448 compared to $603,231 in the same period last year [4] Efficiency and Revenue Growth - Brokers fully adopting PineappleONE saw individual loan volumes increase by an average of 28% [6] - Top-performing brokers reported a 37.5% reduction in time spent per transaction [6] - Increased efficiency led to higher client satisfaction, referral rates, and repeat business [6] Platform Features and Impact - PineappleONE's automation capabilities include document management, automated lender submissions, and real-time client updates [4] - The platform has set a new standard in the mortgage industry by enhancing broker productivity and client outcomes [7] Future Plans and Innovation - Pineapple Financial plans to introduce AI-driven tools to optimize lead management and client retention [8] - The company aims to further enhance PineappleONE with additional features to increase automation and broker support [8] Company Overview - Pineapple Financial Inc is a leading Canadian fintech company with approximately 700 brokers in its network [9] - The company focuses on creating cutting-edge cloud-based tools and AI-driven systems to support brokers and homeowners [9]

Core Insights - Pineapple Financial Inc. has expanded its affiliate network by adding six new mortgage brokerages in Ontario, Canada, enhancing its market reach and service capabilities [1][2][5] - The affiliate network accounted for 36.8% of Pineapple's total funded volume and revenue in the 2023 fiscal year, indicating a significant contribution to the company's financial performance [2] - The company aims to leverage AI-driven technology to streamline mortgage processes and deliver personalized solutions to clients [5][6] Company Overview - Pineapple Financial is a tech-focused mortgage brokerage with a network of approximately 700 brokers across Canada, emphasizing long-term success for agents and brokerages [7] - The company provides a platform that allows mortgage brokers to operate independently or as affiliate partners, thus retaining their brand while accessing Pineapple's tools and services [1][2] New Affiliates - The six new brokerages joining the network are CRE Capital Canada, Top Notch Financial, Tailored Finance Inc., PrimeRock Capital Corp., Reign Mortgage Group Inc., and Newcastle Financial, each bringing expertise in serving clients' mortgage needs [3][4][8] - The addition of these brokerages is expected to drive significant growth in revenue and volume for Pineapple in 2024 [2][6]

Financial Performance - Mortgage volume increased to $314.96 million for the three months ended February 29, 2024, compared to $267.90 million for the same period in 2023, representing a 17.55% increase[13] - Net sales revenue rose to $343,305 for the three months ended February 29, 2024, from $207,081 in the same period last year, marking a significant increase of 65.96%[13] - Total revenue, net for the six months ended February 29, 2024, was $1.35 million, a slight increase of 1.36% from $1.33 million for the same period in 2023[15] - Sales revenue decreased from $8.46 million in the six months ending February 28, 2023, to $8.09 million in the six months ending February 29, 2024, representing a 4.39% decline[22] - The company experienced a net loss attributable to Pineapple Financial of $(1.53) million for the six months ended February 29, 2024, compared to a net loss of $(1.40) million for the same period in 2023[16] - The company’s adjusted EBITDA for the six months ended February 29, 2024, was $(1.11) million, compared to $(67,185) for the same period in 2023[16] Expenses and Cost Management - General and administrative expenses decreased by $72,135 from $1,104,082 during the six months ending February 28, 2023, to $1,031,947 during the six months ending February 29, 2024, a decrease of 6.53%[27] - Salaries, wages, and benefits decreased to $1.19 million for the six months ended February 29, 2024, from $1.27 million for the same period in 2023, reflecting a 6.92% reduction[31] - Advertising and marketing expenses decreased to $404,017 during the six months ending February 29, 2024, compared to $469,321 during the previous six months, a decrease of 13.92%[30] - Stock-based compensation expense was recognized as $0 for the six months ended February 29, 2024, compared to $33,041 for the same period in 2023[53] Cash and Liquidity - As of February 29, 2024, the cash balance was $1,339,618, a significant increase from $79,976 on February 28, 2023[40] - The Company has a liquidity position of $1.340 million in cash and cash equivalents, but liquidity is under pressure due to operational expansion and technology investments[41] - As of February 29, 2024, the Company reported total cash of $1,339,618 and an investment valued at $9,984 under Level 3 fair value measurements[63] Investments and Shareholder Actions - The Company issued 875,000 shares through an initial public offering at $4.00, receiving $2.752 million after expenses[39] - The Company invested in a commercial mortgage firm, MCommercial, representing 5% of total issued shares, enhancing product offerings and revenue potential[49] - A 1-for-3.9 reverse stock split was completed on July 6, 2023, retroactively adjusting share numbers and prices[55] Internal Controls and Compliance - The Company is implementing plans to improve internal controls over financial reporting due to identified deficiencies[56] - Dues and subscriptions increased from $118,568 during the six months ended February 28, 2023, to $152,441 for the six months ended February 29, 2024, representing a 28.57% increase[25]