Pineapple Financial Inc. 10-Q

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 00-0000000 (State or other jurisdiction of incorporation or organization) (I.R.S. Employer Identification No.) Unit 200 , 111 Gordon Baker Road North York , Ontario M2H 3R1 (Address of principal executive offices) (Zip Code) Registrant’s telephone number, including area code: (416) 669-2046 Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. Yes ☒ No ☐ Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§ 232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files). Yes ☒ No ☐. Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act. Large accelerated filer ☐ Accelerated Filer ☐ Non-accelerated filer ☒ Smaller reporting company ☒ Emerging Growth Company ☒ If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐ Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act) Yes ☐ No ☒ Securities registered pursuant to Section 12(b) of the Act: Title of each class Trading symbol Name of each exchange on which registered Common Shares, no par value PAPL NYSE American The number of shares of the registrant’s common stock issued and outstanding, as of July 14, 2025 was 20,092,025 . PINEAPPLE FINANCIAL INC. TABLE OF CONTENTS FOR FORM 10-Q PART I. FINANCIAL INFORMATION Item 1. Financial Statements 2 Consolidated Balance Sheets (unaudited) 3 Consolidated Statements of Operations and Comprehensive Loss(unaudited) 4 Consolidated Statements of Shareholders’ Equity (unaudited) 5 Consolidated Statements of Cash Flows (unaudited) 6 Notes to Consolidated Financial Statements (unaudited) 7 Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations 21 Item 3. Quantitative and Qualitative Disclosures About Market Risk 34 Item 4. Controls and Procedures 34 PART II. OTHER INFORMATION Item 1. Legal Proceedings 34 Item 1A. Risk Factors 34 Item 2. Unregistered Sales of Equity Securities and Use of Proceeds 34 Item 3. Defaults Upon Senior Securities 35 Item 4. Mine Safety Disclosures 35 Item 5. Other Information 35 Item 6. Exhibits 35 SIGNATURES 36 i FORWARD-LOOKING STATEMENTS This report contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, or the “Securities Act,” and Section 21E of the Securities Exchange Act of 1934 or the “Exchange Act.” These forward-looking statements are subject to certain risks and uncertainties that could cause actual results to differ materially from historical results or anticipated results. In some cases, you can identify forward-looking statements by terms such as “may,” “intend,” “might,” “will,” “should,” “could,” “would,” “expect,” “believe,” “anticipate,” “estimate,” “predict,” “potential,” or the negative of these terms. These terms and similar expressions are intended to identify forward-looking statements. The forward-looking statements in this report are based upon management’s current expectations and beliefs, which management believes are reasonable. In addition, we cannot assess the impact of each factor on our business or the extent to which any factor or combination of factors, or factors we are aware of, may cause actual results to differ materially from those contained in any forward-looking statements. You are cautioned not to place undue reliance on any forward-looking statements. These statements represent our estimates and assumptions only as of the date of this report. Except to the extent required by federal securities laws, we undertake no obligation to update any forward-looking statement to reflect events or circumstances after the date hereof or to reflect the occurrence of unanticipated events. You should be aware that our actual results could differ materially from those contained in the forward-looking statements due to a number of factors, including: ● the timing of the development of future services, ● projections of revenue, earnings, capital structure and other financial items, ● statements regarding the capabilities of our business operations, ● statements of expected future economic performance, ● statements regarding competition in our market, and ● assumptions underlying statements regarding us or our business. Other risks and uncertainties include such factors, among others, as market acceptance and market demand for our products and services, pricing, the changing regulatory environment, the effect of our accounting policies, industry trends, adequacy of our financial resources to execute our business plan, our ability to attract, retain and motivate key personnel, and other risks described from time to time in periodic and current reports we file with the United States Securities and Exchange Commission, or the “SEC.” You should consider carefully the statements under this report, which address additional factors that could cause our actual results to differ from those set forth in the forward-looking statements and could materially and adversely affect our business, operating results and financial condition. All subsequent written and oral forward-looking statements attributable to us or persons acting on our behalf are expressly qualified in their entirety by the applicable cautionary statements. 1 Pineapple Financial Inc. Condensed Interim Consolidated Financial Statements (Unaudited) For the nine month period ended May 31, 2025 (Expressed in US Dollars) 2 Pineapple Financial Inc. Condensed Interim Consolidated Balance Sheets - Unaudited (Expressed in US Dollars) As at: May 31, 2025 August 31, 2024 Assets Current assets Cash $ 1,134,583 $ 580,356 Trade and other receivables Note 13 180,462 155,224 Prepaid expenses and deposits 81,821 157,911 Total current assets 1,396,866 893,491 Investment Note 4 9,847 10,042 Right-of-use asset Note 10 656,070 828,674 Property and equipment Note 5 84,570 152,610 Intangible assets Note 6 2,555,050 2,211,775 Total Assets $ 4,702,403 $ 4,096,592 Liabilities and Shareholders’ Equity Current liabilities Accounts payable and accrued liabilities $ 1,462,844 $ 1,125,477 Deferred revenue 151,328 111,921 Short term loan Note 17 633,259 - Current portion of lease liability Note 10 166,355 161,508 Total current liabilities 2,413,786 1,398,906 Deferred government incentive Note 13 410,087 491,251 Lease liability Note 10 672,622 815,599 Warrant liability Note 8 363,343 41,520 Total liabilities $ 3,859,838 $ 2,747,276 Shareholders’ Equity Common shares, no par value; unlimited authorized; 20,092,025 issued and outstanding shares as of May 31, 2025 and 8,425,358 as at August 31, 2024. Note 7 9,920,070 8,559,856 Additional paid-in capital Note 8,9 2,955,944 2,955,944 Accumulated other comprehensive loss ( 461,363 ) ( 408,510 ) Accumulated deficit ( 11,572,086 ) ( 9,757,974 ) Total stockholders’ equity 842,565 1,349,316 TOTAL LIABILITIES AND STOCKHOLDERS’ EQUITY $ 4,702,403 $ 4,096,592 Description of business and going concern (note 1) Contingencies and commitments (note 15) Subsequent events (note 18) Approved on behalf of Board of Directors “Shuba Dasgupta” “Drew Green” The accompanying notes are an integral part of these unaudited condensed interim consolidated financial statements 3 Pineapple Financial Inc. Condensed Interim Consolidated Statements of Operations and Comprehensive Loss (Unaudited) For the three month and nine month ended May 31, 2025 (Expressed in US Dollars) May 31, 2025 May 31, 2024 May 31, 2025 May 31, 2024 Three months ended Nine months ended May 31, 2025 May 31, 2024 May 31, 2025 May 31, 2024 For the period ended (Unaudited) (Unaudited) (Unaudited) (Unaudited) Revenue Note 16 $ 746,903 736,448 $ 2,259,396 1,971,377 Expenses Selling, general and administrative Note 11 527,835 491,666 1,522,778 1,545,900 Advertising and Marketing 292,489 265,395 617,987 648,197 Salaries, wages and benefits 394,648 593,202 1,223,722 1,825,786 Interest expense and bank charges 31,216 40,373 306,267 42,825 Depreciation Note 5,6,10 219,355 220,190 648,991 535,575 Share-based compensation Note 9 - - - - Government Incentive Note 13 ( 22,109 ) 21,770 ( 70,657 ) ( 176,326 ) Total expenses $ 1,443,434 1,632,596 $ 4,249,088 4,421,957 Loss from operations ( 696,531 ) ( 896,148 ) ( 1,989,692 ) ( 2,450,580 ) Foreign exchange gain (loss) ( 6,018 ) - ( 1,905 ) 10,751 Gain (loss) on change in fair value of warrant liability Note 8 309,516 29,479 341,765 42,251 Gain (loss) on change in fair value of conversion feature liability - 18,064 - 18,134 Financing costs – warrant issuance ( 164,703 ) - ( 164,280 ) - Loss before income taxes $ ( 557,736 ) ( 848,605 ) $ ( 1,814,112 ) ( 2,379,444 ) Income taxes (recovery) expense - - - - Net loss $ ( 557,736 ) ( 848,605 ) $ ( 1,814,112 ) ( 2,379,444 ) Foreign currency translation adjustment ( 34,703 ) ( 41,676 ) 52,853 ( 62,666 ) Net loss and comprehensive loss $ ( 592,439 ) ( 890,281 ) $ ( 1,761,259 ) ( 2,442,110 ) Loss per share - basic and diluted ($) ( 0.05 ) ( 0.12 ) ( 0.17 ) ( 0.33 ) Weighted average number of common shares outstanding - basic and diluted 12,714,242 7,181,978 10,067,480 7,181,978 Loss per share - basic and diluted ($) (Post reverse split : 20 shares to 1 share) ( 0.93 ) ( 2.48 ) ( 3.50 ) ( 6.80 ) Weighted average number of Common shares outstanding – basis and diluted (Post reverse split: 20 Shares to 1 Share) Note 18 635,712 359,099 503,374 359,0991 The accompanying notes are an integral part of these condensed interim consolidated financial statements 4 Pineapple Financial Inc. Condensed Interim Consolidated Statements of Changes in Shareholders’ Equity - Unaudited (Expressed in US Dollars) Common Shares (note 7) Additional Paid in Capital (note 8 and 9) Accumulated other comprehensive loss Accumulated (deficit) earnings Total shareholders’ equity $ $ $ $ $ Balance, August 31, 2023 4,903,031 2,955,944 ( 417,727 ) ( 5,655,315 ) 1,785,933 Shares issued on Initial Public offering on November 3, 2023 2,751,937 - - - 2,751,937 Warrants issued related to Initial Public Offering ( 48,283 ) - - - ( 48,283 ) Foreign exchange translation - - ( 62,666 ) - ( 62,666 ) Net loss - - - ( 2,379,444 ) ( 2,379,444 ) Balance, May 31, 2024 7,606,685 2,955,944 ( 480,393 ) ( 8,034,759 ) 2,047,477 Shares issued 953,171 - - - 953,171 Foreign exchange translation - - 71,883 - 71,883 Net loss - - - ( 1,723,215 ) ( 1,723,215 ) Balance, August 31, 2024 8,559,856 2,955,944 ( 408,510 ) ( 9,757,974 ) 1,349,316 Balance 8,559,856 2,955,944 ( 408,510 ) ( 9,757,974 ) 1,349,316 Shares issued against S3 731,922 - - - 731,922 Shares issued against FPO 628,292 - - - 628,292 Foreign exchange translation - - ( 52,853 ) - ( 52,853 ) Net loss - - - ( 1,814,112 ) ( 1,814,112 ) Balance, May 31, 2025 9,920,070 2,955,944 ( 461,363 ) ( 11,572,086 ) 842,565 Balance 9,920,070 2,955,944 ( 461,363 ) ( 11,572,086 ) 842,565 The accompanying notes are an integral part of these consolidated unaudited condensed interim financial statements 5 Pineapple Financial Inc. Condensed Interim Consolidated Statements of Cash Flow - Unaudited (Expressed in US Dollars) May 31, 2025 May 31, 2024 Nine Months Ended May 31, 2025 May 31, 2024 For the period ended: (Unaudited) (Unaudited) $ $ Cash provided by (used for) the following activities Operating activities Net loss for the three months ( 1,814,112 ) ( 2,379,444 ) Adjustments for the following non-cash items: Depreciation of property and equipment Note 5 64,201 65,300 Amortization of intangible assets Note 6 430,391 369,993 Depreciation on right of use asset Note 10 154,399 100,282 Interest expense on lease liability Note 10 39,601 47,482 Change in fair value of warrant liability 341,765 ( 42,251 ) Foreign exchange gain (loss) ( 1,905 ) ( 10,751 ) Change in fair value of conversion feature liability Note 18 - ( 18,133 ) Net changes in non-cash working capital balances: Trade and other receivables ( 25,238 ) 607,724 Prepaid expenses and deposits 76,090 65,976 Accounts payable and accrued liabilities 337,367 ( 74,756 ) Deferred government incentive ( 81,164 ) ( 175,032 ) Deferred revenue 39,407 - Net cash used in operating activities ( 439,198 ) ( 1,443,610 ) Financing activities Share capital issuance Note 7 1,360,214 2,751,937 Proceed from loan Note 17 633,259 - Note payable proceed - 300,000 Repayment of loan - ( 430,099 ) Repayment of lease obligations Note 10 ( 157,146 ) ( 141,032 ) Net cash provided by financing activity 1,836,327 2,480,806 Investing activities Additions to intangible assets Note 6 ( 811,443 ) ( 896,223 ) Additions to property and equipment Note 5 - ( 4,962 ) Net cash used in investing activity ( 811,443 ) ( 901,185 ) Net change in cash 585,686 136,011 Effect of changes in foreign exchange rates ( 31,459 ) ( 107,607 ) Cash, beginning of period 580,356 720,365 Cash, end of the period 1,134,583 748,769 The accompanying notes are an integral part of these unaudited condensed interim consolidated financial statements 6 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 1. Description of business Pineapple Financial Inc. (the” Company”) is a leader in the Canadian mortgage industry, breaking the mold by focusing on both the long-term success of agents and brokerages, as well as the overall experience of homeowners. With over 600 brokers within the network, the Company utilizes cutting-edge cloud-based tools and AI-driven systems to enable its brokers to help Canadians realize their ultimate dream, owning a home. The Company was incorporated in 2006 under the Ontario Business Corporations Act. Its head office is located at 200-111 Gordon Baker Road, Toronto, Ontario, M2H 3R1, Canada. The Company completed its Initial Public Offering on October 31, 2023, raising gross proceeds of $ 3,500,000 , and commenced trading on the NYSE American under the ticker symbol “PAPL” on November 1, 2023. Subsequently, the Company received a notice of delisting from the NYSE American due to non-compliance with certain continued listing standards. The Company is currently in the appeal process regarding this delisting. In the interim, the Company’s common shares commenced trading on the OTC Markets under the symbol “PAPLF” (OTCPK). The Company continues to actively pursue its appeal and is evaluating its options with respect to relisting on a national securities exchange. Impact from the global inflationary pressures leading to higher interest rates During the first quarter of 2025, inflationary pressures were eased to a greater extent, and central banks worldwide started decreasing their interest rates. However, interest rates are still high compared to the year 2022. The real estate market has started showing some improvement, but inflation is down from the year 2022 but still not as per target. This led to uncertainty around the business. The Company determined that there were no material expectations of increased credit losses and no material indicators of impairment of long-term assets. Economic and Trade Policy Uncertainty Company continues to monitor the potential impact of evolving trade policies, including the threat of additional tariffs imposed by the United States. While no specific tariffs have been implemented during the reporting period that materially affect the Company’s operations, the potential for future changes in cross-border trade arrangements and import/export duties contributes to broader economic uncertainty. Management has considered these risks in its forward-looking assessments and determined that, as of the reporting date, there are no material adverse effects on the Company’s financial position, results of operations, or estimates related to credit losses or asset impairments. 7 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 1. Description of business (continued from previous page) Going Concern The Company continues to focus its efforts predominantly on research and development activities. During this process, it has incurred significant operating losses, a trend expected to persist for the foreseeable future. As of May 31, 2025, the Company reported an accumulated deficit of $ 11,572,086 compared to $ 9,757,974 as of August 31, 2024. Negative cash flows from operating activities amounted to $ 439,198 during the nine months ended May 31, 2025, as compared to $ 1,443,610 in the prior corresponding period. To sustain its operations during the nine-month period end May 31, 2025, the Company raised grossly $ 2.497 million issuance of common shares, warrants and pre-funded warrants. In addition, company also borrowed short term loan $ 633,259 from directors to meet the working capital requirements. In addition, the Company maintains Equity Line of Credit of up to $ 15.00 million, which it intends to draw upon once its securities are registered with the Ontario Securities Commission. It is also exploring additional capital and financing sources such as director’s loan while managing existing working capital resources. However, the Company’s ability to continue as a going concern is subject to its capacity to achieve future profitability and secure the necessary funding to meet obligations as they arise. The uncertainty surrounding its ability to raise financial capital and generate profitable operations raises substantial doubt about its ability to continue as a going concern. These condensed interim consolidated financial statements do not include adjustments that might be necessary should the Company be unable to continue as a going concern. The consolidated financial statements were authorized for issue by the Board of Directors on July 14, 2025 2. Significant accounting policies Basis of preparation, functional and presentation currency The condensed interim consolidated financial statements have been prepared in accordance with US GAAP applicable to a going concern, which contemplates the realization of assets and the satisfaction of liabilities in the normal course of business on the historical cost basis except for certain financial instruments that are measured at fair value. Historical cost is generally based on the fair value of the consideration given in exchange for assets. All financial information is presented in US Dollars (“USD”) as the Company’s presentation currency and functional currency is in Canadian Dollars (“CAD”). The interim financial statements are condensed and should be read in conjunction with the Company’s latest annual year-end consolidated financial statements for the year ended August 31, 2024. It is management’s opinion that all adjustments necessary for a fair statement of the results for the interim period has been made, and all adjustments are of a recurring nature or a description of the nature of and any amount of any adjustments other than normal recurring nature has been stated. Sufficient disclosures have been so as to not make the interim financial information misleading. There are no prior-period adjustments in these condensed interim consolidated financial statements. Operating segments The Company determines its reporting units in accordance with the Financial Accounting Standards Board (“FASB”) Accounting Standards Codification (“ASC”) 280, Segment Reporting. The Company evaluates a reporting unit by first identifying its operating segments under ASC 280. The Company operates as one operating segment which is reported in a manner consistent with the internal reporting provided to the chief operating decision-makers. The chief operating decision-makers are responsible for the allocation of resources and assessing the performance of the operating segment and have been identified as the CEO and CFO of the Company. 8 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 2. Significant accounting policies (continued from previous page) Basis of consolidation The condensed interim consolidated financial statements include the accounts of the Company, and its wholly owned subsidiary, Pineapple Insurance Inc and Pineapple National Inc. All transactions with the subsidiaries and any intercompany balances, gains or losses have been eliminated upon consolidation. The subsidiaries have a USD presentation currency, and the functional currency is in CAD, and accounting policies have been applied consistently to the subsidiaries. Recently issued and adopted accounting standards : As an “emerging growth company,” the Jumpstart Our Business Startups Act (“JOBS Act”) allows the Company to delay adoption of new or revised accounting pronouncements applicable to public companies until such pronouncements are made applicable to private companies. The Company has elected to use this extended transition period under the JOBS Act. The adoption dates discussed below reflects this election. Recently Adopted In July 2023, the FASB issued 2023-03 — Presentation of Financial Statements (Topic 205), Income Statement — Reporting Comprehensive Income (Topic 220), Distinguishing Liabilities from Equity (Topic 480), Equity (Topic 505), and Compensation — Stock Compensation (Topic 718): Amendments to SEC Paragraphs Pursuant to SEC Staff Accounting Bulletin No. 120, SEC Staff Announcement at the March 24, 2022, EITF Meeting, and Staff Accounting Bulletin Topic 6.B, Accounting Series Release 280 — General Revision of Regulation S-X: Income or Loss Applicable to Common Stock (SEC Update). The adoption of this standard on August 1, 2023, did not result in amended disclosures in the Company’s consolidated financial statements, nor did this standard have a material impact the Company’s results of operations. In March 2024, the FASB issued ASU 2023-07 — Segment Reporting (Topic 280): Improvements to Reportable Segment Disclosures. The update enhances disclosures by requiring entities to provide more detailed information about significant segment expenses, other segment items, and measures of segment profit or loss used by the chief operating decision maker (CODM). The guidance also requires qualitative descriptions of the methods used to determine segment profit/loss and asset measurement. The adoption of this standard did not have a material impact on the Company’s consolidated financial statements but resulted in expanded disclosures within the segment reporting footnotes. Not Yet Adopted In December 2023, the FASB issued ASU 2023-09 - Income Taxes (Topic 740): Improvements to Income Tax Disclosures. This standard modifies the rules on income tax disclosures to require entities to disclose specific categories in the rate reconciliation, the income or loss from continuing operations before income tax expense or benefit, and income tax expense or benefit from continuing operations. ASU 2023-09 also requires entities to disclose their income tax payments to international, federal, state, and local jurisdictions. The ASU is effective for years beginning after December 15, 2024, but early adoption is permitted. This ASU should be applied on a prospective basis, although retrospective application is permitted. The Company is currently evaluating the impact of this standard on its financial statements and disclosures. In March 2024, the FASB issued ASU 2024-01 - Compensation—Stock Compensation (Topic 718): Scope Application of Profits Interest and Similar Awards. This standard clarifies whether profits interest and similar awards fall within the scope of stock-based compensation guidance as defined in ASC Topic 718, introducing examples to demonstrate this. The ASU includes scenarios where profits interest awards are classified as equity instruments or liability awards and situations where they fall outside ASC Topic 718, being accounted for under ASC Topic 710. The ASU is effective for years beginning after December 15, 2024, but early adoption is permitted. This ASU should be applied on a prospective basis, although retrospective application is permitted. The Company is currently evaluating the impact of this standard on its financial statements and disclosures. In November 2024, the FASB issued ASU 2024-03: Income Statement - Reporting Comprehensive Income - Expense Disaggregation Disclosure (Subtopic 220-40) – Disaggregation of Income Statement Expenses. The new guidance requires companies to disclose information about specific expenses at each interim and annual reporting period. The guidance is effective for fiscal years beginning after December 15, 2026 and interim periods with fiscal years beginning after December 15, 2027. The Company is in the process of evaluating the requirements of the update, which may result in expanded disclosures upon adoption. 9 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 3. Significant accounting judgments, estimates and assumptions The preparation of condensed interim consolidated financial statements requires the directors and management to make judgments, estimates and assumptions that affect the application of policies and reported amounts of assets and liabilities, and revenue and expenses. Actual results may differ from these estimates. The estimates and underlying assumptions are reviewed on an ongoing basis. Revisions to accounting estimates are recognized in the period in which the estimate is revised if the revision affects only that period or in the period of the revision and future periods if the revision affects both current and future periods. The following are the critical estimates and judgments applied by management that most significantly affect the Company’s condensed interim consolidated financial statements. Uncertainty about these assumptions and estimates could result in outcomes that require a material adjustment to the carrying amount of assets or liabilities affected in future periods. Investments (level 3) Where the fair values of financial assets and financial liabilities recorded on the condensed interim consolidated statements of financial position, cannot be derived from active markets, they are determined using a variety of valuation techniques. The inputs to these models are derived from observable market data where possible; where observable market data is not available, Management’s judgment is required to establish fair values. Share based compensation Management is required to make certain estimates when determining the fair value of stock options awards, and the number of awards that are expected to vest. These estimates affect the amount recognized as stock-based compensation in the statements of income and comprehensive income based on estimates of volatility, forfeitures and expected lives of the underlying stock options which are at a maximum of 36 months vesting period. Warrant Liability: The Company accounts for warrants as either equity-classified or liability-classified instruments based on an assessment of the warrant’s specific terms and applicable authoritative guidance in ASC 480 and ASC 815. The assessment considers whether the warrants are freestanding financial instruments pursuant to ASC 480, meet the definition of a liability pursuant to ASC 480, and whether the warrants meet all of the requirements for equity classification under ASC 815, including whether the warrants are indexed to the Company’s own ordinary shares, among other conditions for equity classification. This assessment, which requires the use of professional judgment, is conducted at the time of warrant issuance and as of each subsequent quarterly period end date while the warrants are outstanding. For issued or modified warrants that meet all of the criteria for equity classification, the warrants are required to be recorded as a component of additional paid-in capital at the time of issuance. For issued or modified warrants that do not meet all the criteria for equity classification, the warrants are required to be recorded as liabilities at their initial fair value on the date of issuance, and each balance sheet date thereafter. Changes in the estimated fair value of the warrants are recognized as a non-cash gain or loss on the consolidated statements of operations and comprehensive loss. The warrants are not precluded from equity classification and are accounted for as such on the date of issuance and will be on each consolidated balance sheet date thereafter. As the warrants are equity classified, they are initially measured at fair value (or allocated value). Derivative Financial Instrument: The Company evaluates its financial instruments to determine if such instruments are derivatives or contain features that qualify as embedded derivatives in accordance with ASC Topic 815, Derivatives and Hedging (“ASC 815”). For derivative financial instruments that are accounted for as liabilities, the derivative instrument is initially recorded at its fair value on the grant date and is then re-valued at each reporting date, with changes in the fair value reported in the consolidated statements of operations and comprehensive loss. For derivative instruments that are classified as equity, the derivative instruments are initially measured at fair value (or allocated value), and subsequent changes in fair value are not recognized as long as the contracts continue to be classified in equity. Impairment of long-lived assets Property, plant and equipment and intangible assets are reviewed for impairment whenever events or changes in circumstances indicate that the carrying amount of such assets may not recoverable. Judgement is involved in identifying events and changes in circumstances. Going Concern Preparation of the condensed interim consolidated financial statement on a going concern basis, which contemplates the realization of assets and payments of liabilities in the ordinary course of business. Should the Company be unable to continue as a going concern, it may be unable to realize the carrying value of its assets, including its intangible assets and to meet its liabilities as they become due. 10 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 3. Significant accounting judgments, estimates and assumptions (continued) Useful life of Assets Significant judgement is involved in determination of useful life for the property plant and equipment and intangible assets. Management assesses the reasonability of the useful life on an annual basis to record the depreciation of the intangibles and property plant and equipment. The intangible assets were initially assigned a useful life of 5 years. However, in June 2024, based on a reassessment of the software’s expected utility, the Company revised its estimate of the useful life to 7 years. 4. Investment During the year ended August 31, 2021, the Company purchased an investment in a private company. The Company holds a 5 % interest with no significant influence. The investment is recorded at FVTPL using level 3 inputs. As at May 31, 2025, the Company recognized a $ Nil change in fair value (2024- $ Nil ). Change in fair value during the current period is due to foreign exchange translation. 5. Property and equipment The Company’s property and equipment consist of equipment, furniture, IT equipment, leasehold improvements and laptops. Schedule of property and equipment Property and equipment Cost Balance, August 31, 2023 $ 349,283 Additions 4,991 Translation adjustment 569 Balance, August 31, 2024 $ 355,576 Translation adjustment ( 6,908 ) Balance, May 31, 2025 $ 348,668 Accumulated depreciation Balance, August 31, 2023 $ 107,192 Depreciation 87,803 Translation adjustment 7,971 Balance, August 31, 2024 $ 202,966 Depreciation 64,201 Translation adjustment ( 3,069 ) Balance, May 31, 2025 $ 264,098 Net carrying value May 31, 2025 $ 84,570 August 31, 2024 $ 152,610 11 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 6. Intangible assets During the current period, the Company capitalized development costs related to internally generated software classified as intangible assets. Schedule of cost and accumulated depreciation Intangible assets Cost Balance, August 31, 2023 $ 2,057,525 Additions 1,112,399 Translation adjustment ( 1,794 ) Balance, August 31, 2024 $ 3,168,130 Additions 811,443 Translation adjustment ( 50,493 ) Balance, May 31, 2025 $ 3,929,080 Accumulated amortization Balance, August 31, 2023 $ 338,571 Amortization 616,532 Translation adjustment 1,252 Balance, August 31, 2024 $ 956,355 Amortization 430,391 Translation adjustment ( 12,716 ) Balance, May 31, 2025 $ 1,374,030 Net carrying value May 31, 2025 $ 2,555,050 August 31, 2024 $ 2,211,775 12 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 7. Share capital Authorized share capital The authorized share capital of the Company consists of an unlimited number of common shares with no par value. Schedule of authorized share capital # $ Balance, August 31, 2023 6,306,984 4,903,031 Issuance of Common Shares on Initial Public Offering 875,000 3,500,000 Issuance of Common Share against Conversion Note 501,875 465,680 Issuance of Common Shares on Equity Purchase Agreement 741,499 487,491 Share Issuance Costs - ( 748,063 ) Warrants issued - ( 48,283 ) Balance, August 31, 2024 8,425,358 8,559,856 Issuance of Common Shares against S3 382,667 232,708 Issuance of Common Shares against Pre-funded warrants 1,284,000 780,769 Issuance of Common Shares against FPO 10,000,000 834,000 Shares Issuance Costs - ( 487,263 ) 11,666,667 1,360,214 Balance, May 31, 2025 20,092,025 9,920,070 During the nine months ended May 31, 2025, the Company issued 382,667 common shares under its Form S-3 shelf registration and 10.00 million common shares under Follow-up Public Offering (FPO). The gross proceeds received from the issuance of the pre-funded warrants were initially recorded within additional paid-in capital before it was exercised. During the period, 1,284,000 pre-funded warrants were exercised, resulting in the issuance of 1,284,000 common shares. 13 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 8. Warrants a) Common Share purchase warrant Schedule of common share purchase warrant # Balance, August 31, 2024 1,652,988 Warrants issued against FPO 10,000,000 Balance, May 31, 2025 11,652,988 b) Pre-funded warrant Schedule of pre-funded warrant Pre-funded warrant issued November 13, 2024 1,284,000 563,824 Shares exercised ( 1,284,000 ) ( 563,824 ) Balance, May 31, 2025 - - The purchase price of each Pre-Funded Warrant is $ 0.5999 , which is equal to the price per share at which the Shares are being sold, minus $ 0.0001 , the exercise price of each Pre-Funded Warrant. During the period, 1,284,000 pre-funded warrants were exercised and converted into the common shares of the Company. c) Warrant Liability On November 3, 2023, the Company issued 26,250 warrants at an exercise price of $ 4 with an expiry date of October 31, 2028 . On May 10, 2024 the Company entered into a convertible debt transaction and issued 1,000,000 warrants at an exercise price of $ 5 with an expiry date of February 10, 2025 . These warrants expired on February 9, 2025. On May 7, 2025 the Company issued 10.00 million warrants at an exercise price of $ 0.15 with an expiry date of May 06, 2030 . As per ASC 815 these instruments did not meet the criteria to be classified as equity instruments as such were classified as financial liabilities. Below is the continuity of the warrant liability valuation. The warrants issued on November 3, 2023 were valued using the Black-Scholes method with the share price of $ 0.04 , exercise price of $ 4 , term of 3.42 years, risk free rate of 2.55 % and volatility of 170.38 % at issuance as at May 31, 2025. The warrants issued on May 07, 2025 were valued using the Black-Scholes method with the share price of $ 0.04 , exercise price of $ 0.15 , term of 4.75 years, risk free rate of 3.95 % and volatility of 170.38 % at issuance as at May 31, 2025. Schedule of warrant liability # $ Balance at August 31, 2024 1,026,250 41,520 Warrants expired ( 1,000,000 ) ( 1,455 ) Warrants issued 10,000,000 666,000 Change in fair value of warrant liability ( 341,765 ) Translation adjustment ( 957 ) Fair Value of Warrants at May 31, 2025 10,026,250 363,343 As at May 31, 2025 the warrants have no intrinsic value (August 31, 2024 – nil ). 14 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 9. Share-based benefits reserve The Company has a share option plan (the “Plan”) to attract, retain and motivate qualified directors, officers, employees and consultants whose present and future contributions are important to the success of the Company by offering them an opportunity to participate in the Company’s future performance through the award of share options. Each share option converts into one common share of the Company on exercise. No amounts are paid or payable by the recipient on receipt of the option. The options carry neither rights to dividends nor voting rights. Options may be exercised at any time from the date of vesting to the date of their expiry. In 2017, the Plan was amended such that the total number of common shares reserved and available for grant and issuance pursuant to the Plan is to equal 10 % of the issued and outstanding common shares of the Company. Options granted on June 14, 2021, vest over a 2-year period whereby 25% of the options granted vested on the date of grant, and the remaining unvested options vest in equal instalments every 6-months thereafter . The fair value of stock options granted was $ 1,317,155 . A total stock-based compensation expense was recognized of $ Nil for the nine months period ended May 31, 2025 (August 31, 2024 - $ Nil ). The following reconciles the options outstanding at the beginning and end of the period that were granted to eligible participants pursuant to the Plan: Schedule of options outstanding granted May 31, 2025 August 31, 2024 Number of Options Weighted Average Exercise Price Number of Options Weighted Average Exercise Price # $ # $ Balance, beginning of period 565,689 3.61 565,689 3.72 Forfeited during the period - - - - Balance as at period end 565,689 3.61 565,689 3.61 Exercisable as at period end 565,689 3.61 565,689 3.61 As at May 31, 2025, the options have no intrinsic value (August 31, 2024 – nil ). As at May 31, 2025, all options are exercisable with a weighted average remaining life of 1.10 years (August 31, 2024 – 1.8 years) 15 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 10. Right-of-use asset and lease liability The Company leases all its office premises in Ontario and British Columbia, Canada. The total lease area is 13,262 sq. ft. The Company acquired a 1,454 square feet premise lease in British Columbia commencing August 1, 2023 and expiring on July 31, 2028. The Company recognized a right-of-use asset and corresponding lease liability in respect of this lease. The lease liability was measured at the present value of the remaining lease payments, discounted using the Company’s estimated incremental borrowing rate as at September 1, 2017 (date of initial application), estimated to be 6%. The right-of-use asset was measured at an amount equal to the lease liability, adjusted by the amount of any prepaid or accrued lease payments relating to that lease recognized in the balance sheet immediately before the date of initial application. The following schedule shows the movement in the Company’s right-of-use asset: Schedule of right-of-use asset Right-of-use asset Cost Balance, August 31, 2023 $ 1,177,721 Translation adjustment ( 42,737 ) Balance, August 31, 2024 1,134,984 Translation adjustment ( 15,686 ) Balance, May 31, 2025 $ 1,119,298 The right-of-use asset is being depreciated on a straight-line basis over the remaining lease term. Accumulated Depreciation Balance, August 31, 2023 $ 217,344 Depreciation 134,508 Translation adjustment ( 45,542 ) Balance, August 31, 2024 $ 306,310 Depreciation 154,399 Translation adjustment 2,519 Balance, May 31, 2025 $ 463,228 Carrying Amount May 31, 2025 $ 656,070 August 31, 2024 $ 828,674 16 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 10. Right-of-use asset and lease liability (continued) The following schedule shows the movement in the Company’s lease liability during the period: Schedule of lease liability May 31, 2025 August 31, 2024 Balance, beginning of period $ 977,107 $ 1,107,961 Interest Expense 39,601 62,604 Lease payments ( 157,146 ) ( 196,703 ) Translation Adjustment ( 20,583 ) 3,245 Balance, end of period $ 838,977 $ 977,107 Current 166,355 161,508 Non-Current 672,622 815,599 $ 838,977 $ 977,107 The following table provides a maturity analysis of the Company’s lease liability. The amounts disclosed in the maturity analysis are the contractual undiscounted cash flows before deducting interest or finance charges: Schedule of maturity lease liability 2025 209,895 2026 211,251 2027 211,315 2028 221,088 2029 197,201 2030 82,167 Total Lease liability $ 1,132,917 17 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 11. Expenses The following table provides a breakdown of the selling, general and administrative: Schedule of selling, general and administrative expenses May 31, 2025 May 31, 2024 Nine months ended May 31, 2025 May 31, 2024 $ $ Software Subscription 624,587 663,424 Office and general 114,864 117,213 Professional fees 108,359 157,531 Dues and Subscriptions 364,287 146,964 Rent 140,168 155,628 Consulting fees 45,483 45,167 Travel 25,467 137,940 Donations 789 7,406 Lease expense 507 54,946 Insurance 98,267 59,681 Selling, general and administrative 1,522,778 1,545,900 May 31, 2025 May 31, 2024 Three months ended May 31, 2025 May 31, 2024 $ $ Software Subscription 174,116 260,951 Office and general 31,170 61,515 Professional fees 47,866 11,871 Dues and Subscriptions 165,688 ( 5,149 ) Rent 54,997 57,528 Consulting fees 15,888 20,663 Travel 2,108 51,867 Donations - 2,759 Insurance 36,002 29,661 Selling, general and administrative 527,835 491,666 12. Related party transactions and balances Compensation of key management personnel includes the CEO, COO, CSO, and CFO: Schedule of related party transactions May 31, 2025 May 31, 2024 $ $ Salaries, Wages and benefits 382,151 554,828 Un-secured loans received from directors are disclosed in Note 17. 18 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 13. Deferred government incentive The Company was eligible for the Government of Canada Scientific Research and Experimental Development (SRED) program up to November 3, 2023. The Company has accrued $ 86,937 of SRED receivable as at May 31, 2025, which is recognized in trades and other receivables in the condensed interim consolidated balance sheet. A portion of the funds received is related to costs that have been capitalized for the development of internally generated software recognized as intangible asset in Note 6. As at May 31, 2025 $ 70,657 (May 31, 2024 $ 176,326 ) was recognized as recovery of operating expenses in the condensed interim consolidated statement of operations and comprehensive loss. 14. Risk management arising from financial instruments a) Credit risk Credit risk is the risk of loss associated with a counterparty’s inability to fulfill its payment obligations. The Company’s principal financial assets that expose it to credit risk are cash and trade receivables. The Company mitigates this risk by monitoring the credit worthiness of its customers and holding cash at financial institutions. The maximum credit exposure at May 31, 2025 is the carrying amount of cash and trade receivables. The Company’s exposure to credit risk is considered to be low, given the size and nature of the various counterparties involved and their history of performance. The Company has not historically incurred any significant credit loss in respect of its trade receivables. Based on consideration of all possible default events over the assets’ contractual lifetime, the expected credit loss in respect of the Company’s trade receivables was minimal as at May 31, 2025 and August 31, 2024. b) Interest rate risk Interest rate risk is the risk that the fair value or future cash flows of a financial instrument will fluctuate due to changes in market interest rates. The Company does not have any variable interest-bearing debt. c) Liquidity risk Liquidity risk is the risk that the Company will not be able to meet its financial obligations as they become due. The Company’s approach in managing liquidity is to ensure, to the extent possible, that it will have sufficient liquidity to meet its liabilities when due, by continuously monitoring actual and forecasted cash flows, refer to Going Concern in Note 1. d) Management of capital The Company’s objective of managing capital, comprising of shareholders’ equity, is to ensure its continued ability to operate as a going concern. The Company manages its capital structure and makes changes to it based on economic conditions. Management and the Board of Directors review the Company’s capital management approach on an ongoing basis and believe this approach, given the relative size of the Company, is reasonable. The Company is not subject to externally imposed capital requirements. The Company’s capital management objectives, policies and processes have remained unchanged during the period ended May 31, 2025. 19 Pineapple Financial Inc. Notes to the Condensed Interim Consolidated Financial Statements for period ended May 31, 2025 - Unaudited (Expressed in US Dollars) 15. Commitments and contingencies In the ordinary course of operating, the Company may from time to time be subject to various claims or possible claims. Management believes that there are no claims or possible claims that if resolved would either individually or collectively result in a material adverse impact on the Company’s financial position, results of operations, or cash flows. These matters are inherently uncertain, and management’s view of these matters may change in the future. See note 10 related to lease commitments. 16. Disaggregation of revenue Schedule of disaggregation of revenue May 31, 2025 May 31, 2024 Nine months ended May 31, 2025 May 31, 2024 $ $ Gross Billing 13,048,445 11,450,989 Commission expense 11,969,345 10,456,703 Commission revenue 1,079,099 994,286 Subscription revenue 559,993 560,261 Sponsorship revenue 169,928 - Other revenue 357,592 301,585 Underwriting revenue 92,784 115,245 Total revenue 2,259,396 1,971,377 May 31, 2025 May 31, 2024 Three months ended May 31, 2025 May 31, 2024 $ $ Gross Billing 4,400,201 4,128,220 Commission expense 4,158,334 3,717,457 Commission revenue 241,867 410,762 Subscription revenue 191,927 181,874 Sponsorship revenue 237,109 63,762 Other revenue 40,857 38,556 Underwriting revenue 35,143 41,494 Total revenue 746,903 736,448 17. Loan Company obtained $ 587,520 un-secured loan from directors. The loan is repayable in twelve months and carries 12 percent interest. $ 45,739 was interest payable as at May 31, 2025. Total loan outstanding is $ 633,259 . 18. Subsequent events The Company has evaluated subsequent events through the date of filing this Form 10-Q and has identified the following events requiring disclosure: 1. Reverse Stock Split — On June 26, 2025, following approval at a special meeting of shareholders, the Board of Directors approved a reverse stock split of the Company’s common shares at a ratio of 20-for-01 . The stock split was declared, but not yet effective as the date the financial statements are issued and therefore unaudited pro-forma retrospective adjusted earnings per share information is disclosed on the Statement of Operations and Comprehensive Loss in addition to the historical earnings per share disclosure. 2. NYSE American Delisting Notice — The Company received a notice of delisting from the NYSE American due to its shares trading below the minimum price requirement, resulting in classification as penny stock. The Company has filed an appeal, and the hearing is scheduled for July 17, 2025. Management expects that the reverse stock split will enable the Company’s securities to regain compliance and remain listed. 20 Item 2 Management’s Discussion and Analysis of Financial Condition and Results of Operations MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITIONS AND RESULTS OF OPERATIONS. Please read the following management’s discussion and analysis of our financial condition and results of operations, along with our condensed interim consolidated financial statements and the related notes and other information included in this Quarter Report on Form 10-Q. It is important to note that this discussion and analysis contain forward-looking statements with certain risks and uncertainties. These risks and uncertainties could cause our results to differ materially from anticipated in these forward-looking statements. You can find more information about these risks and uncertainties under the heading “Special Note Regarding Forward-Looking Statements” in Part I and elsewhere in this Form 10- Q. Special Note Regarding Forward-Looking Statements This Form 10-Q includes forward-looking statements that entail potential risks and uncertainties. These statements are usually identified by the use of specific terminology such as “anticipate,” “believe,” “could,” “estimate,” “expect,” “intend,” “may,” “plan,” “potential,” “predict,” “project,” “should,” “target,” “will,” “would” and other comparable terminology. All the statements in this Form 10-Q that are not about historical facts, including those related to our future operations, financial position, Revenue, projected costs, strategy, plans, management objectives, and expected market growth, are forward-looking. While reading this Form 10-Q, you should know that these statements do not guarantee our performance or results. They include known and unknown risks, uncertainties, and assumptions, as mentioned under the “Risk Factors” section in this Form 10-Q. We believe that these forward- looking statements are based on reasonable assumptions. Still, you must be aware that many factors, including those mentioned under the “Risk Factors” section in this Form 10-Q, could affect our financial results or operations and cause actual results to differ from those stated in the forward-looking statements. These statements were made as of the date of this Form 10-Q, and we are not obligated to update or revise any forward-looking statements made here to reflect any change in our expectations or any change in events, conditions, or circumstances on which these statements are based. All written or oral forward-looking statements made by us or on our behalf are qualified by the cautionary statements mentioned in this Form 10-Q. Objective In this section, we provide an analysis of the Company’s financial condition, cash flows, and results of operations from management’s perspective. We recommend you read this with the condensed interim consolidated financial statements and notes in Part II, Item 8 of this Annual Report on Form 10Q. Executive Summary We are a fintech company based in Ontario, Canada. Our tech-driven businesses focus on mortgages and insurance. Our goal is to provide clients with an industry-leading experience through our trusted digital solutions, which are simple and fast. Recent Developments Business Trends During 2022 and 2023, the Bank of Canada implemented multiple increases to the prime rate in response to heightened inflationary pressures, resulting in a significant rise in mortgage interest rates. In mid-2024, the Bank of Canada began easing monetary policy, reducing the policy rate by 1.75% in an effort to stabilize the economy and improve housing affordability. While this policy shift has helped improve consumer sentiment, elevated interest rates, coupled with renewed economic uncertainty, including emerging U.S. tariff threats, continue to weigh heavily on the Canadian economy. These external pressures have heightened market volatility, slowed cross-border investment activity, and increased caution among Canadian businesses and consumers. As a result, Pineapple Financial Inc. has continued to experience suppressed mortgage origination volumes, with overall real estate and lending activity remaining below pre-2022 levels. Although early signs of recovery are evident, future growth remains dependent on macroeconomic stability, interest rate trends, and the resolution of international trade uncertainties. Summary of the Nine months Ended May 31, 2025 Financial and Operational Highlights During the nine-month period ended May 31, 2025, we originated $1,183.62 million in residential mortgage loans, representing an increase of $99.85 million or 9.21% compared to the $1,083.77 million originated during the same period in the prior year. Our net loss for the period was $1.814 million, reflecting an improvement of $0.0.565 million, or 23.76%, compared to a net loss of $2.379 million in the nine months ended May 31, 2024. The improvement in net results is primarily attributable to higher loan origination volumes and ongoing cost management initiatives. The Company’s functional currency is the Canadian dollar (CAD), while its reporting currency is the U.S. dollar (USD). During the reporting period, the CAD depreciated by an average of 2.64% compared to the average CAD/USD exchange rate during the same period in the prior year, which had a modest impact on the translation of financial results. 21 Key Performance Indicators As part of our business operations, we closely track several key performance indicators (KPIs) that help us measure our performance. For example, we can evaluate our ability to generate revenue by monitoring our loan production KPIs and comparing our performance to that of the mortgage origination market. Additionally, we use KPIs related to our technology setup and underwriting processes to assess our performance further. Nine months period Ended May 31, 2025 2024 2023 Mortgage volume 1,183,621,251 1,083,771,257 966,531,247 Gross billing 13,048,445 11,450,989 11,097,689 Commission expense 11,969,345 10,456,703 10,340,720 Net sales revenue 1,079,099 994,286 756,969 Underwriting revenue 92,784 115,244 181,022 Subscription revenue 559,993 560,261 999,932 Other income 527,520 301,585 - Three months ended May 31, 2025 2024 2023 Mortgage volume 412,428,436 377,640,286 307,734,120 Gross billing 4,400,201 4.449,848 3,814,083 Commission expense 4,158,334 3,713,400 3,210,852 Net sales revenue 241,867 736,448 603,231 Underwriting revenue 35,143 41,454 16,751 Subscription revenue 191,927 181,701 106,572 Other income 277,966 - Gross Billing Revenue: Gross billing revenue refers to commissions collected from financial institutions with which the Company has contracts. The Company’s gross billing is based on a percentage of the mortgage amount funded between individuals referred by the Company and the financial institutions providing the mortgage. We serve as an agent in these transactions by offering a platform for other parties to deliver services to the end-user. For each contract with a customer, the Company identifies the contract, recognizes the performance obligations, determines the transaction price for each distinct performance obligation based on the relative stand-alone selling price of the goods or services to be delivered, and acknowledges revenue when each performance obligation is fulfilled in a manner that reflects the transfer of goods or services promised to the customer. The Company recognizes revenue when: there is a contract with a lender party and agent broker, the contract specifies the use of the platform service to finalize a mortgage deal, the mortgage deal is completed with the lending financial institution, and commissions are paid by the lending institution based on various criteria of the mortgage deal, including but not limited to interest rates available at that time, term, seasonality, collateral, income, purpose, and so forth. Revenue is measured at the fair value of the consideration received or receivable, representing amounts due for services provided in the normal course of business. Revenue is recognized at the end of the transaction upon the completion of all the actions listed above. A typical transaction incurs a commission fee payable to Pineapple Financial Inc. Subscription Revenue: Users can access and use our technology platform, MyPineapple, for a flat monthly service fee of $107. In exchange for this fee, MyPineapple users gain access to a network management system that enables them to perform back-office procedures more efficiently and effectively. This platform allows them to process the previously mentioned deal, prepare it, and complete the package for submission to the financial institution for funding. We have a robust user base that has experienced significant growth since our inception. Revenue is recognized at the beginning of the month when users are invoiced and pay the fee. Underwriting Fee: Users can optionally use our expert risk pre-assessment service, which assists them in pre-underwriting their loans before submission to a lender for approval and funding. This service significantly reduces the time for the lender partners’ assessment of the deal. For mortgages of $395,450 and greater, we charge an underwriting fee of $356; for mortgages lesser than $395,450, the Company charges an underwriting fee of $249. The Company has undertaken a special program to educate and inform users of this service in further detail. Approximately 40% of the deals originated by users are using this service. This program is intended to further increase the number of deals and improve the services offered. Other Income: Other income includes a technology setup fee and sponsorship fee. 22 Components of operating expenses Our operating expenses, as presented in the statement of operations data, include salaries, commissions and team member benefits, general and administrative expenses, marketing and advertising expenses, and others. Salaries and commissions and team member benefits All payroll expenses include our team members’ salaries, commissions, and benefits. Selling, general and administrative expenses Selling, general and administrative expenses include software subscriptions, license fees, professional services, marketing expenses, and other operating expenses. Share-based compensation Share-based compensation comprises equity awards and is measured and expensed accordingly under Accounting Standards Codification (“ASC”) 718 Compensation—Stock Compensation. Comparison of the nine months ended May 31, 2025 and May 31, 2024 Period Ended May 31, 2025 ($) May 31, 2024 ($) Increase/ (Decrease) ($) Increase/ (Decrease) % Gross Billing 14,228,741 13,422,366 806,375 15.23 Commission 11,969,345 11,450,989 518,356 15.92 Revenue 2,259,396 $ 1,971,377 288,019 11.78 Expenses Selling, general and administrative 1,522,778 1,545,900 (23,122 ) (3.56 ) Advertising and Marketing 617,987 648,197 (30,210 ) (19.08 ) Salaries, wages and benefits 1,223,722 1,825,786 (602,064 ) (30.14 ) Interest expense and bank charges 306,267 42,825 263,442 448..93 Depreciation 648,991 535,575 113,416 36.32 Government Incentive (70,657 ) (176,326 ) 105,669 (39.60 ) Total expense 4,249,088 $ 4,421,957 (172,869 ) (3.48 ) Loss from operations (1,989,692 ) (2,450,580 ) 460,888 (16.76 ) Foreign exchange gain (loss) (1,905 ) 10,751 (12,656 ) (62.67 ) Gain(loss) on change in fair value of warrant liability 341,765 42,251 299,514 180.05 Gain(loss) on change in fair value of conversion feature warrant liability - 18,134 (18,134 ) (100 ) Financing cost – warrant issuance (164,280 ) - (164,280 ) (100 ) Loss before income taxes (1,814,112 ) $ (2,379,444 ) (565,332 ) (23.76 ) Loss after income taxes (1,814,112 ) (2,379,444 ) Comparison of the three months years ended May 31, 2025 and May 31, 2024 Period Ended May 31, 2025 ($) May 31, 2024 ($) Increase/ (Decrease) ($) Increase/ (Decrease) % Gross Billing 4,905,237 4,449,848 455,389 10.23 Commission 4,158,334 3,713,400 444,934 11.98 Revenue 746,903 $ 736,448 10,455 1.42 Expenses Selling, general and administrative 527,835 491,666 36,169 7.36 Advertising and Marketing 292,489 265,395 27,094 10.21 Salaries, wages and benefits 394,648 593,202 (198,554 ) (33.47 ) Interest expense and bank charges 31,216 40,373 (9,157 ) (22.68 ) Depreciation 219,355 220,190 (835 ) (0.38 ) Government Incentive (22,109 ) (21,770 ) (43,879 ) (201.56 ) Total expense 1,443,434 $ 1,632,596 (189,162 ) (11.59 ) Loss from operations (696,531 ) (896,148 ) (199,617 ) (22.28 ) Foreign exchange gain (loss) (6,018 ) - (6,018 ) Gain(loss) on change in fair value of warrant liability 309,516 29,479 280,037 949.95 Gain(loss) on change in fair value of conversion feature liability - 18,064 (18,064 ) 100 Financing cots – warrants issued (164,703 ) - (164,703 ) 100 Loss before income taxes (557,736 ) $ (848,605 ) 290,869 (34.28 ) Loss after income taxes (557,736 ) (848,605 ) 23 Revenue and Cost Analysis For the nine-month period ended May 31, 2025, gross billings increased to $14.23 million, compared to $13.42 million for the same period last year, representing an increase of 15.23%. This reflects the Company’s continued resilience in its core mortgage and brokerage operations despite macroeconomic headwinds. While interest rate adjustments by the Bank of Canada have supported early signs of housing market recovery, transaction volumes remain below pre-pandemic levels. Commission expense, which primarily includes payments to mortgage agents, rose proportionately to $11.97 million, compared to $11.45 million in the same period last year, an increase of 15.92%. This increase is aligned with higher gross billings and demonstrates the Company’s strategy of leveraging experienced, high-volume agents to maintain transaction throughput. Revenue for the period increased to $2.26 million, up from $1.97 million for the prior-year period, reflecting an increase of 11.78%. This improvement is attributable to a continued focus on optimizing profitability by carefully managing agent mix and strategically reallocating resources toward more profitable channels. Margin Improvements and Operational Efficiency Total expenses for the nine months decreased by 3.48% year-over-year, driven primarily by a reduction in salaries, wages, and benefits, which declined by 30.14% compared to the prior period. This reduction reflects ongoing cost containment initiatives and efficiency measures. Increases in depreciation and interest expenses were partially offset by these savings. Other Items and Comprehensive Loss The Company recognized a gain of $341,765 related to the change in fair value of its warrant liability, up from $42,251 for the same period last year, due to issuance of warrants on May 07, 2025 and adjustments tied to market conditions. Financing costs related to warrant issuance totaled $164,280 for the period. As a result, the loss before income taxes improved to $(1.81) million, compared to $(2.38) million for the same period last year, reflecting disciplined cost controls and improved non-cash valuation items. Quarterly Performance For the three-month period ended May 31, 2025, gross billings increased to $4.91 million, compared to $4.45 million for the same quarter in the prior year, an increase of 10.23%. This steady performance highlights the Company’s ongoing ability to maintain transaction flow despite seasonal variations and a gradually stabilizing market. Commission expense rose by 11.98% to $4.16 million, in line with the increase in gross billings, as the Company continues to rely on high-volume agents to drive top-line growth. Revenue for the quarter increased slightly to $746,903 from $736,448 in the prior-year quarter, an increase of 1.42%. Total expenses for the quarter decreased by 11.59% to $1.44 million, primarily due to lower salary and benefit costs and continued operational efficiencies. The Company also recognized a gain of $309,516 on the change in the fair value of its warrant liability, compared to $29,479 in the same quarter last year, further supporting an improvement in net loss before taxes to $(557,736) from $(848,605) for the prior-year quarter, an improvement of 34.28%. Outlook Management remains focused on balancing transaction volume growth with disciplined cost management to protect margins and shareholder value. The Company will continue to monitor macroeconomic developments closely and is positioned to capture growth opportunities as the housing and mortgage markets stabilize, while maintaining operational efficiencies and strengthening its financial position. 24 Selling, General and Administrative Expenses. The breakdown of selling, general and administrative expenses are as follows: Nine months period ended Increase/ Increase/ Period Ended May 31, 2025 ($) May 31, 2024 ($) (Decrease) ($) (Decrease) % Software subscription 624,587 663,424 (38,837 ) (5.85 ) Office and general 114,864 117,213 (2,349 ) (2.00 ) Professional fee 108,359 157,531 (49,172 ) (31.21 ) Dues and subscription 364,287 146,964 217,323 147,.87 Rent 140,168 155,628 (15,460 ) (9.93 ) Consulting fee 45,483 45,167 316 0.70 Travel 25,467 137,940 (112,473 ) (81.54 ) Donations 789 7,406 (6,617 ) (89.35 ) Lease expense 507 54,946 (54,439 ) (99.08 ) Insurance 98,267 59,681 38,586 64.65 1,522,778 1,545,900 (23,122 ) (1.50 ) Selling, General, and Administrative Expenses For the nine-month period ended May 31, 2025, selling, general, and administrative (SG&A) expenses totaled $1,522,778, representing a slight decrease of 1.50% compared to $1,545,900 for the same period in the prior year. This reflects the Company’s continued commitment to disciplined cost management while strategically reallocating spending to priority areas. Software Subscription Software subscription expenses decreased by $38,837 (5.85%), from $663,424 to $624,587. The reduction is primarily due to the discontinuation of Salesforce subscriptions effective April 1, 2025, following the successful implementation of the Company’s internally developed system, which is expected to improve cost efficiency and data control. Office and General Office and general expenses decreased modestly by $2,349 (2.00%) year-over-year, reflecting tight cost discipline across day-to-day administrative expenditures. Professional Fees Professional fees decreased by $49,172 (31.21%), from $157,531 to $108,359. This reduction is due to decreased reliance on external legal and advisory services after the Company streamlined its compliance and reporting workflows following its public listing. Dues and Subscriptions Dues and subscriptions increased significantly by $217,323 (147.87%) to $364,287 from $146,964 in the prior period. This increase is attributable to the Company’s expanded engagement with industry groups, data services, and technology associations to strengthen market insights and maintain competitive positioning in a dynamic regulatory environment. Rent Rent expense decreased by $15,460 (9.93%) to $140,168 from $155,628, reflecting the renegotiation of lease terms and more efficient space utilization aligned with hybrid work arrangements. Consulting Fees Consulting fees remained broadly flat at $45,483, compared to $45,167 in the same period last year, reflecting consistent use of specialized external expertise for targeted strategic initiatives. Travel Travel expenses decreased significantly by $112,473 (81.54%), from $137,940 to $25,467. The decrease reflects continued restrictions on discretionary travel and the increased use of virtual collaboration tools across operations and stakeholder engagement. Donations Donations decreased by $6,617 (89.35%), from $7,406 to $789, in line with management’s decision to prioritize cost containment and focus resources on core business operations. Lease Expense Lease expense decreased materially by $54,439 (99.08%) to $507 from $54,946, primarily due to the termination of non-core leased assets and a shift toward more cost-effective operating arrangements. Insurance Insurance expenses increased by $38,586 (64.65%) to $98,267, compared to $59,681 in the prior year. The increase primarily reflects higher costs for enhanced coverage under the Company’s director and officer (D&O) insurance program and expanded liability protection requirements as a public company. 25 The breakdown of selling, general and administrative expenses are as follows: Three months period ended Increase/ Increase/ Period Ended May 31, 2025 ($) May 31, 2024 ($) (Decrease) ($) (Decrease) % Software subscription 174,116 260,951 (86,835 ) (33.28 ) Office and general 32,112 60,558 (28,446 ) (46.97 ) Professional fee 47,866 11,871 35,995 303.21 Dues and subscription 165,688 (5,149 ) 170,837 3,317.88 Rent 54,997 57,528 (2,531 ) (4.40 ) Consulting fee 15,888 20,663 (4,775 ) (23.11 ) Travel 2,108 51,867 (49,759 ) (95.94 ) Donations - 2,759 (2,759 ) (100.00 ) Lease expense (942 ) 956 (1,898 ) (198.55 ) Insurance 36,002 29,661 6,341 21.38 527,835 491,666 36,169 7.36 Selling, General, and Administrative Expenses For the three-month period ended May 31, 2025, selling, general, and administrative (SG&A) expenses totaled $527,835, representing an increase of 7.36% compared to $491,666 for the same period in the prior year. The increase reflects higher professional services and subscription costs to support operational requirements during the quarter. Software Subscription Software subscription expenses decreased by $86,835 (33.28%) to $174,116, compared to $260,951 for the same quarter last year. This decrease is primarily due to the Company’s decision to discontinue its Salesforce subscription effective April 1, 2025, following the launch of its internally developed system. Office and General Office and general expenses decreased by $28,446 (46.97%) to $32,112, reflecting tighter cost controls and reduced spending on day-to-day administrative costs during the quarter. Professional Fees Professional fees increased significantly by $35,995 (303.21%) to $47,866, compared to $11,871 in the same quarter last year. The increase is due to higher legal, audit, and advisory fees related to regulatory filings and corporate compliance activities during the quarter. Dues and Subscriptions Dues and subscriptions increased by $170,837, moving from a net credit of $(5,149) in the prior period to $165,688 in the current quarter. The increase reflects expanded participation in industry groups and access to specialized data platforms to enhance market positioning. Rent Rent expenses remained relatively stable, decreasing slightly by $2,531 (4.40%) to $54,997, reflecting continued optimization of office space. Consulting Fees Consulting fees decreased by $4,775 (23.11%) to $15,888, reflecting lower reliance on external consultants during the quarter as core projects were transitioned to in-house teams. Travel Travel expenses decreased by $49,759 (95.94%) to $2,108, compared to $51,867 in the prior-year quarter. The decrease is due to continued travel restrictions and increased use of virtual meetings for internal and external engagement. Donations No donations were made during the quarter, compared to $2,759 in the same period last year, consistent with the Company’s focus on directing funds toward operational priorities. Lease Expense Lease expense decreased by $1,898 (198.55%), reflecting adjustments for the reduction of non-core leased equipment. Insurance Insurance expenses increased by $6,341 (21.38%) to $36,002, reflecting ongoing adjustments for expanded coverage under the Company’s director and officer insurance program and general liability coverage. 26 Expenses Nine months period ended Increase/ Increase/ Period Ended May 31, 2025 ($) May 31, 2024 ($) (Decrease) ($) (Decrease) % Advertising and marketing 617,987 648,197 (30,210 ) (4.66 ) Salaries, wages and benefits 1,223,722 1,825,786 (602,064 ) (32.98 ) Interest expense and bank charges 306,267 42,825 263,442 614.16 Depreciation 648,991 535,575 113,416 21.18 Government incentive (70,657 ) (176,326 ) (105,669 ) (59.93 ) Operating Expenses and Other Income For the nine-month period ended May 31, 2025, the Company continued to focus on disciplined cost control while investing in areas that support operational efficiency and regulatory compliance. Below is a breakdown of key expense line items: Advertising and Marketing Advertising and marketing expenses decreased by $30,210 (4.66%) to $617,987, compared to $648,197 in the same period last year. The decrease reflects more targeted marketing campaigns and improved allocation of digital marketing spend to higher-conversion channels. Salaries, Wages and Benefits Salaries, wages and benefits decreased by $602,064 (32.98%) to $1,223,722, compared to $1,825,786 in the prior year. The decrease is primarily due to workforce optimization initiatives, including streamlining certain non-core roles and aligning staffing levels with current transaction volumes. Interest Expense and Bank Charges Interest expense and bank charges increased significantly by $263,442 (614.16%) to $306,267, compared to $42,825 for the same period last year. The increase is primarily driven by higher interest costs related to new financing facilities secured to support working capital needs and costs associated with the issuance of warrants during the period. Depreciation Depreciation expense increased by $113,416 (21.18%) to $648,991, compared to $535,575 in the prior period. The increase reflects additional amortization of new capitalized technology investments, including the internally developed platform that replaced the Salesforce system. Government Incentive Government incentives decreased by $105,669 (59.93%) to $(70,657), compared to $(176,326) in the prior year. The reduction reflects lower available grant funding in the current fiscal period as prior-year government support programs concluded. Liquidity and Capital Resources Our primary liquidity needs include working capital and capital expenditures, particularly those related to technological enhancements, investments in skilled personnel, and marketing services. These three categories have represented a significant share of our liquidity and capital resource demands throughout the year. We primarily rely on cash on hand and cash flows generated from our operations to satisfy these needs. The following table summarizes our cash flows from operating, investing and financing activities: Nine months period ended Increase/ Year Ended May 31, 2025 ($) May 31, 2024 ($) (Decrease) ($) Cash (used) provided in operating activities (439,198 ) (1,443,610 ) (1,004,412 ) Cash (used) provided by financing activities 1,836,327 2,480,806 (644,479 ) Cash (used) provided in investing activities (811,443 ) (901,185 ) (89,742 ) Cash at the end of the period 1,134,583 748,769 385,814 27 Net cash flow from (used in) operating activities Nine months period ended Description May 31, 2025 ($) May 31, 2024 ($) Operating activities Net loss (1,814,112 ) (2,379,444 ) Adjustments for the following non-cash items: Depreciation of property and equipment 64,201 65,300 Amortization of intangible assets 430,391 369,993 Depreciation on right of use asset 154,399 100,282 Interest expense on lease liability 39,601 47,482 Change in fair value of warrant liability 341,765 (42,251 ) Foreign exchange gain (loss) (1,905 ) (10,751 ) Change in fair value of warrant liability Change in fair value of conversion feature liability (18,133 ) Net changes in non-cash working capital balances: Trade and other receivables (25,238 ) 607,724 Prepaid expenses and deposits 76,090 65,976 Accounts payable and accrued liabilities 337,367 (74,756 ) Deferred government incentive 81,164 (175,032 ) Deferred revenue 39,407 - For the nine-month period ended May 31, 2025, net cash used in operating activities was $(439,198), a substantial improvement compared to $(1,443,610) for the same period in the prior year. The reduction in operating cash outflows reflects improved operational efficiencies, continued cost discipline, and a more effective approach to managing working capital. The net loss for the period was $(1,814,112), compared to $(2,379,444) for the same nine-month period last year. This improvement is primarily due to more efficient operations, tighter expense management, and adjustments related to non-cash fair value changes. Key non-cash adjustments included: ● Amortization of intangible assets totaling $430,391, up from $369,993, reflecting continued investment in proprietary technology and systems. ● Depreciation of property and equipment was $64,201, in line with $65,300 last year, while depreciation on right-of-use assets increased to $154,399, compared to $100,282, due to new office and equipment lease commitments. ● Interest expense on lease liability totaled $39,601, slightly lower than $47,482 in the prior period. ● The Company recorded a gain on change in fair value of warrant liability of $341,765, compared to a loss of $(42,251) last year, due to updated valuations reflecting prevailing capital market conditions. ● A foreign exchange loss of $(1,905) was recorded, compared to a gain of $10,751 in the prior-year period. Net changes in non-cash working capital provided further support for improved operating cash flow: ● Trade and other receivables increased slightly by $(25,238), reflecting timing differences on collections. ● Prepaid expenses and deposits increased by $76,090, up from $65,976, due to upfront payments for strategic services and subscriptions. ● Accounts payable and accrued liabilities increased by $337,367, compared to a reduction of $(74,756) last year, highlighting more effective management of vendor payments. ● Deferred government incentives rose by $81,164, compared to a decrease of $(175,032) in the prior year. ● Deferred revenue of $39,407 reflects upfront billings for services to be delivered in future periods. Net cash provided by financing activities for the nine-month period amounted to $1,836,327, compared to $2,480,806 in the same period last year. The decrease of $644,479 is primarily attributable to lower net proceeds from financing transactions during the period, while the Company continued to utilize equity and debt facilities to support operations and growth initiatives. Net cash used in investing activities was $(811,443), compared to $(901,185) in the prior period, a decrease of $89,742. This reflects disciplined investment in intangible assets and capital expenditures as the Company focuses on enhancing its proprietary systems and technology infrastructure. 28 As of May 31, 2025, the Company’s cash and cash equivalents stood at $1,134,583, an increase of $385,814 compared to $748,769 at the end of the same period last year, demonstrating progress in strengthening liquidity despite ongoing investments in technology and working capital. Management remains focused on maintaining a healthy cash position to meet near-term operating requirements while supporting strategic investments. The Company continues to evaluate both non-dilutive and equity-based funding options to strengthen its balance sheet, expand its technology roadmap, and drive long-term shareholder value. The following table presents our liquidity: As at: May 31, 2025 ($) August 31, 2024 ($) Cash 1,134,583 580,356 Trade and other receivables 180,462 155,224 Prepaid expenses and deposit 81,821 157,911 1,396,866 893,491 As of May 31, 2025, Pineapple Financial maintained a solid liquidity position with $1,134,583 in cash, supplemented by $180,462 in trade and other receivables and $81,821 in prepaid expenses and deposits, bringing total current liquid assets to $1,396,866. This compares favorably to $893,491 as at August 31, 2024, reflecting an increase of $503,375. The improvement is primarily attributable to new equity injection, stronger revenue generation, continued expense discipline, and the Company’s successful execution of targeted financing activities during the period. Management remains focused on preserving adequate liquidity to meet short-term obligations while supporting strategic investments to drive sustainable growth. The Company continues to monitor its cash flows and working capital needs to ensure prudent resource allocation in line with its operational and expansion objectives. Critical Accounting Policies and Significant Judgments and Estimates This management’s discussion and analysis of the financial condition and results of operations is based on our financial statements, which have been prepared in accordance with U.S. GAAP. The preparation of these financial statements requires us to make estimates and assumptions that affect the reported amounts of assets and liabilities, disclosure of contingent assets and liabilities at the date of the financial statements, and the reported amounts of Revenue and expenses during the reported period. Per U.S. GAAP, we base our estimates on historical experience and various other assumptions we believe to be reasonable under the circumstances. Actual results may differ from these estimates if conditions differ from our assumptions. While our significant accounting policies are more fully described in Note 2 in the “Notes to Financial Statements,” we believe the following accounting policies are critical to making effective judgments and estimates in preparing our financial statements. Revenue Recognition The Company has adopted ASC 606, Revenue from Contracts with Customers, which provides a single comprehensive model for revenue recognition. The core principle of the standard is that Revenue should be recognized when goods or services are transferred to customers at an amount that reflects the consideration to which the entity expects to be entitled in exchange for those goods or services. The standard introduced a new contract- based revenue recognition model with a measurement approach that is based on an allocation of the transaction price. It establishes a five-step model to account for Revenue arising from contracts with customers. Under this standard, Revenue is recognized at an amount that reflects the consideration to which an entity expects to be entitled in exchange for transferring goods or services to a customer. The standard requires entities to exercise judgement, taking into consideration all of the relevant facts and circumstances when applying each step of the model to contracts with customers. Additionally, the standard specifies the accounting for incremental costs of obtaining a contract and the costs directly related to fulfilling a contract. 29 When the Company transfers goods or services to a customer, Revenue is recognized at an amount that reflects the consideration expected to be received. The Company operates an online platform powered by Salesforce, that enables brokers and agents to efficiently close deals. The Company’s subsidiary, Pineapple Insurance Inc., generates Revenue by charging premiums for insurance policies and services. Pineapple Insurance is affiliated with a major insurance company, from which it earns commissions for providing services, primarily mortgage insurance. Mortgage insurance is a requirement for each mortgage. Pineapple Insurance acts as the agent that supplies insurance services to the consumer and is paid a commission from the premiums collected by the insurance company whose products and services it provides to the end consumer. Additionally, Pineapple Insurance has adopted ASC 606. Basis of presentation, functional and presentation currency The Company’s headquarters is in Ontario, Canada, and the functional currency is in Canadian Dollars (CAD) with the presentation currency being US Dollars (USD). The Company’s subsidiaries have a functional currency of CAD and presentation currency of USD which have been applied consistently. There will be a foreign currency translation undertaken to report under US GAAP which will be the basis of presentation. Lease Accounting The relevant criteria applicable is ASC 842. We assess at contract inception whether a contract is, or contains, a lease. That is, if the contract conveys the right to control the use of an identified asset for a period of time in exchange for consideration. We apply a single recognition and measurement approach for all leases, except for short-term leases and leases of low-value assets. We recognize lease liabilities to make lease payments and right-of- use assets representing the right to use the underlying assets. At the commencement date of the lease, we recognize lease liabilities measured at the present value of lease payments to be made over the lease term. Lease payments include fixed payments (including in-substance fixed payments) less any lease incentives receivable, variable lease payments that depend on an index or a rate, and amounts expected to be paid under residual value guarantees. Lease payments also include the exercise price of a purchase option reasonably certain to be exercised by us and payments of penalties for terminating the lease, if the lease term reflects us exercising the option to terminate. Variable lease payments that do not depend on an index or a rate are recognized as expenses in the period in which the event or condition that triggers the payment occurs. In calculating the present value of lease payments, we use our incremental borrowing rate at the lease commencement date because the interest rate implicit in the lease is not readily determinable. After the commencement date, the amount of lease liabilities is increased to reflect the accretion of interest and reduced for the lease payments made. In addition, the carrying amount of lease liabilities is remeasured if there is a modification, a change in the lease term, a change in the lease payments (e.g., changes to future payments resulting from a change in an index or rate used to determine such lease payments) or a change in the assessment of an option to purchase the underlying asset. We recognize right-of-use assets at the commencement date of the lease (i.e., the date the underlying asset is available for use). Right-of-use assets are measured at cost, less any accumulated depreciation and impairment losses, and adjusted for any remeasurement of lease liabilities. The cost of right-of-use assets includes the amount of lease liabilities recognized, initial direct costs incurred, and lease payments made at or before the commencement date less any lease incentives received. Right-of-use assets are depreciated on a straight-line basis over the shorter of the lease term and the estimated useful lives of the assets. 30 Investments We invested in MCommercial, a commercial mortgage firm based in Montreal and Toronto, Canada, representing 5% of the total issued and outstanding shares. This strategic partnership allows Pineapple residential mortgage agents to access a leading commercial mortgage firm and experts, which will expand their product offerings, service levels, and corporate Revenue through increased transactions. The Company entered into a share purchase agreement with 9142-2964 Quebec Inc., pursuant to which it acquired five Class A Shares of 7326904 Canada Inc. (doing business as Mortgage Alliance Corporation) (“Alliance”), representing 5% of the total issued and outstanding shares of Alliance. Alliance is a mortgage brokerage firm based in Ontario, Canada, with locations in Calgary, Vancouver, and Halifax. The total value of both investments was recorded at fair value, and any impairment loss is recognized in the profit and loss account. Share Based Compensation Stock-based compensation is accounted for based on the requirements of the Share-Based Payment Topic of ASC 718, “Compensation — Stock Compensation” (“ASC 718”), which requires recognition in the financial statements of the cost of employee, non-employee and director services received in exchange for an award of equity instruments over the period the employee, non-employee or director is required to perform the services in exchange for the award (presumptively, the vesting period). ASC 718 also requires measurement of the cost of employee, non- employee, and director services received in exchange for an award based on the grant-date fair value of the award. The Company has a share option plan (the “Plan”) to attract, retain and motivate qualified directors, officers, employees, and consultants whose present and future contributions are important to the success of the Company by offering them an opportunity to participate in the Company’s future performance through the award of share options. Each share option converts into one common share of Pineapple Financial Inc. on exercise. No amounts are paid or payable by the recipient on receipt of the option. The options carry neither right to dividends nor voting rights. Options may be exercised at any time from the date of vesting to the date of their expiry. In 2017, the Plan was amended such that the total number of common shares reserved and available for grant and issuance pursuant to the Plan is to equal 10% of the issued and outstanding common shares of the Company. Options granted on June 14, 2021, vest over a 2-year period whereby 25% of the options granted vested on the date of grant, and the remaining unvested options vest in equal instalments every 6-months thereafter. The fair value of stock options granted was $1,317,155. These options were fully vested in year ended August 31, 2023. On July 6, 2023, we completed a 1-for-3.9 reverse stock split, or the Reverse Split, effective immediately. Consequently, all the share numbers, shares prices, and exercise prices have been retroactively adjusted in these condensed interim consolidated financial statements for all periods presented. Controls and Procedures While the Company is not currently required to maintain an effective internal controls system, we recognize the importance of strong internal controls and have proactively initiated steps to establish and enhance our control environment. These measures include: ● Employing skilled staff in financial, accounting, and external reporting roles, focusing on segregation of duties. 31 ● Conducting regular reconciliations to ensure accurate recording, correct classification, and balanced books. ● Ensuring timely and accurate recording of expenses, liabilities, and other accounting entries in accordance with the matching principle. ● Maintaining a detailed fixed assets register to track users, departments, and assets. ● Requiring internal review and approval of accounting transactions by at least two independent personnel. ● Documenting processes, assumptions, and conclusions related to significant estimates. ● Establishing comprehensive documentation of accounting policies and procedures. As of May 31, 2025, under the supervision and with the participation of management, including our principal executive officer and principal financial officer, we conducted an evaluation of the effectiveness of our internal control over financial reporting. Based on this assessment, management concluded that our disclosure controls and procedures were effective as of May 31, 2025. Improvements made during the year include carrying out independent reviews, establishing approval processes for transactions and reconciliations, and hiring additional personnel to enhance our control environment. Plans are in place to further improve controls by segregating duties and refining processes, thus ensuring robust and effective internal controls that uphold the integrity of our financial reporting. Financial Instruments As of May 31, 2025, the Company’s financial instruments include cash, trade and other receivables, investments, accounts payable, and accrued liabilities. As per ASC 820, Fair value measurement establishes a fair value hierarchy based on the level of independence, objective evidence surrounding the inputs used to measure fair value. A financial instrument’s categorising within the fair value hierarchy is based upon the lowest level of input that is significant to the fair value measurement. i) Level 1 fair value measurements are those derived from quoted prices (unadjusted) in active markets for identical assets or liabilities; ii) Level 2 fair value measurements are those derived from inputs other than quoted prices included within Level 1 that are observable for the asset or liability, either directly (i.e., as prices) or indirectly (i.e., derived from prices); and iii) Level 3 fair value measurements are those derived from valuation techniques that include inputs for the asset or liability that are not based on observable market data (unobservable inputs). The following table provides the fair values of the financial assets in the Company’s consolidated statements of financial position, categorized by hierarchical levels and their related classifications. 32 As of May 31, 2025 Level 1 Level 2 Level 3 Total Assets: Cash 1,134,583 1,134,583 Investment 9,847 9,847 Risks and Uncertainties The Company’s business is subject to numerous risks and uncertainties, including those described elsewhere in this MD&A, as well as general economic and market risks. These risk factors could materially affect the Company’s future operating results and could cause actual events to differ materially from those described in forward-looking information relating to the Company. As part of our regular business operations, we face various risks that can impact our profitability and operations. These risks can be broadly categorized as interest rate risk, credit risk, counterparty risk, and risks associated with the pandemics like COVID-19. Interest rate risk We do not face interest rate risk as we do not have any variable-rate loans or borrowings. Credit risk Credit risk is the risk of financial loss to the Corporation if a counterparty to a financial instrument fails to meet its contractual obligations. The Corporation’s credit risk is mainly attributable to its cash and trade and other receivables. The Corporation has determined that its exposure to credit risk on its cash is minimal as the Corporation’s cash are held with financial institutions in Canada. Our primary source of credit risk relates to the possibility of Core Business Operation’s brokerages or other customers not paying receivables. Core Business Operations manages its credit risk by performing credit risk evaluations on its brokerages and agents and monitoring overdue trade and other receivables. As of May 31, 2025, $83,967 of our trade receivables are greater than 90 days outstanding, as compared to $57,165 for May 31, 2024. A decline in economic conditions or other adverse conditions experienced by brokerage and agents could impact the collectability of the Corporation’s accounts receivable. Our maximum exposure to credit risk approximates the carrying value of the assets on the Corporation’s consolidated statements of financial position. As at: May 31, 2025 ($) August 31, 2024 ($) Cash 1,134,583 580,356 Trade and other receivables 180,462 155,224 Prepaid expenses and deposit 81,821 157,911 1,396,866 893,491 33 Item 3. Quantitative and Qualitative Disclosures about Market Risk As a smaller reporting company, this disclosure is not required. Item 4. Controls and Procedures Evaluation of Disclosure Controls and Procedures We are transitioning to and will maintain disclosure controls and procedures that are designed to ensure that information required to be disclosed by us in reports that we file or submit under the Exchange Act is recorded, processed, summarized and timely reported as provided in SEC rules and forms and that such information is accumulated and communicated to our management, as appropriate, to allow for timely decisions regarding required disclosure. We will periodically review the design and effectiveness of our disclosure controls and procedures, including compliance with various laws and regulations that apply to our operations. We will make modifications to improve the design and effectiveness of our disclosure controls and procedures and may take other corrective action if our reviews identify a need for such modifications or actions. In designing and evaluating the disclosure controls and procedures, we recognize that any controls and procedures, no matter how well designed and operated, can provide only reasonable assurance of achieving the desired control objectives, and we will apply judgment in evaluating the cost-benefit relationship of possible controls and procedures. In addition, the design of any system of controls also is based in part upon certain assumptions about the likelihood of future events, and there can be no assurance that any design will succeed in achieving its stated goals under all potential future conditions; over time, controls may become inadequate because of changes in conditions, or the degree of compliance with policies or procedures may deteriorate. Because of the inherent limitations in a control system, misstatements due to error or fraud may occur and not be detected. Changes in Internal Control Over Financial Reporting There have been no changes in our internal control over financial reporting that occurred during our last fiscal quarter that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting. PART II. OTHER INFORMATION Item 1 Legal Proceedings. To our best knowledge, we are currently not a party to any legal proceedings that, individually or in the aggregate, are deemed to be material to our financial condition or results of operations. Item 1A Risk Factors. Our securities are currently quoted on the OTC Pink Open Market, which may adversely affect the liquidity and market price of our common shares. Following a notice of delisting from the NYSE American due to non-compliance with certain continued listing standards, our common shares commenced trading on the OTC Pink Open Market (OTCPK). While we have appealed the delisting decision and the process remains pending, there is no assurance that the appeal will be successful or that we will be able to regain listing on a national securities exchange. Trading on the OTC Pink Open Market is generally less liquid and more volatile than trading on a national exchange. Investors may find it more difficult to buy or sell our common shares, and the market price may be subject to greater fluctuations with limited trading volume. Additionally, trading on the OTC Markets may limit our ability to access capital markets, attract institutional investors, or maintain analyst coverage. Should we be unable to regain listing on a national exchange, our business, financial condition, and shareholder value could be materially adversely affected. The Reverse Stock Split may not achieve the intended results and could adversely affect the liquidity of our common shares. On June 26, 2025, the Company’s shareholders approved, and the Board of Directors authorized, a reverse stock split of the Company’s common shares at a ratio of 1-for-20. While the reverse stock split is intended to increase the trading price of our common shares and assist in regaining compliance with the continued listing requirements of the NYSE American, there can be no assurance that the reverse stock split will have the desired effect. The trading price of our common shares may decline below the required levels despite the reverse split, or the market may perceive the reverse split negatively, resulting in reduced liquidity or increased volatility. In addition, the reverse split could adversely impact the perception of our Company among investors, analysts, and other market participants Item 2 Unregistered Sales of Equity Securities and Use of Proceeds. There were no issuances of unregistered sales of equity securities during the nine months ended May 31, 2025. 34 Item 3 Defaults Upon Senior Securities. None. Item 4 Mine Safety Disclosures. Not applicable. Item 5 Other Information. On June 26, 2025, the Company’s shareholders approved, and the Board of Directors subsequently authorized, a reverse stock split of the Company’s common shares at a ratio of 1-for-20. The reverse stock split was implemented as part of the Company’s strategy to regain compliance with the continued listing standards of the NYSE American, specifically relating to minimum share price requirements. The Company is working with its transfer agent, regulatory authorities, and market participants to complete all necessary steps for the effective execution of the reverse stock split, including notification filings with FINRA and applicable Canadian securities regulators. The Company remains committed to maintaining its public listing and enhancing shareholder value. Item 6. EXHIBITS Exhibit No. Description 31.1 * Certification of Chief Executive Officer pursuant to Rule 13a-14(a)/15d-14(a). 31.2 * Certification of Chief Financial Officer pursuant to Rule 13a-14(a)/15d-14(a). 32.1 * Certification of Chief Executive Officer pursuant to Section 906 of the Sarbanes-Oxley Act of 2002. 32.2 * Certification of Chief Financial Officer pursuant to Section 906 of the Sarbanes-Oxley Act of 2002. 101.INS * Inline XBRL Instance Document. 101.SCH* * Inline XBRL Taxonomy Extension Schema Document. 101.CAL* * Inline XBRL Taxonomy Extension Calculation Linkbase Document. 101.DEF* * Inline XBRL Taxonomy Extension Definition Linkbase Document. 101.LAB* * Inline XBRL Taxonomy Extension Label Linkbase Document. 101.PRE * Inline XBRL Taxonomy Extension Presentation Linkbase Document. 104 The cover page from the Company’s Quarterly Report on Form 10-Q for the quarter ended May 31, 2025, formatted in Inline XBRL (included in Exhibit 101). * Filed herewith. 35 SIGNATURES Pursuant to the requirements of Section 13 or 15(d) of the Securities Exchange Act of 1934, the Registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized. PINEAPPLE FINANCIAL INC. Date: July 14, 2025 By: /s/ Shubha Dasgupta Shubha Dasgupta Chief Executive Officer Date: July 14, 2025 By: /s/ Sarfraz Habib Sarfraz Habib Chief Financial Officer 36