PAPL / Pineapple Financial Inc. - SEC Filings, Annual Report, Proxy Statement

Pineapple Financial Announces the Launch of $100M Injective Digital Asset Treasury Strategy, Becoming the First Publicly Traded INJ Holder Worldwide

Exhibit 99.1 Pineapple Financial Announces the Launch of $100M Injective Digital Asset Treasury Strategy, Becoming the First Publicly Traded INJ Holder Worldwide INJ, the native asset of Injective, the leading finance-focused blockchain, provides one of the higher staking yields in the industry while creating potential new liquidity rails for the estimated multi-trillion dollar tokenization market

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 2, 2025 PINEAPPLE FINAN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 2, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 25, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable 00-0000000 (State or other jurisdiction (Commission (IRS Empl

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 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

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 26, 2025 PINEAPPLE FINANCIAL

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 26, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable 00-0000000 (State or other jurisdiction (Commission (IRS Empl

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy State

Pineapple Financial Inc. Responds to NYSE

Exhibit 99.1 Pineapple Financial Inc. Responds to NYSE Commencement of Proceedings to Delist May 19, 2025 4:00 PM EDT | Source: Pineapple Financial Inc. Toronto, Ontario-(Newsfile Corp. - May 19, 2025) - Pineapple Financial (OTC Pink: PAPLF) announced today that it is working on certain curative actions to regain compliance to maintain its listing and appeal the NYSE’s determination to delist its

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 14, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable 00-0000000 (State or other jurisdiction (Commission (IRS Emplo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

Form of Common Warrant.

Exhibit 4.1 WARRANT TO PURCHASE COMMON SHARES PINEAPPLE FINANCIAL INC. Warrant Shares: Initial Exercise Date: , 2025 Issue Date: , 2025 THIS WARRANT TO PURCHASE COMMON SHARES (the “Warrant”) certifies that, for value received, or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on or after the da

Pineapple Financial Inc. (PAPL) Announces Pricing of $1.5 Million Public Offering

Exhibit 99.1 Pineapple Financial Inc. (PAPL) Announces Pricing of $1.5 Million Public Offering Toronto, Ontario-(Newsfile Corp. - May 2, 2025) - Pineapple Financial Inc. (NYSE American: PAPL) (“Pineapple” or the “Company”), a leading Canadian mortgage technology and brokerage firm, today announced the pricing of a public offering of 10,000,000 units, each unit consisting of either one share of the

Pineapple Financial Inc. (PAPL) Announces Closing of $1.5 Million Public Offering

Exhibit 99.2 Pineapple Financial Inc. (PAPL) Announces Closing of $1.5 Million Public Offering Toronto, Ontario-(Newsfile Corp. - May 5, 2025) - Pineapple Financial Inc. (NYSE American: PAPL) (“Pineapple” or the “Company”), a leading Canadian mortgage technology and brokerage firm, today announced the closing of its public offering (the “Offering”) with aggregate gross proceeds to the Company of $

Entry into a Material Definitive Agreement, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 1, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable 00-0000000 (State or other jurisdiction (Commission (IRS Employ

Placement Agency Agreement, dated May 1, 2025, by and between Pineapple Financial Inc. and D. Boral Capital LLC.

Exhibit 1.1 Exhibit [▲] PLACEMENT AGENCY AGREEMENT [▲], 2025 Pineapple Financial Inc. Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1 Attn: Shubha Dasgupta, Chief Executive Officer Dear Mr. Dasgupta: This letter (the “Agreement”) constitutes the agreement between D. Boral Capital LLC (the “Placement Agent”) and Pineapple Financial Inc., a company organized under the law of Canada (the

10,000,000 Units, with each Unit consisting of One Common Share and One Warrant to Purchase One Common Share 10,000,000 Common Shares Underlying the Warrants PINEAPPLE FINANCIAL INC.

Filed Pursuant to Rule 424(b)(4) Registration No. 333-286783 PROSPECTUS 10,000,000 Units, with each Unit consisting of One Common Share and One Warrant to Purchase One Common Share 10,000,000 Common Shares Underlying the Warrants PINEAPPLE FINANCIAL INC. Pineapple Financial Inc. is offering on a best efforts basis, 10,000,000 units (the “Units”), at a public offering price of $0.15 per Unit. Each

Form of Pre-Funded Warrant

Exhibit 4.2 PRE-FUNDED COMMON SHARES PURCHASE WARRANT PINEAPPLE FINANCIAL INC. Warrant Shares: [] Initial Exercise Date: [●], 2025 THIS PRE-FUNDED COMMON SHARES PURCHASE WARRANT (the “Warrant”) certifies that, for value received, or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on or after the

Form of Securities Purchase Agreement

Exhibit 10.9 SECURITIES PURCHASE AGREEMENT THIS SECURITIES PURCHASE AGREEMENT (this “Agreement”) is entered into and made effective as of [ ] [ ], 2025, between Pineapple Financial Inc., a company organized under the laws of Canada (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers

Form of Placement Agent Agreement

Exhibit 1.1 Exhibit [▲] PLACEMENT AGENCY AGREEMENT [▲], 2025 Pineapple Financial Inc. Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1 Attn: Shubha Dasgupta, Chief Executive Officer Dear Mr. Dasgupta: This letter (the “Agreement”) constitutes the agreement between D. Boral Capital LLC (the “Placement Agent”) and Pineapple Financial Inc., a company organized under the law of Canada (the

PINEAPPLE FINANCIAL INC. Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1

PINEAPPLE FINANCIAL INC. Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1 May 1, 2025 Securities and Exchange Commission Division of Corporation Finance 100 F Street N.E. Washington, D.C. 20549 Attention: Aisha Adegbuyi Re: Pineapple Financial Inc. Registration Statement on Form S-1 Submitted April 25, 2025 Ladies and Gentlemen: Pursuant to Rule 461 promulgated under the Securities Act

D. Boral Capital LLC 590 Madison Avenue, 39th Floor New York, NY 10022

D. Boral Capital LLC 590 Madison Avenue, 39th Floor New York, NY 10022 May 1, 2025 VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, DC 20549 Attention: Aisha Adegbuyi Re: Pineapple Financial Inc. Registration Statement on Form S-1 File No. 333-286783 REQUEST FOR ACCELERATION OF EFFECTIVENESS Requested Date: Thursday, May 1, 2025 Reque

Form of Warrant

Exhibit 4.1 WARRANT TO PURCHASE COMMON SHARES PINEAPPLE FINANCIAL INC. Warrant Shares: Initial Exercise Date: , 2025 Issue Date: , 2025 THIS WARRANT TO PURCHASE COMMON SHARES (the “Warrant”) certifies that, for value received, or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on or after the da

As filed with the Securities and Exchange Commission on May 1, 2025

As filed with the Securities and Exchange Commission on May 1, 2025 Registration No.

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables S-1 (Form Type) PINEAPPLE FINANCIAL INC.

As filed with the Securities and Exchange Commission on April 25, 2025

As filed with the Securities and Exchange Commission on April 25, 2025 Registration No.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 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 February 28, 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 FINANCIA

As confidentially submitted to the U.S. Securities and Exchange Commission on April [ ], 2025. This draft registration statement has not been publicly filed with the Securities and Exchange Commission and all information herein remains strictly confi

As confidentially submitted to the U.S. Securities and Exchange Commission on April [ ], 2025. This draft registration statement has not been publicly filed with the Securities and Exchange Commission and all information herein remains strictly confidential. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECUR

April 4,

April 4, 2025 VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street NE Washington, D.C. 20549 Re: Pineapple Financial Inc. (the “Company”) Draft Registration Statement on Form S-1 File No. 333- Filed April 4, 2025 Ladies and Gentlemen: The Company affirms that the above-referenced Registration Statement on Form S-1 (the “Registration Statement”) confidentia

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 7, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of inc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 27, 2025 PINEAPPLE FINAN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 27, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of

Company’s response to the Resignation Letter from Nima Besharat

Exhibit 17.2 Pineapple Financial Inc.’s Response to the Resignation Letter from Nima Besharat Following a thorough review of Nima Besharat’s actions as a director of Pineapple Financial Inc. (PAPL), the board of directors determined that his continued service was not in the best interest of the company and its shareholders. As such, it was decided that he would not be re-elected at the upcoming An

Resignation Letter from Nima Besharat

Exhibit 17.1 VIA EMAIL Dear Mr. Green, I am writing to hereby resign from the Board of Directors of Pineapple Financial (NYSE American: PAPL) effectively immediately due to serious corporate governance concerns surrounding how the company is managed as public company and your lack of leadership as Chairman of Pineapple Financial. 1) Mr. Dasgupta and Mr. Marin have repeatedly failed to seek assista

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 18, 2025 PINEAPPLE FINAN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 18, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 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 November 30, 2024 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 FINANCIA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING (Check One) ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: November 30, 2024 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F ☐ Transition Report on Form 11-K ☐ Transition Report on Form 10-Q For the Transition Peri

Insider Trading Policy

Exhibit 19.1 PINEAPPLE FINANCIAL INC. INSIDER TRADING POLICY This is a reminder about Pineapple Financial Inc’s (the “Company”) Insider Trading Policy and Trading Blackout Policy. All recipients of this memorandum are subject to the Company’s Insider Trading Policy and Trading Blackout Policy. Some of you — officers and directors — are subject to additional rules described in this memo. 1. General

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended August 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended August 31, 2024 ☐ 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

Clawback Policy

Exhibit 97.1 PINEAPPLE FINANCIAL INC. CLAWBACK POLICY (As adopted by the Board of Directors on [], 2024) 1. Introduction and Purpose 1.1 Introduction. This document sets forth the Clawback Policy (the “Policy”) of Pineapple Financial Inc. (the “Company,” which term as used in this Policy, unless the context otherwise requires, shall include its subsidiaries). 1.2 Purpose. The Company has establish

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549

OMB APPROVAL UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 OMB Number: 3235-0058 Expires: August 30, 2025 Estimated average burden hours per response............. 2.50 FORM 12b-25 SEC FILE NUMBER 001-41738 NOTIFICATION OF LATE FILING CUSIP NUMBER 72303K207 (Check one): ☒ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended:

Form of the Securities Purchase Agreement

Exhibit 10.1 FORM OF SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of November [*], 2024 between Pineapple Financial Inc., a corporation existing under the federal laws of Canada (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”).

Form of Placement Agent Warrant

Exhibit 10.3 FORM OF PLACEMENT AGENT WARRANT NEITHER THIS SECURITY NOR THE SECURITIES AS TO WHICH THIS SECURITY MAY BE EXERCISED HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EX

Pricing Press Release dated November 13, 2024

Exhibit 99.1

Form of Pre-Funded Warrant

Exhibit 10.2 FORM OF PRE-FUNDED COMMON SHARE PURCHASE WARRANT PINEAPPLE FINANCIAL INC. Warrant Shares: [*] Initial Exercise Date: [*], 2024 THIS PRE-FUNDED COMMON SHARE PURCHASE WARRANT (the “Warrant”) certifies that, for value received, [] or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on o

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 13, 2024 PINEAPPLE FINAN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 13, 2024 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of

382,667 Common Shares Pre-Funded Warrants to purchase 1,284,000 Common Shares (and the Common Shares underlying the Pre-Funded Warrants)

Filed Pursuant to Rule 424(b)(5) Registration No. 333-282629 Prospectus Supplement (to Prospectus dated October 29, 2024) 382,667 Common Shares Pre-Funded Warrants to purchase 1,284,000 Common Shares (and the Common Shares underlying the Pre-Funded Warrants) Pineapple Financial Inc. (the “Company” or “we” or “our” or “us”) is offering (“Offering”) 382,667 common shares (“Shares”), no par value per

PINEAPPLE FINANCIAL INC. Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1

PINEAPPLE FINANCIAL INC. Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1 October 28, 2024 Securities and Exchange Commission Division of Corporation Finance 100 F Street N.E. Washington, D.C. 20549 Attention: Mr. Robert Arzonetti Re: Pineapple Financial Inc. Registration Statement on Form S-3 (as amended) File No. 333-282629 Ladies and Gentlemen: Pursuant to Rule 461 promulgated under

Form of Indenture

Exhibit 4.3 PINEAPPLE FINANCIAL, INC., Issuer AND [TRUSTEE], Trustee INDENTURE Dated as of [•], 20 Debt Securities TABLE OF CONTENTS PAGE ARTICLE 1 DEFINITIONS 1 Section 1.01 Definitions of Terms 1 ARTICLE 2 ISSUE, DESCRIPTION, TERMS, EXECUTION, REGISTRATION AND EXCHANGE OF SECURITIES 5 Section 2.01 Designation and Terms of Securities 5 Section 2.02 Form of Securities and Trustee’s Certificate 8 S

As filed with the Securities and Exchange Commission on October 25, 2024

As filed with the Securities and Exchange Commission on October 25, 2024 Registration No.

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables FORM S-3 (Form Type) Pineapple Financial Inc.

As filed with the Securities and Exchange Commission on October 15, 2024

As filed with the Securities and Exchange Commission on October 15, 2024 Registration No.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 5, 2024 PINEAPPLE FINAN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 5, 2024 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 29, 2024 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 25, 2024 PINEAPPLE FINANCIAL

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 25, 2024 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of inc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 15, 2024 PINEAPPLE FINANCIAL

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 15, 2024 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of inc

Pineapple Financial Inc. Condensed Interim Consolidated Statements of Operations and Comprehensive Loss (Unaudited) For the three month and nine month periods ended May 31, 2024 (Expressed in US Dollars)

Exhibit 99.1 Pineapple Financial Inc. Announces 20.43 Percent Revenue Growth in Fiscal 2024 Third Quarter Ended May 31, 2024 TORONTO, July 15, 2024 – Pineapple Financial Inc. (NYSE American: PAPL), a leading tech-focused mortgage firm with an integrated network of partner brokerages and agents across Canada, today announced that, for its third 2024 fiscal quarter ended May 31, 2024, the company ac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 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, 2024 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

PINEAPPLE FINANCIAL INC. Up To 13,910,991 Common Shares

Filed pursuant to Rule 424(b)(3) Registration No. 333-279802 PROSPECTUS PINEAPPLE FINANCIAL INC. Up To 13,910,991 Common Shares This prospectus relates to up to 13,910,991 common shares, no par value (the “Common Shares”), of Pineapple Financial Inc. (the “Company”, “we”, “us”, “our”, “Pineapple”), that the selling security holder identified in this prospectus (the “Selling Shareholder”) may sell

July 3, 2024

July 3, 2024 VIA EDGAR AND FACSIMILE United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F.

As filed with the Securities and Exchange Commission on June 26, 2024

As filed with the Securities and Exchange Commission on June 26, 2024 Registration No.

Securities and Exchange Commission

June 26, 2024 Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, D.

As filed with the Securities and Exchange Commission on June 20, 2024

As filed with the Securities and Exchange Commission on June 20, 2024 Registration No.

Securities and Exchange Commission

June 20, 2024 Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, D.

As filed with the Securities and Exchange Commission on May 29, 2024

As filed with the Securities and Exchange Commission on May 29, 2024 Registration No.

Filing Fee Table

EXHIBIT 107 Calculation of Filing Fee Tables Form S-1 Pineapple Financial Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price(1) Fee Rate Amount of Registration Fee Newl

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 10, 2024 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of inco

Equity Purchase Agreement dated May 10, 2024

Exhibit 10.1

Registration Rights Agreement dated May 10, 2024

Exhibit 10.2

Securities Purchase Agreement dated May 10, 2024

Exhibit 10.3

Convertible Promissory Note

Exhibit 10.4

Form of Warrant

Exhibit 4.1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 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 February 29, 2024 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 FINANCIA

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 29, 2024 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 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 November 30, 2023 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 FINANCIA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended August 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended August 31, 2023 ☐ 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

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549

OMB APPROVAL UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 OMB Number: 3235-0058 Expires: August 30, 2025 Estimated average burden hours per response............. 2.50 FORM 12b-25 SEC FILE NUMBER 001-41738 NOTIFICATION OF LATE FILING CUSIP NUMBER 72303K207 (Check one): ☒ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended:

Press Release dated November 3, 2023

Exhibit 99.2

Press Release dated October 31, 2023

Exhibit 99.1

Entry into a Material Definitive Agreement, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 31, 2023 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable (State or other jurisdiction (Commission (IRS Employer of

Underwriting Agreement between Pineapple Financial Inc and EF Hutton

Exhibit 1.1 UNDERWRITING AGREEMENT between PINEAPPLE FINANCIAL INC. and EF HUTTON, division of Benchmark Investments, LLC, as Representative of the Several Underwriters UNDERWRITING AGREEMENT between PINEAPPLE FINANCIAL INC. and EF HUTTON, division of Benchmark Investments, LLC, as Representative of the Several Underwriters New York, New York October 31, 2023 EF HUTTON, division of Benchmark Inves

PINEAPPLE FINANCIAL INC. 875,000 Common Shares

Filed pursuant to Rule 424(b)(4) Registration No. 333-268636 PINEAPPLE FINANCIAL INC. 875,000 Common Shares This is an initial public offering of 875,000 common shares, no par value (each, a “Common Share”, and together, the “Common Shares”), of Pineapple Financial Inc. (the “Company”, “we”, “us”, “our”, “Pineapple”). The initial public offering price of our common shares is $4.00 per share. Prior

October 10, 2023

October 10, 2023 VIA EDGAR AND FACSIMILE United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F.

EF Hutton, division of Benchmark Investments, LLC 590 Madison Avenue, 39th Floor New York, NY 10022

EF Hutton, division of Benchmark Investments, LLC 590 Madison Avenue, 39th Floor New York, NY 10022 October 10, 2023 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Trade & Services 100 F Street, N.

As filed with the Securities and Exchange Commission on September 28, 2023

As filed with the Securities and Exchange Commission on September 28, 2023 Registration No.

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046 September 27, 2023 VIA EDGAR Susan Block Division of Corporation Finance Securities and Exchange Commission 100 F Street, NE Washington, D.C. 20549 Re: Re: Pineapple Financial Inc. Amendment No. 5 to Registration Statement on Form S-1 Filed on September 15, 2023 File No. 333-268636 Dear Ms. Block,

Filing Fee Table

EXHIBIT 107 Calculation of Filing Fee Tables Form S-1 Pineapple Financial Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price(1) Fee Rate Amount of Registration Fee Newl

As filed with the Securities and Exchange Commission on September 15, 2023

As filed with the Securities and Exchange Commission on September 15, 2023 Registration No.

EF Hutton, division of Benchmark Investments, LLC 590 Madison Avenue, 39th Floor New York, NY 10022

EF Hutton, division of Benchmark Investments, LLC 590 Madison Avenue, 39th Floor New York, NY 10022 July 6, 2023 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 PINEAPPLE FINANCIAL INC. (Exact name of registr

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in its charter) Canada Not applicable (State or incorporation or organization) (I.R.S. Employer Identification No.) Unit 200, 111 Gor

July 6, 2023

July 6, 2023 VIA EDGAR AND FACSIMILE United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F.

EF Hutton, division of Benchmark Investments, LLC 590 Madison Avenue, 39th Floor New York, NY 10022

EF Hutton, division of Benchmark Investments, LLC 590 Madison Avenue, 39th Floor New York, NY 10022 July 6, 2023 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Trade & Services 100 F Street, N.

VIA EDGAR

July 6, 2023 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street N.

As filed with the Securities and Exchange Commission on July 5, 2023

As filed with the Securities and Exchange Commission on July 5, 2023 Registration No.

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046 July 5, 2023 VIA EDGAR Tonya Aldave Division of Corporation Finance Securities and Exchange Commission 100 F Street, NE Washington, D.C. 20549 Re: Re: Pineapple Financial Inc. Amendment No. 3 to Registration Statement on Form S-1 Filed on June 21, 2023 File No. 333-268636 Dear Ms. Aldave, On behalf

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046 July 3, 2023 VIA EDGAR Susan Block Division of Corporation Finance Securities and Exchange Commission 100 F Street, NE Washington, D.C. 20549 Re: Re: Pineapple Financial Inc. Amendment No. 2 to Registration Statement on Form S-1 Filed on May 16, 2023 File No. 333-268636 Dear Ms. Block, On behalf of

Nominating and Corporate Governance Committee Charter

Exhibit 99.3

Code of Ethics

Exhibit 14.1 Pineapple FINANCIAL Inc. Code of Ethics and Business Conduct 1. Introduction. 1.1 The Board of Directors of Pineapple Financial Inc. (the “Company”), has adopted this Code of Ethics and Business Conduct (the “Code”) in order to: (a) promote honest and ethical conduct, including the ethical handling of actual or apparent conflicts of interest; (b) promote full, fair, accurate, timely a

As filed with the Securities and Exchange Commission on June 21, 2023

As filed with the Securities and Exchange Commission on June 21, 2023 Registration No.

Compensation Committee Charter

Exhibit 99.2

Audit Committee Charter

Exhibit 99.1

List of Subsidiaries of the Registrant

Exhibit 21.1 List of Subsidiaries Pineapple Financial, Inc. Subsidiary Name Jurisdiction of Organization Percentage Owned Pineapple Insurance Inc. Ontario, Canada 100% Pineapple National Inc. Ontario, Canada 100%

Employment Agreement, dated April 4, 2023 between the Company and Sarfraz Habib

Exhibit 10.3 EXECUTIVE EMPLOYMENT OFFER LETTER April 4, 2023 Re: Offer Letter Dear Sarfraz, On behalf of Pineapple Financial Inc. (the “Company”), I am pleased to offer you employment with Pineapple Financial Inc. in the position of Chief Financial Officer, starting on April 10, 2023. In that position, you will report to Shubha Dasgupta, Chief Executive Officer. During your employment, you will be

Stock Option Plan

Exhibit 10.1 PINEAPPLE FINANCIAL INC. 2022 OMNIBUS EQUITY INCENTIVE COMPENSATION PLAN ARTICLE 1 ESTABLISHMENT, PURPOSE AND DURATION 1.1 Establishment of the Plan. The following is the 2022 Omnibus Equity Incentive Compensation Plan (the “Plan”) of PINEAPPLE FINANCIAL INC. (the “Company”) pursuant to which stock-based compensation Awards (as defined below) may be granted to eligible Participants (a

As filed with the Securities and Exchange Commission on May 16, 2023

As filed with the Securities and Exchange Commission on May 16, 2023 Registration No.

Salesforce Agreement, between the Company and Salesforce.com, dated December 1, 2020

Exhibit 10.2

Articles of Continuance

Exhibit 3.1 Schedule / Annexe Restrictions on Share Transfers / Restrictions sur le transfert des actions Board Approval - While the Corporation is not a public company, no shares shall be transferred without the prior consent of the directors expressed by a resolution of the board of directors and the directors shall not be required to give any reason for refusing to consent to any proposed trans

Form of Representative’s Warrant (included in Exhibit 1.1)

Exhibit 1.1 UNDERWRITING AGREEMENT between PINEAPPLE FINANCIAL INC. and EF HUTTON, division of Benchmark Investments, LLC, as Representative of the Several Underwriters UNDERWRITING AGREEMENT between PINEAPPLE FINANCIAL INC. and EF HUTTON, division of Benchmark Investments, LLC, as Representative of the Several Underwriters New York, New York [●], 2023 EF Hutton, division of Benchmark Investments,

Form of Mortgage Broker Affiliation Agreement

Exhibit 10.4 MORTGAGE BROKERAGE AFFILIATION AGREEMENT THIS AGREEMENT is made effective on the day of , BETWEEN: 2487269 ONTARIO LIMITED (o/a Capital Lending Centre(s)), an Ontario corporation with its registered office at 200-111 Gordon Baker Road, North York, Ontario, M2H 3R1 (the “Company”) - and - [*] (the “Affiliate Broker”) 1. BACKGROUND 1.1. The Affiliate Broker is a licensed mortgage broker

Bylaws incorporated by reference to Exhibit 3.2 to the Company’s Amendment to the Registration Statement on Form S-1 (No. 333-268636) filed with the Securities and Exchange Commission on September 28, 2023.

Exhibit 3.2 BY-LAW NO. 1 A by-law relating generally to the conduct of the business and affairs of: PINEAPPLE FINANCIAL INC. (hereinafter called the “Corporation”) IT IS HEREBY ENACTED as a by-law of the Corporation as follows: 1. INTERPRETATION 1.01 In the by-laws of the Corporation, unless the context otherwise specifies or requires: (a) “CBCA” means the Canada Business Corporations Act, as from

Salesforce Agreement, between the Company and Salesforce.com, dated December 1, 2020

Exhibit 10.2

Employment Agreement, dated October 18, 2021, between the Company and Rupen Shah

Exhibit 10.3 EXECUTIVE EMPLOYMENT AGREEMENT THIS AGREEMENT dated as October 18, 2021 BETWEEN: (the “Executive”) Rupen Shah A N D (the “Employer”) PINEAPPLE FINANCIAL INC. o/a PINEAPPLE WHEREAS the Employer wishes to retain the services of the Executive and the Executive wishes to accept employment with the Employer, all in accordance with the provisions of this Agreement; NOW THEREFORE for good an

Form of Representative’s Warrant (included in Exhibit 1.1)

EX-1.1 2 ex1-1.htm Exhibit 1.1 UNDERWRITING AGREEMENT between PINEAPPLE FINANCIAL INC. and EF HUTTON, division of Benchmark Investments, LLC, as Representative of the Several Underwriters UNDERWRITING AGREEMENT between PINEAPPLE FINANCIAL INC. and EF HUTTON, division of Benchmark Investments, LLC, as Representative of the Several Underwriters New York, New York [●], 2022 EF Hutton, division of Ben

Form of Mortgage Broker Affiliation Agreement

Exhibit 10.4 MORTGAGE BROKERAGE AFFILIATION AGREEMENT THIS AGREEMENT is made effective on the day of , BETWEEN: 2487269 ONTARIO LIMITED (o/a Capital Lending Centre(s)), an Ontario corporation with its registered office at 200-111 Gordon Baker Road, North York, Ontario, M2H 3R1 (the “Company”) - and - [*] (the “Affiliate Broker”) 1. BACKGROUND 1.1. The Affiliate Broker is a licensed mortgage broker

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046 January 4, 2023 VIA EDGAR Susan Block Division of Corporation Finance Securities and Exchange Commission 100 F Street, NE Washington, D.C. 20549 Re: Re: Pineapple Financial Inc. Registration Statement on Form S-1 Filed on December 1, 2022 File No. 333-268636 Dear Ms. Block, On behalf of Pineapple F

List of Subsidiaries of the Registrant

Exhibit 21.1 List of Subsidiaries Pineapple Financial, Inc. Subsidiary Name Jurisdiction of Organization Percentage Owned Pineapple Insurance Inc. Ontario, Canada 100% Pineapple National Inc. Ontario, Canada 100%

As filed with the Securities and Exchange Commission on January 4, 2023

As filed with the Securities and Exchange Commission on January 4, 2023 Registration No.

As filed with the Securities and Exchange Commission on December 1, 2022

As filed with the Securities and Exchange Commission on December 1, 2022 Registration No.

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046 December 1, 2022 VIA EDGAR Susan Block Division of Corporation Finance Securities and Exchange Commission 100 F Street, NE Washington, D.C. 20549 Re: Pineapple Financial Inc. Amendment No. 1 to Draft Registration Statement on Form S-1 Submitted on October 12, 2022 CIK No. 0001938109 Dear Ms. Block,

Filing Fee Table

EXHIBIT 107 Calculation of Filing Fee Tables Form S-1 Innovation Beverage Group Limited (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price(1) Fee Rate Amount of Registration Fee Newly Registered Securities Fees to Be Paid Equity Common shares Rule 457(o) $ $ 17,250,000 0.

As confidentially submitted to the Securities and Exchange Commission on October 12, 2022

DRS/A 1 filename1.htm As confidentially submitted to the Securities and Exchange Commission on October 12, 2022 Registration No. 333-[ ] UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 1 to FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter) Ontario, Canada 6199 Not ap

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046

PINEAPPLE FINANCIAL INC. Unit 200 111 Gordon Baker Road Toronto, Ontario M2H 3R1 Tel: (416) 669-2046 October 12, 2022 VIA EDGAR Susan Block Division of Corporation Finance Securities and Exchange Commission 100 F Street, NE Washington, D.C. 20549 Re: Re: Pineapple Financial Inc. Draft Registration Statement on Form S-1 Submitted on September 1, 2022 CIK No. 0001938109 Dear Ms. Block, On behalf of

As confidentially submitted to the Securities and Exchange Commission on September 1, 2022

DRS 1 filename1.htm As confidentially submitted to the Securities and Exchange Commission on September 1, 2022 Registration No. 333-[ ] UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter) Ontario, Canada 6199 Not applicable (State or O