PAPLF / Pineapple Financial Inc. - SEC申報文件,年度報告,委任書

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CIK 1938109
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Pineapple Financial Inc.
SEC Filings (Chronological Order)
本頁面提供了一個完整的、按時間順序排列的美國證券交易委員會(SEC)申報文件列表,不包括我們在其他地方提供的所有權申報。
June 3, 2026 8-K

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 31, 2026 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): May 31, 2026 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

June 3, 2026 EX-16.1

June 3, 2026

Exhibit 16.1 June 3, 2026 Office of the Chief Accountant Securities and Exchange Commission 460 Fifth Street N. W. Washington, DC 20549 Re: Pineapple Financial Inc. Commission File Number 001-41738 Dear Sirs: We have received a copy of, and are in agreement with, the statements being made by Pineapple Financial Inc. in Item 4.01 of its Form 8-K dated June 3, 2026, captioned “Changes in Registrant’

April 22, 2026 EX-99.2

EX-99.2

Exhibit 99.2

April 22, 2026 EX-99.1

PINEAPPLE FINANCIAL ANNOUNCES EXPANDED $15 MILLION SHARE REPURCHASE PROGRAM Expanded Buyback Signals Management’s Commitment to Long-Term Value; Repurchases to Commence Immediately

Exhibit 99.1 PINEAPPLE FINANCIAL ANNOUNCES EXPANDED $15 MILLION SHARE REPURCHASE PROGRAM Expanded Buyback Signals Management’s Commitment to Long-Term Value; Repurchases to Commence Immediately Toronto, Ontario, April 22, 2026 - Pineapple Financial Inc. (NYSE American: PAPL), (“Pineapple” or “the Company”), a leading fintech platform, today announced that its Board of Directors has approved an exp

April 22, 2026 8-K

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): April 22, 2026 PINEAPPLE FINANCIA

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): April 22, 2026 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable 00-0000000 (State or other jurisdiction (Commission (IRS Emp

April 13, 2026 10-Q

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, 2026 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

March 18, 2026 8-K

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 13, 2026 PINEAPPLE FINANCIA

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 13, 2026 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable 00-0000000 (State or other jurisdiction (Commission (IRS Emp

February 10, 2026 EX-10.3

DIRECTOR AGREEMENT

Exhibit 10.3 DIRECTOR AGREEMENT This DIRECTOR AGREEMENT (this “Agreement”), [ ] (the “Effective Date”), is entered into by and between Pineapple Financial Inc. (the “Company”), and Drew Green (the “Chairman”). The parties are sometimes individually referred to as “Party” and collectively as “Parties.” PRELIMINARY STATEMENTS WHEREAS, the Company currently carries on the business of providing mortga

February 10, 2026 EX-10.2

EMPLOYMENT AGREEMENT

Exhibit 10.2 EMPLOYMENT AGREEMENT THIS AGREEMENT dated as of the [ ] day of [ ] 2026 (the “Effective Date”). BETWEEN: PINEAPPLE FINANCIAL INC, a mortgage broker in the City of Toronto, having its principal place of business at 111 Gordon Baker Road, Suite 200, North York, ON M2H 3R1. (the “Employer” or the “Company”) AND: Kendall Marin (the “Executive”) WHEREAS, The Company desires for the Executi

February 10, 2026 8-K

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 5, 2026 PINEAPPLE FINANC

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 5, 2026 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 Not applicable 00-0000000 (State or other jurisdiction (Commission (IRS E

February 10, 2026 EX-10.1

EMPLOYMENT AGREEMENT

Exhibit 10.1 EMPLOYMENT AGREEMENT THIS AGREEMENT dated as of the [ ] day of [ ] 2026 (the “Effective Date”). BETWEEN: PINEAPPLE FINANCIAL INC, a mortgage broker in the City of Toronto, having its principal place of business at 111 Gordon Baker Road, Suite 200, North York, ON M2H 3R1. (the “Employer” or the “Company”) AND: Shubha Dasgupta (the “Executive”) WHEREAS, The Company desires for the Execu

February 6, 2026 DEF 14A

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

January 21, 2026 EX-FILING FEES

Calculation of Filing Fee Table FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 (Form Type) PINEAPPLE FINANCIAL INC. (Exact Name of Registrant As Specified in its Charter) Table 1: Newly Registered Securities

Exhibit 107 Calculation of Filing Fee Table FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 (Form Type) PINEAPPLE FINANCIAL INC.

January 21, 2026 10-Q

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, 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

January 21, 2026 S-8

As filed with the Securities and Exchange Commission on January 21, 2026

As filed with the Securities and Exchange Commission on January 21, 2026 Registration No.

January 15, 2026 NT 10-Q

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, 2025 ☐ 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

December 29, 2025 8-K

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): December 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): December 18, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 00-0000000Not applicable (State or other jurisdiction (Commission (IRS E

December 12, 2025 EX-10.21

MASTER LOAN AND SECURITY AGREEMENT

Exhibit 10.21 MASTER LOAN AND SECURITY AGREEMENT This Master Loan and Security Agreement (this “Agreement”) is made and entered into as of the Effective Date provided herein, by and between Voltedge Ltd. (“Lender”) and Pineapple Financial Inc., an Ontario corporation (“Borrower,” together with Lender, the “Parties” and each individually a “Party”). This Agreement includes the Standard Terms and Co

December 12, 2025 EX-FILING FEES

Calculation of Filing Fee Tables Form S-1 (Form Type) PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter)

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

December 12, 2025 S-1

As filed with the Securities and Exchange Commission on December 12, 2025

As filed with the Securities and Exchange Commission on December 12, 2025 Registration No.

December 12, 2025 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended August 31, 2025 ☐ TRANSITION REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended August 31, 2025 ☐ 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 F

December 12, 2025 EX-4.1

COMMON SHARE PURCHASE WARRANT PINEAPPLE FINANCIAL INC.

Exhibit 4.1 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE 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 EXCEPT PURSUANT TO AN EFFECTIVE REGISTR

December 9, 2025 EX-10.3

AMENDMENT TO REGISTRATION RIGHTS AGREEMENT

Exhibit 10.3 SECOND AMENDMENT TO REGISTRATION RIGHTS AGREEMENT This Second Amendment to the Registration Rights Agreement (this “Second Amendment”) is made and entered into as of December 5, 2025, by and among Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Company”) and each investor (each, including its successors and assigns, an “I

December 9, 2025 EX-10.2

FIFTH AMENDMENT SECURITIES PURCHASE AGREEMENT

Exhibit 10.2 FIFTH AMENDMENT TO SECURITIES PURCHASE AGREEMENT This Fifth Amendment to Securities Purchase Agreement (this “Fifth Amendment”) is made and entered into as of December 5, 2025, by and among Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Company”) and each purchaser (each, including its successors and assigns, a “Purchase

December 9, 2025 8-K

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): December 3, 2025 PINEAPPLE FINANC

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): December 3, 2025 PINEAPPLE FINANCIAL INC. (Exact name of registrant as specified in charter) Canada 001-41738 00-0000000 Not applicable (State or other jurisdiction (Commission (IRS E

December 9, 2025 EX-10.1

FOURTH AMENDMENT SECURITIES PURCHASE AGREEMENT

Exhibit 10.1 FOURTH AMENDMENT TO SECURITIES PURCHASE AGREEMENT This Fourth Amendment to Securities Purchase Agreement (this “Fourth Amendment”) is made and entered into as of December 3, 2025, by and among Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Company”) and each purchaser (each, including its successors and assigns, a “Purch

December 3, 2025 10-K

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, 2025 ☐ 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, 2025 ☐ 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

December 1, 2025 NT 10-K

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:

November 12, 2025 8-K

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 7, 2025 PINEAPPLE FINANC

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 7, 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 E

November 12, 2025 EX-10.1

THIRD AMENDMENT TO SECURITIES PURCHASE AGREEMENT

Exhibit 10.1 THIRD AMENDMENT TO SECURITIES PURCHASE AGREEMENT This Third Amendment to Securities Purchase Agreement (this “Third Amendment”) is made and entered into as of November 7, 2025, by and among Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Company”) and each purchaser (each, including its successors and assigns, a “Purchase

November 12, 2025 EX-10.2

FIRST AMENDMENT REGISTRATION RIGHTS AGREEMENT

Exhibit 10.2 FIRST AMENDMENT TO REGISTRATION RIGHTS AGREEMENT This First Amendment to the Registration Rights Agreement (this “First Amendment”) is made and entered into as of November 7, 2025, by and among Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Company”) and each investor (each, including its successors and assigns, an “Inve

November 4, 2025 8-K

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, 2025 PINEAPPLE FINANC

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, 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

November 4, 2025 EX-10.1

SECOND AMENDMENT SECURITIES PURCHASE AGREEMENT

Exhibit 10.1 SECOND AMENDMENT TO SECURITIES PURCHASE AGREEMENT This Second Amendment to Securities Purchase Agreement (this “ Second Amendment”) is made and entered into as of November 3, 2025, by and among Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Company”) and each purchaser (each, including its successors and assigns, a “Purc

October 6, 2025 EX-10.1

International Swaps and Derivatives Association, Inc. 2002 MASTER AGREEMENT dated as of September 30, 2025

Exhibit 10.1 International Swaps and Derivatives Association, Inc. 2002 MASTER AGREEMENT dated as of September 30, 2025 FalconX Bravo, Inc and Pineapple Financial Inc. have entered and/or anticipate entering into one or more transactions (each a “Transaction”) that are or will be governed by this 2002 Master Agreement, which includes the schedule (the “Schedule”), and the documents and other confi

October 6, 2025 EX-10.3

International Swaps and Derivatives Association, Inc. CREDIT SUPPORT ANNEX to the Schedule to the 2002 Master Agreement dated as of September 30, 2025 FalconX Bravo, Inc. (“Party A”), Pineapple Financial Inc. (“Party B”)

Exhibit 10.3 (Bilateral Form) (ISDA Agreements Subject to New York Law Only) International Swaps and Derivatives Association, Inc. CREDIT SUPPORT ANNEX to the Schedule to the 2002 Master Agreement dated as of September 30, 2025 between FalconX Bravo, Inc. (“Party A”), and Pineapple Financial Inc. (“Party B”) This Annex supplements, forms part of, and is subject to, the above-referenced Agreement,

October 6, 2025 EX-10.2

International Swaps and Derivatives Association, Inc. to the 2002 Master Agreement dated as of September 30, 2025 FalconX Bravo, Inc., a corporation organized and existing under the laws of Delaware, (“Party A”), Pineapple Financial Inc, a Corporatio

Exhibit 10.2 International Swaps and Derivatives Association, Inc. SCHEDULE to the 2002 Master Agreement dated as of September 30, 2025 between FalconX Bravo, Inc., a corporation organized and existing under the laws of Delaware, (“Party A”), and Pineapple Financial Inc, a Corporation organized and existing under the laws of Canada (“Party B”) Part 1 Termination Provisions (1) (a) “Specified Entit

October 6, 2025 8-K

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 30, 2025 PINEAPPLE FINA

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 30, 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

September 30, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(c) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(c) 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 Statement ☐ Definitive Additional Materials ☐ Soliciting Material under §240.

September 29, 2025 PRER14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Amendment No. 1 Proxy Statement Pursuant to Section 14(c) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Amendment No.

September 29, 2025 LETTER

LETTER

September 29, 2025 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc.

September 29, 2025 CORRESP

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 29, 2025 VIA EDGAR Robert Arzonetti Division of Corporation Finance Securities and Exchange Commission 100 F Street, NE Washington, D.C. 20549 Re: Re: Pineapple Financial Inc. Preliminary Proxy Statement on Schedule 14A Filed September 19, 2025 File No. 001-41738 Dear Mr. Arzonetti, On be

September 26, 2025 LETTER

LETTER

September 26, 2025 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc.

September 19, 2025 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(c) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(c) 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 Statement ☐ Definitive Additional Materials ☐ Soliciting Material under §240.

September 17, 2025 D

D

X0708 D LIVE 0001938109 Pineapple Financial Inc. UNIT 200 111 GORDON BAKER ROAD NORTH YORK A6 ONTARIO, CANADA M2H 3RI (416) 669-2046 BRITISH COLUMBIA, CANADA None None Corporation true Shubha Dasgupta Unit 200 111 Gordon Baker Road City North York North York A6 ONTARIO, CANADA M2H 3RI Executive Officer Director Sarfraz Habib Unit 200 111 Gordon Baker Road City North York North York A6 ONTARIO, CAN

September 10, 2025 EX-10.1

SECURITIES PURCHASE AGREEMENT

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of September 1, 2025, between Pineapple Financial Inc. (the “Company”), a corporation continued and existing under the Canada Business Corporations Act, and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively, t

September 10, 2025 EX-10.2

REGISTRATION RIGHTS AGREEMENT

Exhibit 10.2 REGISTRATION RIGHTS AGREEMENT THIS REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of September 2, 2025, is entered into by and among Pineapple Financial Inc., (the “Company”), a corporation continued and existing under the Canada Business Corporations Act (the “CBCA”), and the several investors signatory hereto (each individually, an “Investor” and collectively, together w

September 10, 2025 EX-10.7

COMMON STOCK PURCHASE AGREEMENT

Exhibit 10.7 COMMON STOCK PURCHASE AGREEMENT This Common Stock Purchase Agreement (this “Agreement”) is entered into effective as August [-], 2025 (the “Execution Date”), by and between Pineapple Financial Inc., a Canada company (the “Company”), and White Lion Capital, LLC, a Nevada limited liability company (the “Investor”). WHEREAS, the parties desire that, upon the terms and subject to the cond

September 10, 2025 EX-10.10

LOCK-UP AGREEMENT

Exhibit 10.10 LOCK-UP AGREEMENT September 4, 2025 Re: Securities Purchase Agreement, dated as of September 2, 2025 (the “Purchase Agreement”), between Pineapple Financial Inc. (the “Company”) and the purchasers signatory thereto (each, a “Purchaser” and, collectively, the “Purchasers”) Ladies and Gentlemen: Capitalized terms not otherwise defined in this letter agreement (this “Letter Agreement”)

September 10, 2025 EX-99.1

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

September 10, 2025 EX-10.8

PLACEMENT AGENCY AGREEMENT

Exhibit 10.8 PLACEMENT AGENCY AGREEMENT September 4, 2025 Pineapple Financial, Inc, Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1 Ladies and Gentlemen: Introductory. This Placement Agency Agreement the (“Agreement”) sets forth the terms upon which D. Boral Capital LLC (“D. Boral” or the “Placement Agent”), shall be engaged by Pineapple Financial Inc. (the “Company”), a corporation co

September 10, 2025 EX-10.4

PINEAPPLE FINANCIAL INC. -and - ODYSSEY TRANSFER AND TRUST COMPANY -and - D. BORAL CAPITAL LLC SUBSCRIPTION RECEIPT AGREEMENT Providing for the Issue of Subscription Receipts of Pineapple Financial Inc. Dated as of September 4, 2025

Exhibit 10.4 PINEAPPLE FINANCIAL INC. -and - ODYSSEY TRANSFER AND TRUST COMPANY -and - D. BORAL CAPITAL LLC SUBSCRIPTION RECEIPT AGREEMENT Providing for the Issue of Subscription Receipts of Pineapple Financial Inc. Dated as of September 4, 2025 TABLE OF CONTENTS ARTICLE 1 INTERPRETATION 2 1.1 Definitions 2 1.2 Interpretation 8 1.3 Applicable Law 8 ARTICLE 2 THE SUBSCRIPTION RECEIPTS 9 2.1 Creatio

September 10, 2025 EX-99.3

EX-99.3

Exhibit 99.3

September 10, 2025 EX-10.11

September 4, 2025

Exhibit 10.11 September 4, 2025 INJECTIVE FOUNDATION [*] Re: Pineapple Financial INJ Digital Asset Treasury Transaction Ladies and Gentlemen: Reference is made to the Securities Purchase Agreement, dated as of September 2, 2025 (the “SPA”), by and among Pineapple Financial, Inc., a corporation existing under the Canada Business Corporations Act (the “Company”) and the purchasers (as set forth on t

September 10, 2025 EX-99.2

Investor Relations

Exhibit 99.2 Investor Relations Pineapple Financial Closes $100 Million Private Placement and Initiates Injective Digital Asset Treasury Strategy, Becoming the First Publicly Traded INJ Holder on a National Exchange Published on 05 Sep 2025 INJ, the native asset of Injective, the leading finance focused blockchain, offers one of the highest staking yields in the industry and is designed to power n

September 10, 2025 EX-10.5

ASSET MANAGEMENT AGREEMENT

Exhibit 10.5 ASSET MANAGEMENT AGREEMENT This ASSET MANAGEMENT AGREEMENT (this “Agreement”), effective September 4, 2025 (the “Effective Date”), is entered into by and between Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Client”), and Canary Capital Group LLC, a Delaware limited liability company (the “Asset Manager” and, together w

September 10, 2025 EX-10.6

TRADING ADVISORY AGREEMENT

Exhibit 10.6 TRADING ADVISORY AGREEMENT This TRADING ADVISORY AGREEMENT (this “Agreement”), effective as of this 4th day of September 2025, is between Monarq Asset Management LLC, a Delaware limited liability company (the “Advisor”), and Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Client”). RECITALS The Client wishes to retain the

September 10, 2025 8-K

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 4, 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 4, 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

September 10, 2025 EX-10.3

FIRST AMENDMENT SECURITIES PURCHASE AGREEMENT

Exhibit 10.3 FIRST AMENDMENT TO SECURITIES PURCHASE AGREEMENT This First Amendment to Securities Purchase Agreement (this “Amendment”) is made and entered into as of September 4, 2025, by and among Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Company”) and each purchaser (each, including its successors and assigns, a “Purchaser” an

September 10, 2025 EX-10.9

VOTING AGREEMENT

Exhibit 10.9 VOTING AGREEMENT This VOTING AGREEMENT (this “Agreement”), dated as of September 4, 2025, is by and among Injective Foundation (“Injective”), Pineapple Financial Inc., a corporation continued and existing under the Canada Business Corporations Act (the “Company”), and the undersigned shareholders, officers and directors of the Company (each, a “Shareholder” and, collectively, the “Sha

September 2, 2025 8-K

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

September 2, 2025 EX-99.1

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

August 1, 2025 8-K

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

July 14, 2025 10-Q

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

June 27, 2025 8-K

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

May 27, 2025 DEF 14A

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

May 19, 2025 EX-99.1

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

May 19, 2025 8-K

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

May 15, 2025 PRE 14A

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

May 6, 2025 EX-99.1

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

May 6, 2025 8-K

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

May 6, 2025 EX-99.2

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 $

May 6, 2025 EX-4.1

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

May 6, 2025 EX-1.1

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

May 5, 2025 424B4

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

May 1, 2025 EX-10.9

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

May 1, 2025 EX-4.1

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

May 1, 2025 CORRESP

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

May 1, 2025 S-1/A

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.

May 1, 2025 EX-4.2

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

May 1, 2025 EX-1.1

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

May 1, 2025 CORRESP

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

April 25, 2025 EX-FILING FEES

Filing Fee Table

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

April 25, 2025 S-1

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.

April 16, 2025 LETTER

LETTER

April 16, 2025 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc. Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1 Re: Pineapple Financial Inc. Draft Registration Statement on Form S-1 Submitted April 4, 2025 CIK No. 0001938109 Dear Shubha Dasgupta: This is to advise you that we have not reviewed and will not review your registration statement. Please refer to Rules 460 an

April 14, 2025 10-Q

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

April 4, 2025 DRSLTR

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

April 4, 2025 DRS

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

March 10, 2025 8-K

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

February 27, 2025 8-K

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

February 25, 2025 EX-17.2

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

February 25, 2025 EX-17.1

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

February 25, 2025 8-K

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

February 21, 2025 DEFA14A

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

February 21, 2025 DEF 14A

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

January 21, 2025 10-Q

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

January 14, 2025 NT 10-Q

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

December 20, 2024 EX-97.1

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

December 20, 2024 10-K

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

December 20, 2024 EX-19.1

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

November 29, 2024 NT 10-K

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:

November 19, 2024 EX-10.1

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”).

November 19, 2024 EX-10.2

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

November 19, 2024 8-K

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

November 19, 2024 EX-99.1

Pricing Press Release dated November 13, 2024

Exhibit 99.1

November 19, 2024 EX-10.3

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

November 14, 2024 424B5

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

October 28, 2024 CORRESP

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

October 25, 2024 S-3/A

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.

October 25, 2024 EX-4.3

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

October 23, 2024 LETTER

LETTER

October 23, 2024 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc. Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1 Re: Pineapple Financial Inc. Registration Statement on Form S-3 Filed October 15, 2024 File No. 333-282629 Dear Shubha Dasgupta: This is to advise you that we have not reviewed and will not review your registration statement. Please refer to Rules 460 and 46

October 15, 2024 EX-FILING FEES

Filing Fee Table

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

October 15, 2024 S-3

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.

September 11, 2024 8-K

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

August 8, 2024 8-K/A

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

July 30, 2024 8-K

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

July 16, 2024 8-K

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

July 16, 2024 EX-99.1

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

July 15, 2024 10-Q

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

July 10, 2024 424B3

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 CORRESP

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.

June 26, 2024 LETTER

LETTER

United States securities and exchange commission logo June 26, 2024 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc.

June 26, 2024 CORRESP

Securities and Exchange Commission

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

June 26, 2024 S-1/A

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.

June 20, 2024 CORRESP

Securities and Exchange Commission

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

June 20, 2024 S-1/A

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.

June 17, 2024 LETTER

LETTER

United States securities and exchange commission logo June 17, 2024 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc.

May 29, 2024 S-1

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.

May 29, 2024 EX-FILING FEES

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

May 16, 2024 EX-10.2

Registration Rights Agreement dated May 10, 2024

Exhibit 10.2

May 16, 2024 EX-4.1

Form of Warrant

Exhibit 4.1

May 16, 2024 EX-10.3

Securities Purchase Agreement dated May 10, 2024

Exhibit 10.3

May 16, 2024 8-K

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

May 16, 2024 EX-10.4

Convertible Promissory Note

Exhibit 10.4

May 16, 2024 EX-10.1

Equity Purchase Agreement dated May 10, 2024

Exhibit 10.1

April 15, 2024 10-Q

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

March 5, 2024 8-K

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

February 8, 2024 DEFA14A

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

February 7, 2024 DEFA14A

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

February 5, 2024 DEF 14A

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

January 16, 2024 10-Q

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

December 14, 2023 10-K

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

November 30, 2023 NT 10-K

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:

November 6, 2023 EX-99.1

Press Release dated October 31, 2023

Exhibit 99.1

November 6, 2023 EX-1.1

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

November 6, 2023 8-K

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

November 6, 2023 EX-99.2

Press Release dated November 3, 2023

Exhibit 99.2

November 2, 2023 424B4

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 26, 2023 CERT

NYSE AMERICAN CERTIFICATION

New York Stock Exchange 11 Wall Street New York, NY 10005 Tel: +1 212.656.3000 nyse.com October 26, 2023 Chief, Information Technology Securities and Exchange Commission Division of Corporate Finance 100 F Street, NE MS 3040 Washington, DC 20549 To whom it may concern: The NYSE American certifies its approval for listing and registration of the Common Stock, no par value, of PINEAPPLE FINANCIAL IN

October 10, 2023 CORRESP

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.

October 10, 2023 CORRESP

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.

September 28, 2023 S-1/A

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.

September 28, 2023 CORRESP

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,

September 26, 2023 LETTER

LETTER

United States securities and exchange commission logo September 25, 2023 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc.

September 15, 2023 S-1/A

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.

September 15, 2023 EX-FILING FEES

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

July 6, 2023 CORRESP

VIA EDGAR

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

July 6, 2023 CORRESP

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.

July 6, 2023 CORRESP

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.

July 6, 2023 CORRESP

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.

July 6, 2023 8-A12B

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 5, 2023 CORRESP

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

July 5, 2023 S-1/A

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.

July 3, 2023 CORRESP

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

June 21, 2023 EX-99.3

Nominating and Corporate Governance Committee Charter

Exhibit 99.3

June 21, 2023 S-1/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.

June 21, 2023 EX-99.1

Audit Committee Charter

Exhibit 99.1

June 21, 2023 EX-14.1

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

June 21, 2023 EX-99.2

Compensation Committee Charter

Exhibit 99.2

May 16, 2023 EX-10.4

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

May 16, 2023 EX-10.2

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

Exhibit 10.2

May 16, 2023 EX-1.1

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,

May 16, 2023 EX-10.3

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

May 16, 2023 S-1/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.

May 16, 2023 EX-21.1

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%

May 16, 2023 EX-3.2

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

May 16, 2023 EX-3.1

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

May 16, 2023 EX-10.1

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

January 4, 2023 CORRESP

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

January 4, 2023 EX-10.4

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

January 4, 2023 EX-10.2

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

Exhibit 10.2

January 4, 2023 EX-21.1

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%

January 4, 2023 EX-10.3

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

January 4, 2023 S-1/A

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.

January 4, 2023 EX-1.1

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

December 13, 2022 LETTER

LETTER

United States securities and exchange commission logo December 13, 2022 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc.

December 1, 2022 S-1

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.

December 1, 2022 CORRESP

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,

December 1, 2022 EX-FILING FEES

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.

October 26, 2022 LETTER

LETTER

United States securities and exchange commission logo October 26, 2022 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc.

October 12, 2022 DRS/A

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

October 12, 2022 DRSLTR

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

September 28, 2022 LETTER

LETTER

United States securities and exchange commission logo September 28, 2022 Shubha Dasgupta Chief Executive Officer Pineapple Financial Inc.

September 1, 2022 DRS

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

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