# EDGAR Filing Document

**Accession Number:** 0001938109
**File Stem:** 0001493152-25-021901
**Filing Date:** 2025-11
**Character Count:** 22144
**Document Hash:** 4fea644734776994395a6b194e3881d9
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001493152-25-021901.hdr.sgml**: 20251112

**ACCESSION NUMBER**: 0001493152-25-021901

**CONFORMED SUBMISSION TYPE**: 8-K

**PUBLIC DOCUMENT COUNT**: 14

**CONFORMED PERIOD OF REPORT**: 20251107

**ITEM INFORMATION**: Entry into a Material Definitive Agreement

**ITEM INFORMATION**: Financial Statements and Exhibits

**FILED AS OF DATE**: 20251112

**DATE AS OF CHANGE**: 20251112

**FILER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** Pineapple Financial Inc.
- **CENTRAL INDEX KEY:** 0001938109
- **STANDARD INDUSTRIAL CLASSIFICATION:** FINANCE SERVICES [6199]
- **ORGANIZATION NAME:** 02 Finance
- **EIN:** 000000000
- **STATE OF INCORPORATION:** A1

**FILING VALUES:**
- **FORM TYPE:** 8-K
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-41738
- **FILM NUMBER:** 251472636

**BUSINESS ADDRESS:**
- **ADDRESS IS A NON US LOCATION:** YES
- **STREET 1:** 111 GORDON BAKER ROAD, SUITE 200
- **CITY:** NORTH YORK
- **PROVINCE COUNTRY:** A1
- **ZIP:** M2H3R1
- **BUSINESS PHONE:** 416-371-0835

**MAIL ADDRESS:**
- **ADDRESS IS A NON US LOCATION:** YES
- **STREET 1:** 111 GORDON BAKER ROAD, SUITE 200
- **CITY:** NORTH YORK
- **PROVINCE COUNTRY:** A1
- **ZIP:** M2H3R1

?xml version='1.0' encoding='ASCII'?

**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** |
| (State or other jurisdiction | (Commission | (IRS Employer |
| of incorporation) | File Number) | Identification No.) |

---

**Unit 200, 111 Gordon Baker Road**

**North York, Ontario M2H 3R1**

(Address of principal executive offices) (Zip Code)

**(416) 669-2046**

(Registrant's telephone number, including area code)

**Not Applicable**

(Former name or former address, if changed since last report)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (<u>see</u> General Instruction A.2. below):

☐ Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐ Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

☐ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐ Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

---

| | | |
|:---|:---|:---|
| **Title of each class** | **Trading Symbol(s)** | **Name of each exchange on which registered** |
| Common Shares, no par value | PAPL | NYSE American |

---

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§ 240.12b-2 of this chapter).

Emerging growth ☒

If an emerging growth company, indicate by check mart if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

**Item 1.01 Entry into a Material Definitive Agreement.**

***Third Amendment to Securities Purchase Agreement***

As previously disclosed, on September 2, 2025, Pineapple Financial Inc. (the "Company") entered into a securities purchase agreement, as amended on September 4, 2025 (the "Securities Purchase Agreement"), with certain accredited investors (the "Purchasers") pursuant to which the Company agreed to sell and issue to the Purchasers in a private placement offering subscription receipts (the "Subscription Receipts") of the Company at an offering price of $3.80 per Subscription Receipt, with respect to certain purchasers, and $4.16 per Subscription Receipt with respect to certain purchasers.

On November 7, 2025, the Company and the Purchasers of at least 50.1% in interest of the Subscription Receipts, entered into a third amendment to the Securities Purchase Agreement (the "Third SPA Amendment"). Pursuant to the Third SPA Amendment, the parties agreed that (i) the Company shall prepare, and shall file with the Securities and Exchange Commission (the "Commission") no later than December 5, 2025, the Registration Statement (as defined in the Securities Purchase Agreement), and (ii) cause the Registration Statement to be declared effective by the Commission as soon as possible and not later than the Escrow Deadline (as defined in the Purchase Agreement, as amended from time to time).

***First Amendment to the Registration Rights Agreement***

As previously disclosed, on September 2, 2025, the Company entered into a Registration Rights Agreement (the "Registration Rights Agreement"), pursuant to which the Company agreed to file a registration statement covering the resale of all Registrable Securities (as defined in the Registration Rights Agreement).

On November 7, 2025, the Company and the holders of a majority of the then outstanding Registrable Securities, entered into a first amendment to the Registration Rights Agreement (the "First RRA Amendment"). Pursuant to the First RRA Amendment, the parties agreed that (i) the Company shall prepare, and shall file with the Commission no later than December 5, 2025, the Registration Statement (as defined in the Securities Purchase Agreement), and (ii) cause the Registration Statement to be declared effective by the Commission as soon as possible and not later than the Escrow Deadline (as defined in the Purchase Agreement, as amended from time to time).

The foregoing summaries of the Third SPA Amendment and First RRA Amendment do not purport to be complete and are qualified in their entirety by reference to the complete text of the agreements, which are attached hereto as Exhibit 10.1 and Exhibit 10.2 to this Current Report on Form 8-K and are hereby incorporated by reference herein.

**Item 9.01 Financial Statements and Exhibits**

(a) Exhibits

---

| | |
|:---|:---|
| **Number** | **Description** |
| 10.1 | [Third Amendment to Securities Purchase Agreement, dated as of November 7, 2025](ex10-1.htm) |
| 10.2 | [First Amendment to Registration Rights Agreement, dated as of November 7, 2025](ex10-2.htm) |
| 104 | Cover Page Interactive Data File (embedded within the Inline XBRL document) |

---

**SIGNATURE**

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

Date: November 12, 2025

---

| | |
|:---|:---|
| **PINEAPPLE FINANCIAL INC.** | **PINEAPPLE FINANCIAL INC.** |
| By: | */s/ Shubha Dasgupta* |
|  | Shubha Dasgupta |
|  | Chief Executive Officer |

---

## Exhibit 10.1

**Exhibit 10.1**

**THIRD AMENDMENT TO**

**SECURITIES PURCHASE AGREEMENT**

This Third Amendment to Securities Purchase Agreement (this "<u>Third Amendment</u>") 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 "<u>Company</u>**"**) and each purchaser (each, including its successors and assigns, a "<u>Purchaser</u>" and collectively, the "<u>Purchasers</u>", and together with the Company, the "<u>Parties</u>") identified on the signature pages to that certain Securities Purchase Agreement, dated as of September 2, 2025, as amended on September 4, 2025, and November 3, 2025 (the "<u>Purchase Agreement</u>"). Capitalized terms used herein but not otherwise defined herein shall have the respective meanings assigned to such terms in the Purchase Agreement.

**<u>RECITALS</u>:**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;A. **WHEREAS**, the Company and the Purchasers entered into the Purchase Agreement, which sets forth the Parties' rights and obligations with respect to the transactions contemplated thereby;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;B. **WHEREAS**, in due consideration of the promises that the Parties have made to each other in the Purchase Agreement and therewith, the Parties desire to amend the Purchase Agreement in the manner set forth herein;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;C. **WHEREAS**, Section 5.5 of the Purchase Agreement provides that the Purchase Agreement may be amended in a written instrument signed by the Company and the Purchasers of at least 50.1% in interest of the Subscription Receipts, and the Injective Foundation, for as long as Injective Foundation is a holder of the Subscription Receipts (the "<u>Requisite Consent</u>");

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;D. **WHEREAS**, the Purchasers identified on the signature pages hereto constitute the Requisite Consent; and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;E. **WHEREAS**, the Parties intend that this Third Amendment shall be binding upon and inure to the benefit of each of the Parties and their respective successors and permitted assigns.

**NOW, THEREFORE**, in consideration of the mutual covenants and agreements hereinafter set forth and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the Parties agree as follows:

**ARTICLE I<u> </u>**

**<u>AMENDMENTS</u>**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1.1 Section 2.5 in the Purchase Agreement is hereby amended and restated in its entirety, and replaced with the following:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2.5 <u>Registration Statement Filing</u>. The Company shall (i) prepare, as soon as reasonably possible following the Closing Date, and shall file with the Commission no later than December 5, 2025, the Registration Statement (on Form S-1 or other appropriate registration statement form reasonably acceptable to the Purchasers) under the Securities Act, at the sole expense of the Company, in respect of the Purchasers, so as to permit the resale of the Shares, the Pre-Funded Warrants and the Pre-Funded Warrant Shares in the United States under the Securities Act; and (ii) cause the Registration Statement to be declared effective by the Commission as soon as possible and not later than the Escrow Deadline (as defined in the Purchase Agreement, as amended from time to time). The Company will notify the Placement Agent immediately following effectiveness of the Registration Statement. The Registration Statement shall cover the resale of 100% of the Shares, Pre-Funded Warrants and Pre-Funded Warrant Shares (including such indeterminate number of Common Shares resulting from stock splits, stock dividends or similar transactions), for an offering to be made on a continuous basis pursuant to Rule 415 (as promulgated by the Commission pursuant to the Securities Act, as such rule may be amended from time to time, or any similar rule or regulation hereafter adopted by the Commission having substantially the same purpose and effect as such rule). The Securities registered for resale pursuant to the Registration Statement shall not be subject to resale restrictions under Canadian Securities Laws, provided the distribution of the Securities will not take place prior to the Effective Date and the Securities will be distributed under the Registration Statement.

**ARTICLE II<u> </u>**

**<u>MISCELLANEOUS</u>**

**<u> </u>**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2.1 <u>No other Amendments</u>. Except as expressly amended hereby, the terms and conditions of the Purchase Agreement shall continue in full force and effect.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2.2 <u>Governing Law</u>. This Third Amendment shall be governed by and construed in accordance with the laws of the State of New York.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2.3 <u>Miscellaneous</u>. This Third Amendment may be executed in counterparts, each of which shall be deemed an original, but all of which together shall constitute one and the same instrument.

***[The remainder of this page is intentionally left blank.]***

 ****

 ****

**IN WITNESS WHEREOF**, the Parties have caused this Third Amendment to be signed by their respective officers thereunto duly authorized, all as of the date first written above.

---

| | |
|:---|:---|
| **COMPANY:** | **COMPANY:** |
| **PINEAPPLE FINANCIAL INC.** | **PINEAPPLE FINANCIAL INC.** |
| By: |  |
| Name: | Shubha Dasgupta |
| Title: | Chief Executive Officer |

---

[Signature Page to Third Amendment to Securities Purchase Agreement]

---

| |
|:---|
| **PURCHASER:** |
| By: |
| Name: |
| Title: |

---

## Exhibit 10.2

**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 "**Investor**" and collectively, the "**Investors**", and together with the Company, the "**Parties**") identified on the signature pages to that certain Registration Rights Agreement, dated as of September 2, 2025 (the "**Registration Rights Agreement**"). Capitalized terms used herein and not otherwise defined herein shall have the respective meanings set forth in the Registration Rights Agreement.

**<u>RECITALS</u>:**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;A. **WHEREAS**, the Company entered into a securities purchase agreement dated as of September 2, 2025, as amended, with certain accredited investors pursuant to which the Company agreed to sell and issue subscription receipts of the Company at an offering price of $3.80 per subscription receipt, with respect to certain purchasers, and $4.16 per subscription receipt with respect to certain purchasers (the "**Securities Purchase Agreement**");

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;B. **WHEREAS,** in connection with entering into the Securities Purchase Agreement, the Company and the Investors entered into a Registration Rights Agreement, pursuant to which the Company agreed to file a registration statement covering the resale of all Registrable Securities;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;C. **WHEREAS**, in due consideration of the promises that the Parties have made to each other in the Registration Rights Agreement and therewith, the Parties desire to amend the Registration Rights Agreement in the manner set forth herein;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;D. **WHEREAS**, Section 9 of the Registration Rights Agreement provides that the Registration Rights Agreement may be amended in a written instrument signed by (i) the Company and (ii) the holders of a majority of the then outstanding Registrable Securities (the "**Requisite Consent**");

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;D. **WHEREAS**, the Investors identified on the signature pages hereto constitute the Requisite Consent; and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;E. **WHEREAS**, the Parties intend that this First Amendment shall be binding upon and inure to the benefit of each of the Parties and their respective successors and permitted assigns.

**NOW, THEREFORE**, in consideration of the mutual covenants and agreements hereinafter set forth and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the Parties agree as follows:

**ARTICLE I**

**<u>AMENDMENTS</u>**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1.1 Section 2(a) in the Registration Rights Agreement is hereby amended and restated in its entirety, and replaced with the following:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**2.** **REGISTRATION.** 

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) <u>Mandatory Registration</u>. The Company shall prepare, as promptly as reasonably practicable after the Closing Date, and in any event no later than December 5, 2025 (the "**Filing Deadline**"), shall file with the SEC an initial Registration Statement (the "**Initial Registration Statement**") covering the resale of all Registrable Securities. Before filing the Registration Statement, the Company shall furnish to the Investors a copy of the Registration Statement. The Investors and their counsel shall have at least five (5) Business Days prior to the anticipated filing date of a Registration Statement to review and comment upon such Registration Statement and any amendment or supplement to such Registration Statement and any related prospectus, prior to its filing with the SEC, provided that such notice and prior review by the Investors and their counsel shall not be required in connection with any supplements or amendments related solely to the Company filing its regular Current Reports on Form 8-K. Subject to any SEC comments, such Registration Statement shall include the plan of distribution substantially in the form attached hereto as <u>Exhibit A</u>. The Company shall (a) use its reasonable best efforts to address in each such document prior to being so filed with the SEC such comments as the Investor or its counsel reasonably propose, and (b) not file any Registration Statement or related prospectus or any amendment or supplement thereto containing information regarding the Investor to which the Investor reasonably objects, unless such information is required to comply with any applicable law or regulation. The Investors shall promptly furnish all information reasonably requested by the Company and as shall be reasonably required in connection with any registration referred to in this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1.2 Section 2(b) in the Registration Rights Agreement is hereby amended and restated in its entirety, and replaced with the following:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) <u>Effectiveness.</u> The Company shall cause the Initial Registration Statement and any amendment declared effective by the SEC at the earliest possible date but no later than the Escrow Deadline (as defined in the Purchase Agreement, as may be amended from time to time). The Company shall notify the Investor by e-mail as promptly as practicable, and in any event, within 24 hours, after the Registration Statement is declared effective or is supplemented and shall provide the Investor with copies of any related prospectus to be used in connection with the sale or other disposition of the securities covered thereby. The Company shall use its best efforts to keep the Initial Registration Statement continuously effective pursuant to Rule 415 promulgated under the Securities Act and available for the resale by the Investors of all of the Registrable Securities covered thereby at all times until the earliest to occur of the following events: (i) the date on which the Investors shall have resold all the Registrable Securities covered thereby; and (ii) the date on which the Registrable Securities may be resold by the Investors without registration and without regard to any volume or manner- of-sale limitations by reason of Rule 144, without the requirement for the Company to be in compliance with the current public information requirement under Rule 144 under the Securities Act or any other rule of similar effect (the "**Registration Period**"). The Initial Registration Statement (including any amendments or supplements thereto and prospectuses contained therein) shall not contain any untrue statement of a material fact or omit to state a material fact required to be stated therein, or necessary to make the statements therein, in light of the circumstances in which they were made, not misleading.

**ARTICLE II**

**<u>MISCELLANEOUS</u>**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2.1 <u>No other Amendments</u>. Except as expressly amended hereby, the terms and conditions of the Registration Rights Agreement shall continue in full force and effect.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2.2 <u>Governing Law</u>. This First Amendment shall be governed by and construed in accordance with the laws of the State of New York.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2.3 <u>Miscellaneous</u>. This First Amendment may be executed in counterparts, each of which shall be deemed an original, but all of which together shall constitute one and the same instrument.

**[The remainder of this page is intentionally left blank.]**

 ****

**IN WITNESS WHEREOF**, the Parties have caused this First Amendment to Registration Rights Agreement to be signed by their respective officers thereunto duly authorized, all as of the date first written above.

---

| | |
|:---|:---|
| **COMPANY:** | **COMPANY:** |
| **PINEAPPLE FINANCIAL INC.** | **PINEAPPLE FINANCIAL INC.** |
| By: |  |
| Name: | Shubha Dasgupta |
| Title: | Chief Executive Officer |

---

[Signature Page to First Amendment to Registration Rights Agreement]

**IN WITNESS WHEREOF,** the parties have caused this First Amendment to Registration Rights Agreement to be duly executed as of date first written above.

---

| |
|:---|
| **INVESTOR:** |
| By: |
| Name: |
| Title: |

---