# EDGAR Filing Document

**Accession Number:** 0001938109
**File Stem:** 0001493152-25-026845
**Filing Date:** 2025-12
**Character Count:** 31927
**Document Hash:** dc55ea69d2cd3c17d95385fcb5af4a67
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001493152-25-026845.hdr.sgml**: 20251209

**ACCESSION NUMBER**: 0001493152-25-026845

**CONFORMED SUBMISSION TYPE**: 8-K

**PUBLIC DOCUMENT COUNT**: 16

**CONFORMED PERIOD OF REPORT**: 20251203

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

**ITEM INFORMATION**: Financial Statements and Exhibits

**FILED AS OF DATE**: 20251209

**DATE AS OF CHANGE**: 20251209

**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:** 251559109

**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): December 3, 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.**

***Fourth 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, November 3, 2025, and November 7, 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. The Subscription Receipts are governed by the terms of that certain subscription receipt agreement, dated September 4, 2025 (the "Subscription Receipt Agreement").

On December 3, 2025, the Company and the Purchasers of at least 50.1% in interest of the Subscription Receipts, entered into a fourth amendment to the Securities Purchase Agreement (the "Fourth SPA Amendment"). Pursuant to the Fourth SPA Amendment, the parties agreed to amend the Securities Purchase Agreement in order to (i) amend and restate the Escrow Deadline (as defined therein) in the Securities Purchase Agreement to one hundred twenty (120) days from the Closing Date, subject to further extension as set forth in the Fourth SPA Amendment, (ii) provide that the Company shall, immediately prior to the Escrow Release Date (as defined in the Subscription Receipt Agreement), appoint to the Board of Directors of the Company, one additional individual nominated by the Injective Foundation, and (iii) provide that the Company shall, no later than the Escrow Release Date (as defined in the Subscription Receipt Agreement), form the Special Advisory Committee of the Board of Directors of the Company consisting of three directors, including the individual appointed to the Board of Directors nominated by the Injective Foundation (the "Committee"). The Committee shall oversee the Company's digital asset treasury strategy and the implementation of the Company's treasury reserve policy in connection therewith. The Committee shall be authorized to engage such independent advisors (including, without limitation, legal, financial and compliance advisors) as the Committee deems necessary to carry out its responsibilities, including the engagement of up to three individuals identified by the Injective Foundation as strategic advisors to the Committee.

***Fifth Amendment to Securities Purchase Agreement***

On December 5, 2025, the Company and the Purchasers of at least 50.1% in interest of the Subscription Receipts, entered into a fifth amendment to the Securities Purchase Agreement (the "Fifth SPA Amendment"). Pursuant to the Fifth 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 15, 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).

***Second Amendment to the Registration Rights Agreement***

As previously disclosed, on September 2, 2025, the Company entered into a Registration Rights Agreement, as amended on November 7, 2025 (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 December 5, 2025, the Company and the holders of a majority of the then outstanding Registrable Securities, entered into a second amendment to the Registration Rights Agreement (the "Second RRA Amendment"). Pursuant to the Second RRA Amendment, the parties agreed that (i) the Company shall prepare, and shall file with the Commission no later than December 15, 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 Fourth SPA Amendment, the Fifth SPA Amendment, and Second 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 Exhibits 10.1, Exhibit 10.2, and Exhibit 10.3 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 | [Fourth Amendment to Securities Purchase Agreement, dated as of December 3, 2025](ex10-1.htm) |
| 10.2 | [Fifth Amendment to Securities Purchase Agreement, dated as of December 5, 2025](ex10-2.htm) |
| 10.3 | [Second Amendment to Registration Rights Agreement, dated as of December 5, 2025](ex10-3.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: December 9, 2025

---

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

---

## Exhibit 10.1

**Exhibit 10.1**

**FOURTH AMENDMENT**

**TO**

**SECURITIES PURCHASE AGREEMENT**

This Fourth Amendment to Securities Purchase Agreement (this "<u>Fourth Amendment</u>") 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 "<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, November 3, 2025, and November 7, 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 (as defined below).

**<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 Fourth 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 The definition of "Escrow Deadline" in the Purchase Agreement is hereby amended and restated in its entirety, and replaced with the following:

"<u>Escrow Deadline</u>" means one hundred twenty (120) days from the Closing Date, subject (i) to an automatic extension to an aggregate of one hundred fifty (150) days from the Closing Date in the event that the Commission notifies the Company that it will review the Registration Statement, and (ii) such further extension(s) to be agreed to in writing by the holders of 50.1% or more of the Subscription Amounts, including Injective Foundation, acting reasonably, in accordance with the Subscription Receipt Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1.2 Section 4.21 of 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;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;4.21 <u>Appointment of Director</u>. The Company shall take all necessary action such that, immediately prior to the Escrow Release Date, one additional individual nominated by the Injective Foundation, with knowledge and expertise in the crypto industry, is appointed to the Board of Directors of the Company, subject to meeting the requirements of the Stock Exchange. At the time of such appointment, the Company shall (A) maintain in effect a commercially reasonable directors' and officers' liability insurance policy with a term extending at least one calendar quarter beyond the date of such nominee's appointment, and (B) concurrently reassess and determine the independence of each independent director then serving on the Board of Directors of the Company for purposes of ensuring compliance with the Stock Exchange governance requirements.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1.3 The Purchase Agreement is hereby amended to add a new Section 4.22 thereto, which shall read in its entirety as follows:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;4.22 <u>Formation of Special Advisory Committee</u>. The Company shall take all necessary action such that, no later than the Escrow Release Date, the Board of Directors shall form the Special Advisory Committee of the Board of Directors of the Company (the "<u>Committee</u>"). The Committee shall be composed of three directors, including the individual appointed to the Board of Directors pursuant to Section 4.21 hereof, which individual shall serve as the initial chair of the Committee. Concurrently, the Board of Directors shall adopt a written Committee charter that will outline the Committee's duties and responsibilities in carrying out the Company's digital asset treasury strategy, as well as setting up the Committee's governance structure. The Committee shall have the authority to oversee the Company's digital asset treasury strategy, including without limitation, the adoption and implementation of the treasury reserve policy that shall be adopted in accordance with Section 4.19 of the Purchase Agreement, as well as the operational and strategic matters relating to the Company's digital asset treasury operations. The Committee shall be authorized to engage, retain, compensate and terminate, at the Company's expense, such independent advisors (including, without limitation, legal, financial and compliance advisors) as the Committee deems necessary or appropriate to carry out its responsibilities, and to approve the fees and retention terms of such advisors. The Committee shall further be authorized to coordinate directly with the Company's officers, appropriate internal teams and external service providers, and access and utilize the resources of the Company, to oversee the execution of the Company's digital asset treasury strategy and adopt and implement the Company's treasury reserve policy.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1.4 The Purchase Agreement is hereby amended to add a new Section 4.23 thereto, which shall read in its entirety as follows:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;4.23 <u>Committee Advisors</u>. The Company shall take all necessary action such that, no later than the Escrow Release Date, the Committee shall be authorized and able to engage 3 individuals identified by Injective Foundation (collectively, the "<u>Advisors</u>") as strategic advisors to the Committee. The Committee shall enter into advisory agreements with each of the Advisors providing, among other terms: (i) that the Advisors will provide advice to the Committee and the Board relating to the digital asset treasury strategy and the drafting and implementation of the treasury reserve policy, and (ii) an initial term of one year, with provision for automatic renewal subject to customary exceptions.

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

**<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 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 Fourth 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 Fourth 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 Fourth 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 Fourth Amendment to Securities Purchase Agreement]

---

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

---

[Signature Page to Fourth Amendment to Securities Purchase Agreement]

---

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

---

[Signature Page to Fourth Amendment to Securities Purchase Agreement]

## Exhibit 10.2

**Exhibit 10.2**

**FIFTH AMENDMENT**

**TO**

**SECURITIES PURCHASE AGREEMENT**

This Fifth Amendment to Securities Purchase Agreement (this "<u>Fifth Amendment</u>") 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 "<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, November 3, 2025, November 7, 2025, and December 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 Fifth 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 15, 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>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 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 Fifth 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 Fifth 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 Fifth Amendment to be signed by their respective officers thereunto duly authorized, all as of the date first written above.

---

| |
|:---|
| **COMPANY:** |
| **PINEAPPLE FINANCIAL INC.** |
| By: |
| Name: |
| Title: |

---

[Signature Page to Fifth Amendment to Securities Purchase Agreement]

---

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

---

[Signature Page to Fifth Amendment to Securities Purchase Agreement]

## Exhibit 10.3

**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 "**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, as amended on November 7, 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 Second 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;&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 15, 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.

**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 Second 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 Second 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 Second Amendment to Registration Rights Agreement to be signed by their respective officers thereunto duly authorized, all as of the date first written above.

---

| |
|:---|
| **COMPANY:** |
| **PINEAPPLE FINANCIAL INC.** |
| By: |
| Name: |
| Title: |

---

[Signature Page to Second Amendment to Registration Rights Agreement]

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

---

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

---

*[Signature Page to Second Amendment to Registration Rights Agreement]*

 

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

---

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

---

*[Signature Page to Second Amendment to Registration Rights Agreement]*