Form 8-K

8-K — Pineapple Financial Inc.

Accession: 0001493152-26-018582

Filed: 2026-04-22

Period: 2026-04-22

CIK: 0001938109

SIC: 6199 (FINANCE SERVICES)

Item: Regulation FD Disclosure

Item: Other Events

Item: Financial Statements and Exhibits

Documents

8-K — form8-k.htm (Primary)

EX-99.1 (ex99-1.htm)

EX-99.2 (ex99-2.htm)

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2026-04-22

iso4217:USD

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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

Employer

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 (see 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 ☒

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

7.01. Regulation FD Disclosure

Repurchase Program

April 22, 2026, Pineapple Financial Inc. (the “Company”) issued a press release announcing that its Board of Directors has

approved an expansion of its previously announced share repurchase program, as described in greater detail in Item 8.01 of this Current

Report on Form 8-K. A copy of the press release is furnished hereto as Exhibit 99.1.

Presentation

connection with the share buyback, the Company delivered a presentation which provides key operating & financial metrics (the “Presentation”).

A copy of the Presentation is furnished hereto as Exhibit 99.2.

Item

8.01 Other Events.

April 22, 2026, the Company’s Board of Directors approved an expansion of its previously announced share repurchase

program, increasing the aggregate authorization from US$3,000,000 to up to US$15,000,000 of the Company’s outstanding common

shares. The shares may be repurchased from time to time in open market purchases and pursuant to safe harbors provided by Rule 10b-18

and Rule 10b5-1 under the Securities Exchange Act of 1934. The timing, manner, price and amount of any repurchases under the expanded

share repurchase program will be determined by the Company in its discretion. The stock repurchase program does not require the Company

to repurchase any specific number of shares, and may be modified, suspended or terminated at any time.

Item

9.01 Financial Statements and Exhibits

(a)

Exhibits

Number

Description

99.1

Press

Release dated April 22, 2026

99.2

Presentation

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:

April 22, 2026

PINEAPPLE

FINANCIAL INC.

By:

/s/

Shubha Dasgupta

Shubha

Dasgupta

Chief

Executive Officer

EX-99.1

Filename: ex99-1.htm · Sequence: 2

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 expansion of its previously announced share repurchase program, increasing the aggregate

authorization from US$3,000,000 to up to US$15,000,000 of Pineapple’s common shares.

The Company also announced that it intends to

commence repurchasing shares immediately under the previously approved US$3,000,000 authorization, subject to applicable securities laws

and the absence of material non-public information at the time of purchase.

The expanded authorization includes (i) the initial

US$3,000,000 to be executed under the existing program, and (ii) an additional up to US$12,000,000, which may be repurchased from time

to time, subject to further Board approval, satisfaction of applicable solvency requirements, and the Company’s financial condition,

liquidity position, and capital allocation priorities.

The timing and price of repurchases as well as

the actual number of shares repurchased under the expanded share purchase program will be at the discretion of the Company and

will depend on a variety of factors, including general market conditions, the stock price, regulatory requirements and limitations, trading

blackout periods, necessary corporate approvals, applicable corporate solvency requirements, corporate liquidity requirements

and priorities, and other factors.

About Pineapple Financial Inc.

Pineapple Financial Inc. is an award-winning fintech

and leading Canadian mortgage brokerage network, focusing on both the long-term success of agents and brokers as well as the overall experience

of homeowners. With hundreds of brokers within the network, Pineapple creates cutting-edge cloud-based tools and AI-driven systems to

enable its brokers to help Canadians realize their dream of owning a home. Pineapple is active within the community and is proud to sponsor

charities across Canada to improve the lives of fellow Canadians.

Safe Harbor Forward-Looking Statements

Certain statements in this announcement are forward-looking

statements. These forward-looking statements involve known and unknown risks and uncertainties. They are based on the Company’s current

expectations and projections about future events that the Company believes may affect its financial condition, results of operations,

business strategy and economic needs. Investors can identify these forward-looking statements by words or phrases such as “may,”

“will,” “expect,” “anticipate,” “aim,” “estimate,” “intend,” “plan,”

“believe,” “is/are likely to,” “potential,” “continue” or other similar expressions. The Company

undertakes no obligation to update or revise publicly any forward-looking statements to reflect subsequent occurring events or circumstances

or changes in its expectations that arise after the date hereof, except as may be required by law. These statements are subject to uncertainties

and risks including, but not limited to, the uncertainties related to market conditions, fluctuations in the market price of INJ and

any associated impairment charges that we may incur as a result of a decrease in the market price of INJ below the value at which INJ

is carried on our balance sheet; changes in the accounting treatment relating to our INJ holdings; the Company’s financial condition,

customer acceptance of our INJ treasury strategy, and other factors discussed in the “Risk Factors” section of the registration

statements, and periodic reports filed with the SEC. Although the Company believes that the expectations expressed in these forward-looking

statements are reasonable, it cannot assure that such expectations will be correct. The Company cautions investors that actual results

may differ materially from the anticipated results. It encourages investors to review other factors that may affect its future results

in the Company’s registration statement and other filings with the SEC. Additional factors are discussed in the Company’s filings with

the SEC, which are available for review at www.sec.gov.

Media Contact:

KCSA Strategic Communications

Kristin Cwalinski

pineapple@kcsa.com

Investor Relations:

KCSA Strategic Communications

Jack Perkins

pineapple@kcsa.com

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