Approximately 554,581 Shares Repurchased and Retired to Date Under Expanded Buyback Authorization

Digital Asset Treasury Valued at Approximately $52.53 Million; Current mNAV Estimated at 0.82x

Toronto, Ontario--(Newsfile Corp. - May 20, 2026) - Pineapple Financial Inc. (NYSE American: PAPL) ("Pineapple" or "the Company"), a leading fintech platform, today provided an update regarding its previously announced share repurchase program. Following the launch of the Company's expanded authorization, Pineapple has begun retiring repurchased common shares and expects to retire additional shares on an ongoing basis as purchases are executed in the open market, in accordance with applicable securities laws.

To date, Pineapple has repurchased approximately 554,581 common shares of stock, representing approximately $657,060.29 of capital deployed. As previously announced, Pineapple's Board of Directors approved an expanded share repurchase authorization of up to $15 million, including an initial $3 million tranche currently being executed in the open market. The Company believes the authorization provides flexibility to continue opportunistically acquiring shares and balancing liquidity, while progressing operational growth initiatives and broader capital allocation priorities.

"Our share repurchase activity reflects the resounding confidence that management and our Board of Directors have in Pineapple's long-term strategy, balance sheet strength, and underlying intrinsic value," said Shubha Dasgupta, CEO and Co-Founder of Pineapple Financial. "While we have only utilized a small portion of authorized capacity to date, we believe the current market valuation does not fully reflect the strength of our mortgage platform, the scale of our digital asset treasury, or the long-term value creation opportunity across our technology and tokenization strategy. We remain committed to disciplined capital allocation and believe that continuing to retire shares at current levels represents an attractive use of capital for shareholders."

As of the close of business on May 19, 2026, Pineapple's Digital Asset Treasury had an aggregate value of approximately $52.53, comprised of 7.56 million Injective ("INJ") tokens, over $10 million stablecoin holdings, and approximately $10 million in cash reserves. The Company's Digital Asset Treasury strategy continues to include a diversified mix of digital assets, stablecoin positions, yield-generating strategies, and other treasury-related exposures designed to enhance balance sheet productivity and long-term shareholder value.

Management does not believe the Company's current market valuation fully reflects the value of its underlying treasury assets, treasury-related income generation capabilities, and broader DAT strategy. Based on the Company's most recent internal calculations, Pineapple's current mNAV is approximately 0.82x, which management believes reflects an ongoing disconnect between the Company's public market valuation and the value of its underlying asset base, including its operating platform, cash position, and digital asset treasury consisting of Injective ("INJ") tokens and stablecoin holdings. With the Company continuing to trade below 1.0x mNAV, management believes opportunistic share repurchases may represent an attractive and accretive capital allocation opportunity, particularly following Injective's recent appreciation of nearly 100% over recent weeks. The Company remains focused on maintaining prudent liquidity and risk management practices while continuing to optimize long-term treasury performance. The Company expects to provide additional updates regarding repurchase activity periodically via future public disclosures and applicable regulatory filings.

About Pineapple Financial Inc.
Pineapple Financial Inc. (NYSE American: PAPL) is a publicly traded company with a digital asset treasury strategy focused on accumulating INJ tokens through disciplined open-market purchases. The Company is committed to delivering shareholder value through strategic capital allocation in the dynamic digital asset landscape.

In addition to its digital asset treasury, Pineapple 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.

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