Pineapple Financial Inc. Hosts Third Annual Charitable 3-on-3 Basketball Tournament to Benefit MLSE Foundation

Toronto, ON, March 12, 2024 – Pineapple Financial Inc. (NYSE American: PAPL), (“the Company or “Pineapple”), a tech-focused mortgage brokerage with an integrated network of partner brokerages and agents across Canada, today announced that it hosted its 3rd Annual 3-on-3 Basketball Tournament on Saturday, March 9, 2024 raising over $21,700 for the MLSE Foundation, the youth-focused charitable arm of Maple Leaf Sports & Entertainment Ltd..

All proceeds from the tournament went directly to the MLSE Foundation to support its charitable causes, including building sports facilities, providing equipment, and delivering empowering programs aimed at creating positive change in the lives of young people.

Over the past three years, Pineapple has now raised over $50,000 for the Foundation.

"We were thrilled to host this Tournament in support of the MLSE Foundation," said Christa Mitchell, Chief Strategy Officer at Pineapple Financial Inc. "We believe in the power of sport to bring communities together. By partnering with MLSE Foundation, we hope to contribute to their mission of positively impacting young people's lives in our community."

In raising the proceeds, Pineapple brought together hundreds of industry participants across Canada, including lenders, lawyers, realtors, brokers, appraisers, insurers, staff, and clients. Pineapple’s partners generously supported this event:  MLSE, MSLE Foundation, Community Trust, First National, EQ Bank, MCAP, Top Law Firm, Strive Capital, CMI Financial Group, VWR Capital Corp., Haventree Bank, MCAN Financial,  Glasslake Funding, Team You First, Indochino, The University of British Columbia, Bridgewater Bank, No Days Wasted, RMG Mortgages, RFA Mortgage, NPX, CMLS/AVEO, Ginkgo, Scotiabank, Home Trust, Canada Basketball, and Stockton & Bush, which assisted by sponsoring teams, donating items for door prizes and a silent auction, volunteering at the event, and supporting the participants.

“This event reflects our commitment to supporting communities across Canada,” added Ms. Mitchell. “Pineapple believes that together, we can make an impactful difference in the lives of underprivileged youth through the joy of sports. We are eager to continue collaborating with the MLSE Foundation to create lasting opportunities for the youth in our communities.”

“The MLSE Foundation has spent over a decade investing millions of dollars into youth and communities faced with barriers,” said Brett Fyfer, Campaign Manager at MLSE Foundation. “We are proud to partner with Pineapple Financial Inc. for the third year to raise funds and awareness to address systemic barriers preventing youth from reaching their potential.”

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About MLSE Foundation

MLSE Foundation is the charitable arm of Maple Leaf Sports & Entertainment Ltd. (MLSE). With a mission to improve the lives of youth through sport and recreation, MLSE Foundation focuses on providing outlets for underprivileged youth, establishing sustainable programs, and empowering individuals to reach their full potential. Learn more at www.mlsefoundation.org.

About Pineapple Financial:

Pineapple is an award-winning fintech and leading Canadian mortgage brokerage network,  focusing on the long-term success of agents and brokers and the overall experience of homeowners. With approximately 700 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.

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SOURCE: Pineapple Financial Inc. (NYSE American: PAPL)

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Certain statements in this announcement are forward-looking statements. These forward-looking statements involve known and unknown risks and uncertainties and 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 financial 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 and the completion of the initial public offering on the anticipated terms or at all, and other factors discussed in the “Risk Factors” section of the registration statement filed with the SEC. Although the Company believes that the expectations expressed in these forward-looking statements are reasonable, it cannot assure you that such expectations will turn out to be correct, and the Company cautions investors that actual results may differ materially from the anticipated results and 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:

For media inquiries, please get in touch with Dennis Welsh, Senior Director of Marketing, at Pineapple.

Email: dennis@gopineapple.com

Investor Relations Contact:

For investor relations inquiries, please get in touch with Scott Powell, Chief Executive Officer, at Skyline Corporate Communications Group, LLC

Email: scott@skylineccg.com

Phone: +1 (646) 893-5835