Pineapple Financial Inc.

General

Pineapple Financial is a Canadian mortgage technology and brokerage company. We provide mortgage brokerage services and technology solutions to Canadian mortgage agents, brokers, sub-brokers, brokerages and consumers. Through data-driven systems and cloud-based tools, we believe we offer competitive advantages in the Canadian mortgage industry relative to traditional broker arrangements.

We also provide back-office and pre-underwriting support services (together, the “Brokerage Services”) to Canadian mortgage brokerages (the “Brokerages”). In connection with the provision of the Brokerage Services, we employ and engage licensed mortgage brokers and agents (collectively, “Field Agents”). As of the date of this filing, we have 39 full-time employees. In addition, we enter into affiliation agreements with certain licensed mortgage brokers (“Affiliate Brokers” and, together with Field Agents and Brokerages, the “Users”) under which we jointly market mortgage brokerage and other financial services as affiliated entities. This “white-label” model allows Affiliate Brokers to offer mortgages under their own brand to their client base while operating on our platform and within our controls.

We offer Brokerage Services for both residential and commercial mortgage opportunities through our proprietary technology platform, Pineapple+ [and related tools, together, the “Platform”]. The Platform supports the mortgage life cycle from lead intake and pre-qualification through underwriting support, documentation, compliance, and funded-deal analytics.

Revenue Model

Our revenue model is diversified across platform subscriptions, pre-risk assessment services and lender partner commissions. Percentages below are approximate and subject to period-to-period variation.

1.Subscription services. Agents who use the Platform to manage the life cycle of a mortgage from initiation to funding pay subscription fees of $141.50 per month. This stream represents approximately 3% of total gross revenue.

2.Pre-risk assessment services. We charge a per-deal fee for pre-underwriting support and documentation preparation. For mortgages with a funded amount of $390,000 and over, the fee is $390 per deal. For mortgages under $390,000, the fee is $273 per deal. This stream represents approximately 1.3% of total gross revenue.

3.Lender partner service commissions. The balance of total gross revenue, approximately 95%, is derived from commissions and volume-based compensation from lender partners. Commission structures vary by rate, amount, promotional programs, bonus eligibility and funded volume. Our lender partners include banks, trust companies, mortgage finance companies and other financial institutions, including but not limited to; Bank of Nova Scotia (Scotiabank), Manulife Bank of Canada, Toronto-Dominion Bank, MCAP, First National Financial LP, Home Trust Company, Equitable Bank, Community Trust, Bank of Montreal (BMO) and Desjardins Mortgage Financing Services.

Geographic Footprint and Licensing

We currently operate in Canada, with active brokerage operations in Ontario, Newfoundland and Labrador, New Brunswick, Nova Scotia, British Columbia, Prince Edward Island, Manitoba and Alberta. We launched our first brokerage in Ontario in November 2016, opened our Alberta office on July 1, 2021, expanded into Newfoundland and Labrador, Nova Scotia, New Brunswick and Prince Edward Island on May 4, 2022, and opened our first British Columbia brokerage office in 2024. We have been approved by applicable provincial mortgage regulators to operate in the following provinces and territories: Alberta, British Columbia, New Brunswick, Newfoundland and Labrador, Northwest Territories, Nova Scotia, Nunavut, Prince Edward Island, Quebec and Yukon, and we are pursuing additional licensing in Saskatchewan.

Technology

Our Platform integrates lead routing, CRM, document collection, compliance workflows, lender connectivity and analytics. By centralizing workflow and data, we aim to improve agent productivity, reduce turnaround times and enhance compliance monitoring. The Platform is cloud-hosted with role-based access controls, audit trails and data security protocols that are designed to meet or exceed applicable regulatory expectations.

Digital Asset Treasury Strategy

In fiscal 2025, we established a digital asset treasury strategy (the “Treasury Strategy”) as a component of our corporate treasury and strategic partnership program. The Treasury Strategy permits the Company, subject to internal policies, board oversight and applicable law, to hold a capped allocation of liquid digital assets to support research and development, ecosystem partnerships and potential future integrations with our mortgage technology stack. As of the date of this filing, the Treasury Strategy is managed separately from brokerage operations. The Treasury Strategy is subject to strict custody, risk, accounting and compliance policies, including segregation of assets, volatility limits, impairment monitoring and disclosure controls.

On-Chain Mortgage Development

We are conducting research and development to explore the application of distributed ledger and smart-contract technologies to selected elements of the mortgage lifecycle (“On-Chain Mortgage Development”). Areas of exploration include, among others, identity and document attestations, collateral and lien data registries, payment and remittance workflows, servicing data integrity, and potential future pathways for asset issuance and investor reporting. These initiatives are currently in development and do not contribute material revenue. Any commercial deployment will require successful technical validation, market acceptance, appropriate regulatory permissions and the establishment of robust compliance, privacy and security controls. We may pursue pilot programs with ecosystem partners and service providers to evaluate feasibility and cost-benefit outcomes.

Compliance and Regulatory

Our brokerage activities are subject to provincial mortgage brokerage laws and regulations, consumer protection requirements, anti-money laundering and anti-terrorist financing obligations, privacy and data protection laws and related guidance. We maintain policies, procedures, training and supervision designed to promote compliance, including for third-party affiliates who operate on our Platform. Our Treasury Strategy and On-Chain Mortgage Development are subject to additional legal, accounting, tax and regulatory considerations. We evaluate these programs with external legal counsel and advisors and implement governance, risk and control frameworks that we believe are appropriate for their scope and scale.

MyPineapple

At the heart of our Brokerage Services is an innovative technology system, MyPineapple, that provides real time data management and reporting, lead generation opportunities, customer relationship management, deal processing, education and knowledge center, payroll, regulatory compliance, data analytics, document collection and storage, automated onboarding, lender access, back office support and direct underwriting support, all in one. MyPineapple offers network management capabilities for Users, including hundreds of qualified Field Agents, to create an efficient marketplace for the provision of mortgage lending and insurance industry services. MyPineapple integrates directly with Equifax, OneSpan, G Suite and Filogix and manages Users’ day-to-day business through automated triggers and tasks, ensuring nothing falls through the cracks. MyPineapple syncs up with Users’ calendar and emails, produces robust reporting, advanced analytics, and real-time notifications on marketing communications, and more. MyPineapple is a sophisticated and fundamental tool for revenue growth and relationship development. It plays a significant role in what we believe makes our Brokerage Services distinct and cutting-edge.

MyPineapple was created to address key issues within the mortgage brokerage industry. We built MyPineapple to create a long-term competitive advantage relative to traditional service providers, who have comparatively high-touch, labor intensive and costly operations. We believe that, through MyPineapple, we are able to deliver faster services and with fewer errors. Our MyPineapple platform is completely automated, simplifying the mortgage process while providing efficiencies to and alleviating pressure on Users’ staff in completing traditional administrative tasks, which in turn reduces the Users’ cost structure and results in increased profit margins and scalability. MyPineapple reduces manual processes through robust quality control mechanisms, logistics management capabilities, capacity planning tools and end-to-end transaction management. MyPineapple also includes a leading education technology platform, which enables Users to continuously stay informed and educated on what mortgage solutions and market conditions could impact Canadian consumers.

Our primary objectives and goals include, but are not limited to, the following:

● Grow our mortgage broker distribution channel to gain further market share and consumer adoption, including increasing organic (non-acquisition related) market share and to achieve growth on the number of mortgages funded annually;

● Become the go-to mortgage experience platform for mortgage agents, lenders and homebuyers;

● For Pineapple Insurance to provide an insurance option for all our mortgage approvals;

● To ensure that we are providing a well-rounded and custom-tailored approach to insurance solutions that may best suit the clients’ needs;

● To leverage the power of our growing database and brand recognition to open further insurance opportunity channel; and

Streamline the insurance approval and application process for mortgage clients using technology.

Services and Products Brokerage Services

The following is a detailed description of the Brokerages Services that we offer:

1. Mortgage Brokering: We employ and engage a number of licensed Field Agents who originate clients, provide mortgage consultation services, advise clients on the various mortgage products offered by financial institutions in Canada, offer clients access to rate information and mortgage options from a range of lenders, including major banks and lending institutions and assist clients in selecting the most appropriate and effective mortgage solution for their particular needs.

2. Technology: MyPineapple is a full spectrum, robust and comprehensive technology system, which allows Users to conduct their brokerage services more effectively and efficiently. Amongst other things, MyPineapple syncs up with Users’ calendar and emails, produces robust reporting, advanced analytics, and real-time notifications for email opens, and link clicks. MyPineapple also provides Users with cloud storage. We also provide marketing support to Users in order to systematically manage the marketing process, segmentation and client conversions. We ensure that all clients stay well informed with highly relevant information; it also increases the conversion ratios and engagement metric for its Users. This provides Users the ability to focus on higher probability clients and deliver a high level of value and service while the system manages the relationship with others.

3. Back Office Support Services: Through MyPineapple, we offer our Users back office support services, including digital and automated onboarding and set up, loan packaging and processing, digital document collection and client portals, loan maintenance activities, payroll, lender communication, reporting requirements for regulators and business management, cloud services, expense collections, document preparation, compliance, training, administration and marketing.

4. Pre-Underwriting Support: Technology enabled and together with back-office support, we offer our Users pre-underwriting support services that establish appropriate qualifying processes in a mortgage application, providing borrowers a digital environment ensuring mortgage agents has the necessary data and providing borrowers with an instant pre-qualification. We use our diverse exposure to the mortgage industry to save Users from spending valuable resources on mortgage applications that have fewer chances of reaching approval. In particular, we offer our Users the following pre-underwriting services, aimed at speeding up the underwriting process and helping mortgage lenders make accurate decisions:

● Credit Review: We verify all information that is supplied by the client in vital loan documents and other personal information. Thereafter, we meticulously review client credit records and tax return documents to ensure the client has the required financial stability to make monthly payments for the mortgage. We follow checklist-based system to ensure that all the critical aspects pertaining to underwriting are covered.

● Data Validation: Our pre-underwriting support services include recording and digitizing our findings in the data validation process. By digitizing these vital information sets about the client, we are able to establish the accuracy and speed needed to expedite the underwriting process.

● Fraud Analysis and Compliance: We pride ourselves in diligently checking for identity fraud and ensuring that applications are compliant and contain complete information. Our mortgage experts have the experience and acumen to spot missing or mala fide information. This obviates the need for the underwriter to send client files back for incomplete information and thereby speeds up the underwriting process. Our fraud analysis encompasses all aspects of the client file review process including running third-party reports. This ensures the underwriter has to focus only on decision-making.

● Appraisal Ordering and Review: We take charge of title ordering and dispatching verified property information to the appraiser to boost the turnaround times of the appraisal process. Once the appraisal is over, we carefully review the appraisal report to ensure that the process has been completed in a fair and error-free manner.

● Data Analytics: Through MyPineapple, we are able to use data to analyze customer benefit opportunities as they become available. In particular, MyPineapple allows us to utilize the data that has been acquired through the mortgage approval process along with real time real estate and credit data to thereby reduce costs and overall debt process timelines.

Pineapple Insurance Inc. is a wholly owned subsidiary of Pineapple Financial Inc. This entity is to serve the insurance needs of our brand mortgage brokers and agents across Canada. Pineapple Insurance is to act as a Managing General Agent (MGA) supported by Industrial Alliance. This entity will create both a revenue channel and retention strategy for borrowers that live within our database. This will also allow a growth opportunity and an overall holistic financial services opportunity for us. We are currently in the early stages of development of Pineapple Insurance Inc. Operational infrastructure and a budget has been prepared alongside technology modifications to our MyPineapple system in order to manage the delivery of this product. We have also created a sales and marketing plan alongside assets and materials, which will be used for initial launch. Our next steps are staffing and human capital requirements in order to execute on the business plan and goals of developing Pineapple Insurance.

Pineapple Insurance provides the following services:

● We will complete a needs analysis on each client to ensure the most suitable product to meet both their needs and their goals. In our product suite, we will offer term life insurance which will provide a low-cost coverage at a fixed rate of payments for a limited period of time for the life of the mortgage. The goal of this product is to ensure that in the event of the insurer’s untimely death with their term policy their beneficiaries will be covered in the amount of the policy during the life of the term. No insurance will be paid to the beneficiary should the insured pass away after the end of the term or if the insured did not make the required payments.

● Whole Life Insurance is a life insurance policy which is guaranteed to remain in force for the insured’s entire lifetime, provided required premiums are paid, or to the maturity date. In addition to paying a death benefit, whole life insurance also contains a savings component in which cash value may accumulate on a tax-advantaged basis. The policies can be leveraged as collateral or an asset with our lenders through the Company.

● For both our personal and our business clients, we offer permanent life insurance policies, which offer a death benefit and cash value. The death benefit is money that is paid to your beneficiaries when you pass away. Cash value is a separate savings component that you may be able to access while you are still alive. Permanent insurance can help cover the business owner for their entire life. And unlike term insurance, it includes the potential for a cash accumulation fund. Investments in the fund are tax-preferred, including at death when the tax-free death benefit is paid out to a named beneficiary. An additional benefit of permanent life insurance is that allocating funds in a corporation away from taxable investments to a permanent life insurance policy can help reduce overall annual taxable investment income. Permanent life insurance lasts from the time you buy a policy to the time you pass away, as long as you pay the required premiums. The policies can be leveraged as collateral or an asset with our lenders through the Company.

● Critical Illness Insurance provides additional coverage for medical emergencies like heart attacks, strokes, or cancer. Because these emergencies or illnesses often incur greater-than-average medical costs, these policies pay out cash to help cover those overruns where traditional health insurance may fall short and help cover living expenses while the client recovers. These policies come at a relatively low cost. However, the instances that they will cover are generally limited to a few illnesses or emergencies. The key element is to ensure that the mortgagor does not fall behind in their mortgage payments.

● Credit Insurance is a type of life insurance that can cover the remaining amount of your loan in the event of your death. Your insurance company will use the death benefit to pay down or pay off the remaining balance on the loan, up to a maximum amount outlined in the certificate of insurance. The money from your death benefit will go to your creditor. The money will not go to your family or beneficiaries.

We offer a wide range of investment options to suit clients risk tolerance and investment preferences. A financial advisor will review and assess the needs of each client to determine the short- and long-term goals for financial success. Such options may include segregated funds or mutual funds for registered (registered education savings plans (RESPs), registered retirement savings plans (RRSPs), tax-free savings accounts (TFSAs), etc.) and non-registered accounts. A segregated fund, or seg fund, is a type of investment fund administered by Canadian insurance companies in the form of individual, variable life insurance contracts offering certain guarantees to the policyholder such as reimbursement of capital upon death and mutual funds. As a regulatory requirement, all Canadian mortgage approvals being presented by the mortgage broker channel must include the option for a client to consider an insurance option in an effort to protect the liability in the case of death or disability. Pineapple Insurance Inc. will be presenting this insurance option for a client to accept or not via the products that we have available. This will be presented to all mortgage approvals being offered via our parent company, Pineapple Financial Inc.

As a complementary service to our parent company, Pineapple Financial Inc., this insurance subsidiary was created to easily serve the needs of the homeowners whose mortgages originate with us. With any mortgage product in Canada, an insurance component is a requirement, hence the diversification and business development into insurance.

Our insurance services identified above currently are provided by a third-party insurance company, Industrial Alliance Inc., with whom we are affiliated as a managing general agent (MGA). We, therefore, act as an agent earning commissions from the premiums charged by the insurance company.

We believe the material steps for Pineapple Insurance to grow form its early stages of development are as follows:

1. To introduce the services offered by Industrial Alliance and to serve the Users on our platform, MyPineapple, is to market these services, create a knowledge base for them to understand and pass on the learning to their customers, create a support structure for both Users and Users’ customers.

2. Set up an internal infrastructure for the management and offering of these services, i.e. hire a senior management person to manage the operational affairs and thereafter additional personnel, as needed when the business grows. The additional personnel will be mostly sales commissionable personnel with a retainer.

Pineapple Insurance officially launched in October 2024, marking a significant milestone in Pineapple Financial’s diversification strategy. The costs anticipated for Pineapple Insurance are largely tied to marketing efforts, human capital, and platform development. Human capital costs include a fixed expense for senior leadership, along with variable costs for additional personnel as the business scales. With the strategic integration of Pineapple Insurance into the MyPineapple platform, our development costs are aimed at ensuring seamless client experiences and operational efficiency.

The growth timeline for Pineapple Insurance is projected at 12 to 24 months post-launch, reflecting strong initial demand and the effectiveness of our comprehensive go-to-market strategy. This timeline is contingent upon the effectiveness of marketing campaigns, customer adoption of the services offered by Industrial Alliance, and the competitiveness of pricing and premiums. The early success of our launch indicates promising customer acceptance, supported by focused efforts to educate users on product variations and benefits. These efforts are expected to accelerate market penetration and drive sustained growth for this subsidiary.

InsurTech

MyPineapple is a key reason for our success and has the ability to drive interested and timely insurance prospects to a replicated module that we have built in order to streamline and manage the customer flow for insurance products. The process is designed to create a unique synchronicity between the client obtaining a mortgage approval and insurance approval.

Combined, the simplicity of the two platforms with its connectivity and integrations will allow Pineapple Insurance to successfully process and approve insurance applications.

We have also created client segmentations and retention programs to ensure that we can maximize our database of over 150,000 potential clients.

Growth Strategy

Brokerage Services

We aim to gain further market share and consumer adoption by focusing on the following areas of growth:

1. Increase Agent Revenue From Optimized Analytics: We will continue to analyze past borrower data to determine opportunities to beneficially re-service them in the future, potentially creating revenue generating activities and significantly enhancing the borrower experience.

2. Added Product Suite - Insurance. As discussed above, we are establishing an insurance channel that provides borrowers with a full suite of insurance products, which we believe will increase revenue.

3. National Expansion: We expect to continue to expand our business and operations into current jurisdictions along with new provinces such as British Colombia and Quebec.

4. Borrower-Facing Technology. We believe MyPineapple will be a marketplace where clients can select from a variety of mortgage products that will suit their individual needs while tracking the progress and status of the transaction for the life of the mortgage and beyond.

In order to achieve our objectives and goals, Pineapple Insurance will focus on four main areas:

1. Insurance originations: Our files will be obtained exclusively through the Pineapple Financial referral network. This will be achieved through technology integration where Pineapple Insurance agents are immediately notified of a mortgage approval which requires an insurance option. Our agents will be highly trained in an effort to service the growth of our referral network. Consistency in service level and approach is key to building our brand.

2. Emphasizing core values: Servicing our clients, maintaining relationships, ongoing and continued support, education and training, ongoing lines of communication between mortgage agent and insurance agent and ensuring a smooth and efficient closing process. We expect our agents to conduct themselves with the highest level of professionalism and carry out the fundamental and core values of Pineapple Insurance at all times.

3. Hiring and training insurance agents: We will follow and adhere to strict hiring and training policies as set out in our training manuals. Development of education and training programs working in conjunction with our partners. Ensuring that we are consistently working on recruiting top performing insurance agents that will be able to meet the growth and scale of the needs of the Company.

4. Technologies and relationship management tools: We will be replicating and customizing our robust MyPineapple system for data transfer and client management. This will be broken into the following areas:

● Operational Excellence: notifying insurance agents at the optimal time to increase conversion metrics and customer satisfaction. Integration of client data so the process is convenient for all involved parties. Visibility of status and automations of workflow and requirements;

● Client Relationship Management (CRM): Advancing client relationships towards application indication, application completion and client retention; and

● Acquisition: marketing funnels to leverage the overall database and identity opportunities from older missed opportunities.

Markets for our Services

Brokerage Services

The clients for our Brokerage Services include mortgage agents, brokers, sub-brokers, brokerages and consumers. Our customer activity is intrinsically linked to the health of the real estate or commercial markets generally, particularly in Canada.

Strong housing demand during 2020, 2021 and the first quarter of 2022 positively impacted the seasonal variations. With the onset of inflationary pressures around the globe, not only the seasonality but the normal trends of the housing markets have declined with the increase of interest rates. Although our business may be negatively impacted, we believe our multiple channels of revenue help to mitigate any such impact.

In alignment with the Canadian government’s commitment to improving housing affordability and accessibility, several new housing measures have been introduced to support homeowners and first-time buyers. These include enabling homeowners to refinance their mortgages to construct secondary rental suites and borrowing up to 90% of their home’s value with a 30-year amortization period. Additionally, the mortgage insurance price limit has been increased to $2 million, ensuring broader access to financing across Canada’s diverse housing markets.

The government has also proposed consultations on taxing vacant land to encourage development and incentivize landowners to build homes. Collaboration with provinces, territories, and municipalities is underway to implement these measures effectively. Starting December 15, 2024, two key rules will further aid affordability: 30-year mortgage amortizations will become available to all first-time homebuyers and buyers of new-build properties, and the price cap for insured mortgages will rise to $1.5 million from $1 million.

Moreover, the federal government has expanded the Canada Public Land Bank by adding 14 underused federal properties, bringing the total to 70. These properties across major cities are slated for affordable housing developments. This initiative supports the government’s broader plan to unlock public lands for housing and address the growing demand for homes while strengthening Canadian communities.

These measures, alongside the influx of new immigrants and the rising demand for home renovations, refurbishments, and innovative financing solutions, create a favorable environment for Pineapple Financial Inc. to continue expanding its offerings and capitalizing on these growth opportunities.

The insurance market for Pineapple Insurance is focused around growth in the Canadian mortgage landscape as well as market share growth for Pineapple Financial.

● Real estate investors: we are able to consolidate multiple mortgage amounts into one insurance policy to help minimize risk if an investor has multiple properties.

● Residential Home purchase: with Canadian housing prices hitting all-time highs, we will help clients provide insurance to fill the gap between their current coverage and the mortgage amount

● Refinance: can help clients reduce existing coverage or apply/consolidate if they require additional coverage.

● Reverse Mortgage: these clients can use the income from the reverse mortgage to help plan their final expense through insurance as well as enrich their retirement years.

● Switch: transferring to another lender at renewal. The insurance we offer is not tied to the lender directly and can assist clients in locking in their rates long term when they can still qualify for insurance

● Renovation and construction: Clients will be able to access their cash values in their permanent insurance policies to help fund their renovations and construction projects. If additional financing is required, we can provide the added insurance coverage needed.

● Self-Employed: As large numbers of Canadians move into business for themselves, we have found a great need for an insurance product that can suit their needs since they generally do not have a company benefits plan. Income protection will also be a key component of our business here.

● Commercial Mortgages: We can provide the proper insurance to clients for the right amount of coverage and timeline for one or multiple investors. Coverages can go up to $20 million.

● Private Lending: Customized insurance can be provided to private lenders who may have a different set of circumstances in terms of investment type and timeline horizon.

● High Risk Health & Uninsurable: We can offer guaranteed issue insurance to clients who may have declining health or were previously declined for insurance in the past.

Pineapple Financial Inc. and Mortgage Market Dependency

As of November 2024, Canada’s mortgage market continues to demonstrate resilience despite ongoing challenges. According to the Bank of Canada, the total residential mortgage market is valued at over $1.6 trillion, driven by population growth, increasing borrower demand, and evolving consumer sentiment. This figure excludes mortgages held by provincially regulated entities such as credit unions and mortgage investment corporations.

Mortgage lenders offer a broad range of products, including fixed and variable rates, varying terms, and flexible amortization periods. Recent interest rate cuts by the Bank of Canada have rejuvenated the market, improving affordability for new buyers and creating opportunities for existing homeowners to refinance or renew at more favorable terms. The practice of negotiating discounted rates remains prevalent, highlighting the importance of mortgage brokers in securing competitive deals for clients.

Mortgage brokers are critical intermediaries, leveraging their volume-based bargaining power to erode lender price discrimination and secure advantageous rates. These professionals are provincially regulated and must meet stringent licensing and training requirements. While the barriers to entry remain relatively low, successful brokers rely on experience, negotiating skills, and technological support to thrive in an increasingly competitive market.

Key trends currently influencing the market include:

● Renewals Surge: Over 30% of Canadian mortgages are expected to renew within the next 12 months, a significant driver of market activity.

● Housing Shortages: A growing population, combined with limited housing supply, has led to increased pressure on the market, with demand consistently outstripping available inventory.

● Government Policies: Recent adjustments, such as the introduction of a 30-year amortization period for insured mortgages and incentives for affordable housing, have bolstered consumer confidence and created new opportunities.

● Consumer Sentiment: Improved confidence, spurred by rate cuts and stabilizing economic conditions, has increased buyer activity despite affordability challenges.

● Technology Adoption: Platforms like MyPineapple are transforming the brokerage landscape by streamlining processes and providing brokers with data-driven tools to enhance efficiency and client satisfaction.

Industry Growth Strategy

Our growth strategy focuses on organic expansion, targeting increased market share through:

1.Recruitment: We have successfully recruited a significant number of Field Agents and Users, driving a growth rate higher than many competitors. By leveraging detailed insights into competitive models, we have tailored our value proposition to attract and retain top talent.

2.Technological Integration: Our proprietary platform, MyPineapple, empowers brokers with tools to increase sales volume, productivity, and efficiency. This system also supports the seamless integration of complementary services, such as insurance products, creating additional revenue streams and enhancing the overall client experience.

3.Policy Alignment: By aligning our offerings with government initiatives to support housing affordability and address shortages, we have positioned ourselves as a key player in addressing critical market needs.

4.Focus on Renewals and Refinances: With a large portion of the mortgage market up for renewal in the next year, we have tailored solutions to help brokers optimize their client retention and capitalize on refinancing opportunities.

Our strategy is underpinned by a commitment to delivering superior value, leveraging data and insights to support broker success, and maintaining flexibility to adapt to evolving market conditions. This approach ensures we remain a leader in the Canadian mortgage and brokerage industry.

Subsequent to August 31, 2025, the Company entered into several material financing and digital-asset transactions. Management has evaluated these events in accordance with ASC 855,Subsequent Events, and determined that they represent non-recognized subsequent events require ing disclosure but no adjustment to the consolidated financial statements as of and for the year ended August 31, 2025.

On September 2, 2025, the Company entered into a Securities Purchase Agreement with certain accredited investors to issue 24,642,700 subscription receipts at an offering price of US $3.80 per subscription receipt, with respect to certain purchasers, and US $4.16 per subscription receipt, with respect to certain purchasers.

The private placement closed on September 4, 2025, raising approximately US $100 million in aggregate proceeds consisting of cash and Injective (INJ) tokens, all of which are held in escrow pending satisfaction of specified escrow release conditions under the Subscription Receipt Agreement.

On October 31, 2025, shareholders approved the issuance of the underlying common shares. The Company is preparing a registration statement on Form S-1 to register the resale of approximately 25.7 million shares, including those issuable upon exercise of associated warrants. Escrowed funds will be released upon SEC effectiveness of the registration statement and NYSE American approval of listing of the underlying shares.

On September 15, 2025, the Company executed a Master Loan and Security Agreement with Voltedge Finance Inc., providing for a revolving credit facility of up to US $15.0 million. As of November 2025, US $11.4 million had been drawn under the facility and invested in INJ tokens as part of the Company’s digital-asset treasury strategy. The facility is secured by a corporate guarantee from Cooppers Financial Group and pledges over certain digital-asset holdings.

On September 4, 2025, the Company entered into a Common Stock Purchase Agreement with White Lion Capital LLC, establishing an equity line of credit of up to US $250 million. The agreement allows the Company, at its discretion, to issue and sell common shares over a 24-month period, subject to volume and pricing limitations. As of the date of issuance of these financial statements, no shares have been issued, and the arrangement has not yet been registered with the SEC.

Management concluded that these transactions occurred after year-end and therefore did not require adjustment to the accompanying consolidated financial statements. The Company will continue to monitor subsequent developments related to the escrow releases, SEC registration processes, and loan facility utilization for disclosure in future filings.

Industry Overview

The Canadian Mortgage and Mortgage Brokerage Industry

The Canadian mortgage market represents one of the largest and most stable segments of the national financial system, with residential mortgage credit exceeding $1.8 trillion as of 2025, according to data from the Bank of Canada. This total does not include mortgages held by provincially regulated entities such as credit unions or mortgage investment corporations.

Mortgage lenders in Canada offer a broad range of products featuring fixed or variable interest rates, varying terms and amortization periods, and differing provisions for pre-payments, rate holds, and other features. Interest rates are typically renegotiated every three to five years. While lenders post benchmark rates, actual mortgage pricing is widely negotiated—a practice referred to as “discounting”—which has become an established norm across the industry. This approach enables lenders to offer customized pricing based on borrower risk profiles and market conditions.

This environment has elevated the role of the independent mortgage broker as a key intermediary between borrowers and lenders. Brokers leverage their lender relationships and market insight to secure competitive rates and terms for their clients. In return for a fee, typically paid by the lender, brokers help borrowers navigate an increasingly complex rate and qualification environment. Mortgage brokers are provincially regulated and must meet licensing and continuing-education standards. Although barriers to entry remain modest, a broker’s ability to negotiate advantageous terms is closely tied to their volume, reputation, and lender relationships.

Pineapple’s Market Position and Growth Strategy

Pineapple’s growth strategy focuses on expanding market share organically by increasing the number of mortgages funded annually and strengthening our network of mortgage professionals. Our approach emphasizes recruitment, retention, and empowerment of high-performing Field Agents through superior technology, marketing support, and operational efficiency.

Our proprietary platform, MyPineapple, is designed to enhance agent productivity and client service through advanced deal management tools, marketing automation, and real-time data analytics. This digital infrastructure allows our agents to process applications more efficiently, improve client conversion, and increase overall sales volume.

We continue to invest in recruitment and training initiatives that have positioned Pineapple among the fastest-growing mortgage brokerages in Canada. By maintaining a deep understanding of competing brokerage models, we continually refine our value proposition to attract and retain top-performing agents.

Our long-term vision is to establish Pineapple as Canada’s leading digital-first mortgage platform, connecting brokers, lenders, and consumers through a unified ecosystem built on transparency, technology, and trust. Through innovation and scale, we aim to strengthen our competitive position and create sustained value for our stakeholders.

Competitive Conditions

Regulatory backdrop.

OSFI’s Guideline B-20 has governed residential mortgage underwriting for federally regulated lenders since January 1, 20181. In November 2024, OSFI exempted uninsured “straight-switch” renewals between federally regulated lenders from the prescribed minimum qualifying rate (MQR) when the loan amount and amortization 2 do not increase 3 Separately, the federal government introduced policy changes effective in 2024–2025, including permitting 30-year amortizations for insured mortgages for first-time buyers of newly built homes (effective August 1, 2024) increasing the Home Buyers’ Plan (HBP) withdrawal limit to $60,000 (for withdrawals after April 16, 2024) . In this environment, consumers continue to seek broker guidance to navigate product terms, renewals, and rate complexity; CMHC’s Mortgage Consumer Surveys highlight sustained demand for professional advice across buying, renewing, and refinancing cohorts.

Structural drivers of broker usage.

● Underwriting stringency and evolving supervisory expectations sustain demand for broker intermediation and alternative product access.

● Product complexity and segmented borrower profiles heighten the value of multi-lender comparison and advice.

● Renewals and switches remain an important activity channel for brokers, aided by the 2024 MQR change for uninsured straight switches.

● Digital expectations favor platforms that centralize documents, credit data, and lender connectivity for faster turn times.

Primary Competitors

1.Traditional mortgage brokerages. National networks and franchise systems with established lender relationships and scale (e.g., Dominion Lending Centres, Verico, Mortgage Alliance, Centum).

2.Digital mortgage companies. Direct-to-consumer offerings emphasizing online origination while funding through major lenders or captive entities (e.g., Nesto, Homewise).

3.Mortgage technology providers. Point-solution vendors for specific workflow steps (document intake, pricing, underwriting support) that require integration by legacy firms.

Competitive Advantages

Distribution and advice. Broad panel access across banks, trust companies, and mortgage finance companies enables product fit for purchase, refinance, switch, and alternative-credit scenarios; Field Agents are trained to align recommendations with client objectives and total cost of borrowing.

Platform and data. PineappleONE centralizes lead routing, CRM, document collection, compliance workflows, lender connectivity, and funded-deal analytics. Data models segment clients and surface retention/cross-sell opportunities via actionable signals and automated reminders. Education and knowledge resources support file quality, lender fit, and compliance. Role-based access controls and audit trails are designed to strengthen data integrity and reporting.

Operations. Centralized pre-underwriting and processing support can improve conversion and funding ratios while allowing Field Agents to focus on acquisition and advice. Marketing automation and segmented communications reduce acquisition costs and enhance lifetime value.

Digital Asset Treasury Strategy (Treasury Strategy) and On-Chain Development

**Digital Asset Treasury (Treasury Strategy).**We have established the board-supervised Treasury Strategy program to support research, ecosystem partnerships, and technology experimentation. The Treasury Strategy is segregated from core brokerage operations and is governed by policies addressing custody, valuation, financial reporting, volatility limits, and disclosure. The Treasury Strategy does not involve customer funds.

1 OSFI — Final Revised Guideline B-20 (effective Jan. 1, 2018): https://www.osfi-bsif.gc.ca/en/guidance/guidance-library/final-revised-guideline-b-20-residential-mortgage-underwriting-practices-procedures. OSFI

2 OSFI — Exemption of MQR for uninsured “straight-switch” renewals (announcement, Nov. 21, 2024): https://www.osfi-bsif.gc.ca/en/guidance/guidance-library/osfi-exempts-uninsured-mortgage-straight-switches-prescribed-mqr-implements-portfolio-lti-limits. OSFI

3 OSFI — Exemption of MQR for uninsured “straight-switch” renewals (announcement, Nov. 21, 2024): https://www.osfi-bsif.gc.ca/en/guidance/guidance-library/osfi-exempts-uninsured-mortgage-straight-switches-prescribed-mqr-implements-portfolio-lti-limits. OSFI

**On-chain mortgage development.**We are conducting R&D on using distributed-ledger technologies for discrete mortgage-lifecycle elements (e.g., identity/document attestations, collateral and lien registries, servicing data integrity, investor reporting). These initiatives are exploratory and non-revenue-generating; any deployment will require successful technical validation, market acceptance, appropriate regulatory permissions, and robust privacy, security, and compliance controls.

Emerging competitive set.

As mortgage technology evolves, we expect competition from fintechs, infrastructure providers, and financial institutions pursuing tokenization, data-sharing standards, or real-time settlement use cases. We believe our combination of active brokerage distribution, proprietary workflow software, and compliance infrastructure positions us to evaluate and selectively pilot on-chain capabilities while maintaining client and regulatory safeguards.

Specialized Skill and Knowledge

Our business requires specialized skills and knowledge, which include, but are not limited to, expertise related to mortgage underwriting, mortgage originations, private lending, business development, marketing and business strategy development. Our executive and management team has a strong background and significant experience and expertise in these areas. Our team also possesses specialized skills in data architecture, software development, programming and coding, finance and accounting, automations and process, training and education. Additionally, we currently rely upon, and expect to continue to rely upon, various legal and financial advisors and consultants and others in the operation and management of our business.

Intangible Assets

Our business relies heavily on the continued development, functionality, and security of our proprietary technology platform, Pineapple Plus, which is now fully developed and maintained in-house. The Company no longer utilizes the Salesforce platform and has transitioned entirely to internally controlled systems and infrastructure. Pineapple Plus has been architected through a combination of internal development resources and multiple specialized third-party development partners; however, no single developer or vendor has access to the platform’s complete source code or architecture. This diversified development structure enhances system security and reduces reliance on any single external contributor.

We protect the proprietary components of Pineapple Plus primarily through trade secrets, internal controls, and contractual confidentiality obligations, rather than registered intellectual property rights. All employees, consultants, and advisors with access to our platform or related information are subject to confidentiality and non-disclosure agreements designed to protect our technology assets and other proprietary information.

Despite these protections, confidentiality agreements may not always prevent unauthorized use or disclosure of sensitive information, and the remedies available in the event of a breach may be inadequate. If we are unable to effectively safeguard our proprietary technology and trade secrets, our competitive position and the value of our platform could be materially impacted.

Material Contracts

Affiliation Agreements

We enter into affiliation agreements with Affiliate Brokers, pursuant to which we and the Affiliate Broker enter into an affiliation relationship with the intention of jointly marketing mortgage brokerage and other financial services as affiliated entities, sometimes referred to as “white labelling”, which allows the Affiliate Broker to sell a mortgage that is branded with its company name to its own client base. Pursuant to these affiliation agreements, we generally receive a fixed commission from the Affiliate Broker for any mortgage transaction where the Affiliate Broker has acted as the mortgage broker for the borrower. In general, these affiliation agreements have an indefinite term and may be terminated by either party upon thirty days written notice.

Asset Management Agreement

Pursuant to the Securities Purchase Agreement, on September 4, 2025, the Company entered into an Asset Management Agreement (the “Asset Management Agreement”) with Canary Capital Group LLC (the “Asset Manager”). Under the Asset Management Agreement, the Asset Manager has been appointed to provide certain asset management services with respect to cryptocurrency assets acquired by the Company in connection with the Private Placement (the “Account Assets”) maintained with one or more custodians or cryptocurrency wallet providers acceptable to the Asset Manager. Such asset management services will commence when the Subscription Receipt Agent has (i) notified the INJ Escrow Agent that all Escrow Release Conditions have been satisfied or waived and (ii) has instructed the INJ Escrow Agent to deem that title to the INJ proceeds of the Private Placement be transferred to the Company, with 30% of such assets to be managed by the Asset Manager and 70% of the assets to be managed by the Advisor as a sub-advisor under the Asset Management Agreement.

As consideration for the Asset Manager’s services, the Company will pay an asset-based fee equal to 1% per annum of the Account Assets, which shall be calculated and paid at the end of each quarter, as determined by the Asset Manager in a commercially reasonable manner based on available prices on Coinmarketcap.com. The Company may make no more than one withdrawal from the Account Assets per calendar quarter, and each such withdrawal shall not exceed $10,000 in value of INJ during the first year. Thereafter, more frequent withdrawals of more than $10,000 can be made for legitimate business purposes if such withdrawal is pre-approved by the independent members of the Board, provided that the Company cannot make a withdrawal of more than 50.1% of the Account Assets without the prior approval of a majority of the stockholders of the Company. The Asset Management Agreement continues in effect until terminated for cause by the Company upon thirty (30) days’ prior written notice or terminated for cause by the Asset Manager upon thirty (60) days’ prior written notice. The Asset Management Agreement contains customary representations, indemnification provisions, confidentiality obligations, and a non-exclusivity clause. The Asset Management Agreement limits the liability of the Asset Manager to the Company for losses arising under the agreement to cases of willful misconduct, gross negligence, fraud or material breach of contract.

Trading Advisory Agreement

On September 4, 2025, the Company entered into a Trading Advisory Agreement (the “Trading Advisory Agreement”) with Monarq Asset Management LLC (the “Advisor”). Under the Trading Advisory Agreement, the Company appoints the Advisor to manage the investment of all digital assets, digital asset derivatives, cash and other assets contained in the Account (as defined in the Trading Advisory Agreement) established by the Company with Bitgo Trust Company, Inc. The Trading Advisory Agreement continues in effect until the earlier of: (i) termination by either party for upon the occurrence of a material breach that is not cured within fifteen days of notice from the non-breaching party, or (ii) the third anniversary of the Trading Advisory Agreement, provided that the Trading Advisory Agreement will be automatically renewed for successive one-year periods unless either party provides written notice of its intention not to renew at least thirty days prior to the expiration of such term. The Company may make no more than one withdrawal from the Account Assets per calendar quarter, and each such withdrawal shall not exceed $10,000 in value of INJ during the first year. Thereafter, more frequent withdrawals of more than $10,000 can be made for legitimate business purposes if such withdrawal is pre-approved by the independent members of the Board, provided that the Company cannot make a withdrawal of more than 50.1% of the Account Assets without the prior approval of a majority of the stockholders of the Company.

The services of the Advisor under the Trading Advisory Agreement will commence when the Subscription Receipt Agent has (i) notified the INJ Escrow Agent that all Escrow Release Conditions have been satisfied or waived and (ii) has instructed the INJ Escrow Agent to deem that title to the INJ proceeds of the Private Placement be transferred to the Company, with such assets to be managed by the Asset Manager and the Advisor.

As consideration for the Advisor’s services, the Company will pay to the Advisor a quarterly management fee equal to 0.25% (a 1.0% annual rate) of the Account Equity (as defined in the Trading Advisory Agreement) as of the beginning of each calendar quarter regardless of whether there are realized or unrealized profits with respect to the account. The Trading Advisory Agreement includes customary representations and warranties and confidentiality provisions, as and provides for indemnification of the Advisor by the Company subject to exclusions for bad faith, gross negligence or willful misconduct by the Advisor.

Common Stock Purchase Agreement

On September 4, 2025, the Company entered into a Common Stock Purchase Agreement (the “ELOC Purchase Agreement”) with White Lion Capital, LLC (“White Lion”), whereby the Company has the right, but not the obligation, to sell to White Lion, and White Lion is obligated to purchase, up to an aggregate of $250,000,000 (the “Commitment Amount”) Common Shares.

The Company does not have a right to commence any sales of Common Shares to White Lion under the ELOC Purchase Agreement until all conditions to the Company’s right to commence sales, as set forth in the ELOC Purchase Agreement, have been satisfied, including that a registration statement covering the resale of such shares is declared effective by the Commission. No such registration statement has been filed and, as a result, the Company does not have right to commence the sale of Common Shares to White Lion. During the twenty four (24) months following the effective date of the ELOC Purchase Agreement, we are prohibited from entering into any other “equity line” or substantially similar facility in which an investor is obligated to purchase our securities over time at prices based on the then-current market price without White Lion’s prior written consent, except for at-the-market offerings through a registered broker-dealer and issuances upon conversion or exercise of existing derivative securities.

The ELOC Purchase Agreement contemplates that the purchase price for Common Shares sold to White Lion will be market-based and determined by the type of Purchase Notice (as defined in the ELOC Purchase Agreement) issued: under rapid purchase notices the price will be tied to the lowest traded market price at specified times (with one rapid option effectively at market and the other at a 1% discount), and under regular purchase notices the price will be a discounted percentage of the lowest daily volume-weighted average price during the valuation period (approximately a 2.5%–3% discount based on the Company’s cumulative investment level as set forth in the ELOC Purchase Agreement).

If trading in our common shares is suspended, halted, or our shares are delisted during an active Purchase Notice under the ELOC Purchase Agreement, White Lion will purchase the shares subject to that notice at a price of $0.01 per share.

The ELOC Purchase Agreement prohibits the Company from directing White Lion to purchase any Common Shares if those shares, when aggregated with all other Common Shares then beneficially owned by White Lion (as calculated pursuant to Section 13(d) of the Securities Exchange Act of 1934, as amended), would result in White Lion beneficially owning more than 4.99% of the outstanding Common Shares (the “Beneficial Ownership Limitation”), which may be increased to 9.99% at White Lion’s discretion upon 61 days’ prior written notice.

In consideration for White Lion’s execution and delivery of, and agreement to perform under the ELOC Purchase Agreement, the Company sent to White Lion a number of Injective Tokens (INJ) equal to $1,500,000 divided by the lowest trade price of the token seen on Coinbase three (3) hours prior to delivery of the token (the “Commitment Fee”).

Concurrently with the ELOC Purchase Agreement, the Company and White Lion entered into the Registration Rights Agreement.

Changes to Contracts

The Company does not expect its business to be affected in the current financial year by renegotiation or termination of contracts or sub-contracts.

Regulatory Environment

Brokerage License Requirements

In order to operate its mortgage broker business, we must remain duly licensed as a mortgage broker to deal and trade in mortgages in accordance with the Mortgage Brokerages, Lenders and Administrators Act, 2006 (Ontario), as amended (the “MBLA Act”). We have had our mortgage brokerage license since November 2016 and it has been renewed each year without issue. We will be subject to similar legislation and license requirements in the other provinces in Canada where we intend to expand.

In accordance with the MBLA Act, individuals, including directors, officers, partners, directors and officers of corporate partners, employees or agents of a mortgage brokerage company, such as the Company, who are engaged in dealing mortgages or trading in mortgages on its behalf must obtain a mortgage broker or mortgage agent license. A mortgage broker or agent license authorizes an individual to work for only the mortgage brokerage company named under the license. An individual cannot be licensed to work for more than one mortgage brokerage company. The Superintendent of Financial Services will use the information obtained in a mortgage broker license application to determine whether an applicant meets the prescribed eligibility requirements and is suitable for a license. The applicant will be required to submit documents to support certain pieces of information about the business.

Insurance Regulation

Pineapple Insurance is subject to federal, as well as provincial and territorial, regulation in Canada in the provinces and territories in which they underwrite insurance/reinsurance. The Office of the Superintendent of Financial Institutions (“OSFI”) is the federal regulatory body that, under theInsurance Companies Act (Canada) (the Insurance Companies Act”), prudentially regulates federal Canadian and non-Canadian insurance and reinsurance companies operating in Canada. Pineapple Insurance is licensed to carry on insurance business by OSFI and in each province and territory.

Under the Insurance Companies Act, Pineapple Insurance is required to maintain an adequate amount of capital in Canada, calculated in accordance with a test promulgated by OSFI called the Minimum Capital Test. Under the Insurance Companies Act, approval of the Minister of Finance (Canada) is required in connection with certain acquisitions of shares of, or control of, Canadian insurance companies such as Pineapple Insurance, and notice to and/or approval of OSFI is required in connection with the payment of dividends by or redemption of shares by Canadian insurance companies such as Pineapple Insurance.

Other Regulations

In addition, the Company must comply with all federal, provincial and municipal laws that affect a Canadian business including employment, workers’ compensation, insurance, corporate, and tax laws and regulations.

Bankruptcy and Similar Procedures

The Company has not had any bankruptcy (whether voluntary or otherwise), receivership or other similar proceedings instituted by it or against it since its incorporation nor are any such proceedings being contemplated or threatened in the foreseeable future.

Material Restructuring Transactions

Pineapple has not completed any material restructuring transactions since incorporation.

Incorporation

The Company was incorporated under the Business Corporations Act (Ontario) on October 16, 2015 under the name “2487269 Ontario Limited” (doing business under the name of Capital Lending Centre). On June 16, 2021, the Company changed its name to “Pineapple Financial Inc.” and on February 14, 2023, the Company continued out of the jurisdiction of Ontario under the Business Corporations Act (Ontario) and into the federal jurisdiction of Canada under the Canada Business Corporations Act.

The Company’s head office is located at Unit 200, 111 Gordon Baker Road, North York, Ontario M2H 3R1 and its registered and records office is located at 67 Mowat Avenue Suite 122, Toronto, Ontario M6K 3E3.

Corporate Structure

The Company has two wholly owned subsidiaries: Pineapple Insurance Inc. (“Pineapple Insurance”) and Pineapple National Inc. (“Pineapple National”). Pineapple Insurance was incorporated under the Business Corporations Act (Ontario) on December 14, 2016, under the name “CLC Insurance Inc.” and on July 12, 2021, changed its name to “Pineapple Insurance Inc.”. Pineapple Insurance has a registered and records office located at Suite 200, 111 Gordon Baker Road, North York, Ontario M2H 3R1. Pineapple National Inc. was incorporated under the Canada Business Corporations Act on November 9, 2021, with a registered and records office located at 2600 – 1066 West Hastings Street, Vancouver, British Columbia V6C 2T5.

The Company also holds 5% of the issued and outstanding Class A Shares of 4313305 Canada Inc. (doing business as MCommercial) and 5% of the issued and outstanding shares of 7326904 Canada Inc. (doing business as Mortgage Alliance Corporation).