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Pineapple Financial Inc. PAPL US Equity

Financials · CIK 1938109
$1.00
-0.05 (-4.76%)
USD · as of 2026-08-28 · marketstack

Pineapple Financial Inc. (NYSE: PAPL), an SEC filer in Finance Services, closed at $1.00, -4.8%, on 2026-08-28, with a market cap of $27M as of 2026-08-27, a return on equity of -322.6%, a net margin of -121.8% and 3-year sales growth of -6.0%. Institutional ownership, earnings history and filed financials are on the tabs below.

PAPL · 10-K · period ended 2025-08-31

← all PAPL documents
filed 2025-12-03 · EDGAR original ↗

Our rendering of the filing — original pagination and typography are not reproduced, and tables are reduced to their short label cells (the figures live on FA). Nothing is summarized: every line below is the filing's own text.

blocks 1600 of 4,654346k characters rendered

UNITED

STATES

SECURITIES

AND EXCHANGE COMMISSION

Washington,

D.C. 20549

FORM

10-K

☒ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For

the fiscal year ended August 31, 2025

☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For

the transition period from ______ to ______

Commission

file number 001-41738

PINEAPPLE

FINANCIAL INC.

(Exact

Name of Registrant as Specified in Its Charter)

Unit 200, 111 Gordon Baker Road

North York, Ontario M2H 3R1

(Address of principal executive offices, including ZIP code)

(Registrant’s telephone number, including area code)

Securities

registered pursuant to Section 12(b) of the Exchange Act:

Title of each class Trading Symbol Name of exchange on which registered

Common Shares, no par value PAPL NYSE American

Indicate

by check mark if the registrant is a well-known seasoned issuer, as defined in Rule 405 of the Securities Act. Yes ☐ No ☒

Indicate

by check mark if the registrant is not required to file reports pursuant to Section 13 or Section 15(d) of the Act. Yes ☐ No ☒

Indicate

by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange

Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2)

has been subject to such filing requirements for the past 90 days. Yes ☐ No ☒

Indicate

by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule

405 of Regulation S-T (§ 232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant

was required to submit such files). Yes ☒ No ☐

Indicate

by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting

company, or an emerging growth company. See definition of “large accelerated filer,” “accelerated filer,” “smaller

reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

Large accelerated filer ☐ Accelerated filer ☐

Non-accelerated filer ☒ Smaller reporting company ☒

Emerging growth company ☒

If

an emerging growth company, indicate by check mark 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. ☐

Indicate

by check mark whether the registrant has filed a report on and attestation to its management’s assessment of the effectiveness

of its internal control over financial reporting under Section 404(b) of the Sarbanes-Oxley Act (15 U.S.C. 7262(b)) by the registered

public accounting firm that prepared or issued its audit report. ☐

If

securities are registered pursuant to Section 12(b) of the Act, indicate by check mark whether the financial statements of the registrant

included in the filing reflect the correction of an error to previously issued financial statements. ☐

Indicate

by check mark whether any of those error corrections are restatements that required a recovery analysis of incentive-based compensation

received by any of the registrant’s executive officers during the relevant recovery period pursuant to §240.10D-1(b). ☐

Indicate

by check mark whether the registrant is a shell company (as defined by Rule 12b-2 of the Exchange Act) Yes ☐ No ☒

As

of August 31, 2025 (the last business day of the registrant’s most recently completed year end), the aggregate market value of

the registrant’s common shares held by non-affiliates of the registrant was approximately $5.391 million, based on the closing

price on that date as reported on the NYSE American LLC.

Number

of shares of common shares outstanding as of December 01, 2025 was 1,345,941.

Documents

Incorporated by Reference: None.

TABLE

OF CONTENTS

Part I

Item 1. Business 1

Item 1A. Risk Factors 16

Item 1B. Unresolved Staff Comments 38

Item IC. Cybersecurity 38

Item 2. Properties 38

Item 3. Legal Proceedings 38

Item 4. Mine Safety Disclosures 38

Part II

Item 6. [Reserved] 39

Item 7A. Quantitative and Qualitative Disclosures about Market Risk 52

Item 8. Financial Statements and Supplementary Data 54

Item 9A. Controls and Procedures 54

Item 9B. Other Information 54

Item 9C. Disclosure Regarding Foreign Jurisdictions that Prevent Inspections 54

Part III

Item 10. Directors, Executive Officers and Corporate Governance 55

Item 11. Executive Compensation 61

Item 14. Principal Accountant Fees and Services 66

Part IV

Item 15. Exhibit and Financial Statement Schedules 67

Signatures 68

i

CAUTIONARY

NOTE REGARDING FORWARD-LOOKING STATEMENTS

This

Annual Report on Form 10-K contains certain forward-looking statements within the meaning of Section 27A of the Securities Act of 1933,

as amended (the “Securities Act”), and Section 21E of the Securities Exchange Act of 1934, as amended (the “Exchange

Act”). Any statements in this Annual Report on Form 10-K about our expectations, beliefs, plans, objectives, assumptions or future

events or performance are not historical facts and are forward-looking statements. These statements are often, but not always, made through

the use of words or phrases such as “believe,” “will,” “expect,” “anticipate,” “estimate,”

“intend,” “plan” and “would.” For example, statements concerning financial condition, possible or

assumed future results of operations, growth opportunities, industry ranking, plans and objectives of management, markets for our common

stock and future management and organizational structure are all forward-looking statements. Forward-looking statements are not guarantees

of performance. They involve known and unknown risks, uncertainties and assumptions that may cause actual results, levels of activity,

performance or achievements to differ materially from any results, levels of activity, performance or achievements expressed or implied

by any forward-looking statement.

Any

forward-looking statements are qualified in their entirety by reference to the risk factors discussed throughout this Annual Report on

Form 10-K. Some of the risks, uncertainties and assumptions that could cause actual results to differ materially from estimates or projections

contained in the forward-looking statements include, but are not limited to:

● the timing of the development of future services,

● projections of revenue, earnings, capital structure and other financial items,

● statements regarding the capabilities of our business operations,

● statements of expected future economic performance,

● statements regarding competition in our market, and

● assumptions underlying statements regarding us or our business.

The

foregoing list sets forth some, but not all, of the factors that could affect our ability to achieve results described in any forward-looking

statements. You should read this Annual Report on Form 10-K and the documents that we reference herein and have filed as exhibits to

the Annual Report on Form 10-K, completely and with the understanding that our actual future results may be materially different from

what we expect. You should assume that the information appearing in this Annual Report on Form 10-K is accurate as of the date hereof.

Because the risk factors referred to on page 15 of Annual Report on Form 10-K could cause actual results or outcomes to differ materially

from those expressed in any forward-looking statements made by us or on our behalf, you should not place undue reliance on any forward-looking

statements. Further, any forward-looking statement speaks only as of the date on which it is made, and except as required by law, we

undertake no obligation to update any forward-looking statement to reflect events or circumstances after the date on which the statement

is made or to reflect the occurrence of unanticipated events. New factors emerge from time to time, and it is not possible for us to

predict which factors will arise. In addition, we cannot assess the impact of each factor on our business or the extent to which any

factor, or combination of factors, may cause actual results to differ materially from those contained in any forward-looking statements.

We qualify all of the information presented in this Annual Report on Form 10-K, and particularly our forward-looking statements, by these

cautionary statements.

ii

SUMMARY

OF RISK FACTORS

Our

business is subject to numerous risks described in the section titled “Risk Factors” and elsewhere in this prospectus. The

main risks set forth below and others you should consider are discussed more fully in the section entitled “Risk Factors”

beginning on page 15, which you should read in its entirety.

● risks associated with our digital assets and digital asset treasury

our operations could be adversely affected by possible future government legislation, policies and controls or by changes in applicable

laws and regulations;

public health crises such as the COVID-19 pandemic may adversely impact our business;

the volatility of global capital markets over the past several years has generally made the raising of capital more difficult;

risks associated with political instability and changes to the regulations governing our business operations;

our success is largely dependent on the performance of our directors and officers, Field Agents, and employees;

our Common Shares may be subject to significant price volatility;

internal controls cannot provide absolute assurance with respect to the reliability of financial reporting and financial statement preparation;

we may be unable to manage our growth;

risks associated with security breaches;

risks associated with software errors or defects;

our operations depend on information technology systems; and on continuous reliable internet access;

our business now or in the future may be adversely affected by risks outside our control;

risks associated with the Company’s reliance on strategic partnerships;

reputational risk, and

risks associated with protection of intellectual property.

iii

ITEM

1. BUSINESS

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.

Insurance

Products

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.

Insurance

Products

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.

Insurance

Products

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.

Source: SEC EDGAR (public domain) · 10-K for the period ended 2025-08-31, filed 2025-12-03 · accession 0001493152-25-025962

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