What changed in this filing

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Item 1A. Risk Factors

2025-12-03 compared with 2024-12-20 · 490 added, 199 removed, 668 unchanged (51% of the section changed)

Related to the Company

intend to use the net proceeds from the Private Placement to purchase digital assets, including INJ, the price of which has been, and

will likely continue to be, highly volatile.

Our operating results and share price may significantly fluctuate, including due to the

highly volatile nature of the price of such digital assets and erratic market movements.

intend to use the net proceeds from the Private Placement to purchase or otherwise acquire INJ and for the establishment of our digital

asset treasury operations.

Digital assets, such as INJ, generally are highly volatile assets, including as a result of shifts in market

sentiment, speculative trading, macroeconomic trends, technology-related disruptions and regulatory announcements.

In addition, digital

assets do not pay interest or other returns, unless utilized in staking or financial applications, and so the ability to generate a return

on investment from the net proceeds of any capital raisings will principally depend on whether there is appreciation in the value of

digital assets following our purchases of digital assets with the net proceeds from such capital raisings.

Future fluctuations in digital

asset trading prices may result in our converting digital assets into cash with a value substantially below what we paid for such digital

have adopted a digital asset treasury strategy with a focus on INJ, and we may be unable to successfully implement this new strategy.

have adopted a digital asset treasury primarily dedicated to INJ and potential acquisitions INJ, including through staking and other

decentralized finance activities.

There is no assurance that we will be able to successfully implement this new strategy or operate Injective-related

activities at the scale or profitability currently anticipated.

This strategic shift requires specialized employee skillsets and operational,

technical and compliance infrastructure to support INJ and related staking activities.

This also requires that we implement different

security protocols and treasury management practices.

Further, there is ongoing scrutiny and limited formal guidance from regulatory

agencies, including NYSE American and the SEC, with respect to the treatment of public company cryptocurrency strategies.

assurance that we will be able to execute this Treasury Strategy by building out the needed infrastructure within the timeframe that

we currently anticipate.

Errors by key management could result in significant loss of funds and reduced rewards.

As a result, our shift

towards INJ could have a material adverse effect on our business and financial condition.

Common Shares may trade at a discount to our net asset value, and investors could experience losses unrelated to the performance of our

underlying digital asset holdings.

market price of our Common Shares may not reflect, and at times may trade materially below, our net asset value (“ NAV ”)

A variety of factors may cause the trading price of our Common Shares to deviate from our NAV, including overall market conditions,

investor sentiment toward digital assets or our business model, the liquidity and volatility of the specific digital assets we hold,

the availability and cost of capital to market participants, the level of short interest in our Common Shares, actual or perceived governance

or operational risks, and the absence of any redemption or exchange feature that would allow shareholders to realize NAV directly.

a result, the market price of our Common Shares may be influenced by factors other than the value of our underlying assets alone and

there can be no assurance that our Common Shares will trade at or near NAV .

our Common Shares trade at a discount to NAV, investors who sell shares may receive less than the value of our underlying assets per

share, and the discount could impair our ability to raise capital on favorable terms.

We may from time to time consider capital markets

transactions, financing arrangements or other corporate actions intended to address any discount, but we are under no obligation to take

such actions and any such actions, if implemented, may be limited in scope or effectiveness.

shift towards an Injective-focused strategy requires substantial changes in our day-to-day operations and exposes us to significant operational

shift towards an INJ treasury-focused strategy, including staking and other decentralized finance activities, exposes us to significant

operational risks.

The Injective ecosystem rapidly evolves, with frequent upgrades and protocol changes that may require significant

adjustments to our operational setup.

The upgrades and protocol changes may require that we incur unanticipated costs and could cause

temporary service disruptions to the Injective network.

We may also need to employ third-party service providers in our operations, which

may introduce risks outside of our control, including significant cybersecurity risks.

Any of these operational risks could materially

and adversely affect our ability to execute the Treasury Strategy and may prevent us from realizing positive returns and could severely

hurt our financial condition.

concentration of our INJ holdings enhances the risks inherent in our Injective-focused strategy.

have and intend to purchase INJ and increase our overall holdings of INJ in the future.

The intended concentration of our INJ holdings

limits the risk mitigation that we could achieve if we were to purchase a more diversified portfolio of treasury assets, and the absence

of diversification enhances the risks inherent in our Injective-focused strategy.

the Injective network is disrupted or encounters any unanticipated difficulties, the value of INJ could be negatively impacted.

the Injective network is disrupted or encounters any unanticipated difficulties, then the processing of transactions on the Injective

network may be disrupted, which in turn may prevent us from depositing or withdrawing INJ from our accounts with our custodian or otherwise

affecting INJ transactions.

Such disruptions could include, for example:

the insolvency, business failure, interruption, default, failure

to perform, security breach, or other problems of participants, custodians, or others;

the closing of INJ trading platforms due to fraud,

failures, security breaches or otherwise;

or network outages or congestion, power outages, or other problems or disruptions affecting

the Injective network.

Any disruption of the Injective network could result in the inability of the Company to transfer or sell INJ,

and the price of INJ.

and other digital assets are novel assets, and are subject to significant legal, commercial, regulatory and technical uncertainty, which

could materially adversely affect the Company’s financial position, operations and prospects.

and other digital assets, as well as applications on blockchain networks such as Injective, are relatively novel and are subject to significant

uncertainty, which could adversely impact their price.

The application of state and federal securities laws and other laws and regulations

to digital assets and blockchain-based applications is unclear in certain respects, and it is possible that regulators in the United

States or foreign countries may interpret or apply existing laws and regulations in a manner that adversely affects the price of INJ

or other digital assets, or the ability of blockchain-based applications to operate.

federal government, states, regulatory agencies, and foreign countries may also enact new laws and regulations, or pursue regulatory,

legislative, enforcement or judicial actions, that could materially impact the price of INJ or the ability of individuals or institutions

such as us to own or transfer INJ and utilize blockchain-based applications on networks such as Injective.

For example, the U.S.

branch, the SEC, the European Union’s Markets in Crypto Assets Regulation, among others, have been active in recent years, and

in the United Kingdom, the Financial Services and Markets Act 2023 became law.

Additionally, legislative and regulatory priorities may

change depending on changes in leadership, as evidenced by recent and proposed initiatives such as the Genius Act of 2025, the anticipated

Digital Asset Market Clarity Act, and updates to the Commission’s Regulatory Flexibility Agenda.

It is not possible to predict

whether, or when, any of these developments will lead to Congress granting additional authorities to the SEC, Commodity Futures Trading

Commission (“ CFTC ”), or other regulators, or whether, or when, any other federal, state or foreign legislative bodies

will take any similar actions.

It is also not possible to predict the nature of any such additional authorities, how additional legislation

or regulatory oversight might impact the ability of digital asset markets to function or the willingness of financial and other institutions

to continue to provide services to the digital assets industry, nor how any new regulations or changes to existing regulations might

impact the value of digital assets generally and INJ specifically.

The consequences of increased regulation of digital assets and digital

asset activities could adversely affect the market price of INJ and in turn adversely affect the market price of our Common Shares.

the risks of engaging in a digital asset treasury strategy are relatively novel and have created, and could continue to create complications

due to the lack of experience that third parties have with companies engaging in such a strategy, such as increased costs of director

and officer liability insurance or the potential inability to obtain such coverage on acceptable terms in the future.

growth of the digital assets industry in general, and the use and acceptance of INJ in particular, may also impact the price of INJ and

is subject to a high degree of uncertainty.

The pace of worldwide growth in the adoption and use of the Injective network and INJ may

depend, for instance, on public familiarity with digital assets, ease of buying, accessing or gaining exposure to INJ, institutional

demand for INJ as an investment asset, the participation of traditional financial institutions in the digital assets industry, consumer

demand for INJ as a means of payment, and the availability and popularity of alternatives to INJ.

Even if growth in INJ adoption occurs

in the near or medium term, there is no assurance that INJ and the Injective network usage will continue to grow over the long term.

variety of technical factors related to the Injective blockchain could also impact the price of INJ.

The liquidity of INJ may also be

reduced and damage to the public perception of Injective may occur, if financial institutions were to deny or limit banking services

to businesses that hold INJ, provide Injective-related services or accept INJ as payment, which could also decrease the price of INJ.

liquidity of INJ may also be impacted to the extent that changes in applicable laws and regulatory requirements negatively impact

the ability of exchanges and trading venues to provide services for INJ and other digital assets.

in regulatory interpretations could require us to register as a money services business or money transmitter, leading to increased compliance

costs or operational shutdowns.

regulatory regime for digital assets in the U.S.

and elsewhere is uncertain.

The Company may be unable to effectively react to proposed

legislation and regulation of digital assets, which could adversely affect its business.

regulatory changes or interpretations require us to register as a money services business with The Financial Crimes Enforcement Network

(FinCEN) under the U.S.

Bank Secrecy Act, or as a money transmitter under state laws, we may be subject to extensive regulatory requirements,

resulting in significant compliance costs and operational burdens.

In such a case, we may incur extraordinary expenses to meet these

requirements or, alternatively, may determine that continued operations are not viable.

If we decide to cease certain operations in response

to new regulatory obligations, such actions could occur at a time that is unfavorable to investors.

states have implemented or proposed regulatory frameworks for digital asset businesses.

Compliance with such state-specific regulations

may increase costs or impact our business operations.

Further, if we or our service providers are unable to comply with evolving federal

or state regulations, we may be forced to dissolve or liquidate certain operations, which could materially impact our investors.

any of the digital assets that we hold are classified as a security, we may be subject to extensive regulation, which could result in

significant costs or force us to cease operations.

changes or interpretations that classify digital assets that we hold as a security under the Securities Act of 1933, as amended, or the

Investment Company Act, could require us to register and comply with additional regulations.

Compliance with these requirements could

impose extraordinary, non-recurring expenses on our business.

If the costs and regulatory burdens become too great, we may be forced

to modify or cease certain operations, which could be detrimental to our investors.

SEC has previously indicated that certain digital assets may be considered securities depending on their structure and use.

Future developments

could change the legal status of digital assets that we may hold, requiring us to comply with securities laws.

If we fail to do so, we

may be forced to discontinue some or all of our business activities, negatively impacting investments in our securities.

the SEC or other regulators determine that digital assets that we may hold qualify as securities, we may be required to change our operations,

wind down our operations, or register as an investment company under the Investment Company Act.

This classification would subject us

to additional periodic reporting, disclosure requirements, and regulatory compliance obligations, significantly increasing our operational

Compliance with the requirements of the Investment Company Act applicable to registered investment companies may make it difficult

for us to continue our current operations, and this would materially and adversely affect our business, financial condition and results

of operations.

In addition, if INJ or another digital asset we hold were determined to constitute a security for purposes of the federal

securities laws, we would likely take steps to reduce the percentage of INJ or such other digital assets that constitute investment assets

under the Investment Company Act.

These steps may include, among others, selling INJ that we might otherwise hold for the long term and

deploying our cash in non-investment assets, and we may be forced to sell our INJ or other digital assets at unattractive prices, or

cease our operations.

we do not currently engage in investing, reinvesting, or trading securities, and we do not hold ourselves out as an investment company,

we could inadvertently be deemed one under the Investment Company Act.

If we are unable to rely on an exclusion, we would be required

to register with the SEC, which could impose additional financial and regulatory burdens.

state regulators may conclude that the digital assets we hold are securities under state laws, requiring us to comply with state-specific

securities regulations.

States like California have stricter definitions of “investment contracts” than the SEC, increasing

the risk of additional regulatory scrutiny.

classification of digital assets that we hold as a commodity could subject us to additional CFTC regulation, resulting in significant

compliance costs or the cessation of certain operations.

current interpretations, INJ could be classified as a commodity under the Commodity Exchange Act and could be subject to regulation by

If our activities require CFTC registration, we may be required to comply with extensive regulatory obligations, which could

result in significant costs and operational disruptions.

Additionally, current and future legislative or regulatory developments, including

new CFTC interpretations, could further impact how INJ is classified and traded.

INJ are regulated as a commodity, we may be required to register as a commodity pool operator and register the Company as a commodity

pool with the CFTC through the National Futures Association.

Compliance with these additional regulatory requirements could result in

substantial, non-recurring expenses, adversely affecting an investment in our securities.

If we determine not to comply with such regulations,

we may be forced to cease certain operations, which could negatively impact our investors.

are not subject to legal and regulatory obligations that apply to investment companies such as mutual funds and exchange-traded funds,

or to obligations applicable to investment advisers.

funds, exchange-traded funds (ETFs) and their management are subject to extensive regulation as “investment companies” and

“investment advisers” under U.S.

federal and state law;

this regulation is intended for the benefit and protection of investors.

We are not subject to, and do not otherwise voluntarily comply with, these laws and regulations.

This means, among other things, that

the execution of our changes to our digital asset strategy, our use of leverage, our ability to engage in transactions with affiliated

parties and our operating and investment activities generally are not subject to the extensive legal and regulatory requirements and

prohibitions that apply to investment companies and investment advisers.

to the unregulated nature and lack of transparency surrounding the operations of many digital asset trading venues, digital asset trading

venues experience greater risk of fraud, market manipulation and other deceptive marketing practices, as well as security failures or

regulatory or operational problems than trading venues for more established asset classes, which may result in a loss of confidence in

digital asset trading venues and adversely affect the value of digital assets, and the Company’s financial position, operations

and prospects.

asset trading venues are relatively new and, in many cases, unregulated.

Furthermore, there are many digital asset trading venues that

do not provide the public with significant information regarding their ownership structure, management teams, corporate practices and

regulatory compliance.

As a result, the marketplace may lose confidence in digital asset trading venues, including prominent exchanges

that handle a significant volume of such trading and/or are subject to regulatory oversight, in the event one or more digital asset trading

venues cease or pause for a prolonged period the trading of digital assets, or experience fraud, significant volumes of withdrawal, security

failures or operational problems.

perception, a lack of stability in the broader digital asset markets and the closure, temporary shutdown or operational disruption of

digital asset trading venues, lending institutions, institutional investors, institutional miners, custodians, or other major participants

in the digital asset ecosystem, due to fraud, business failure, cybersecurity events, government-mandated regulation, bankruptcy, or

for any other reason, may result in a decline in confidence in digital assets and the broader digital asset ecosystem and greater volatility

in the price of digital assets.

The price of our listed securities may be affected by the value of our future digital asset holdings,

and the failure of a major participant in the ecosystem could have a material adverse effect on the market price of our listed securities.

historical financial statements do not reflect the potential variability in earnings that we may experience in the future relating to

our proposed holdings of digital assets.

Accordingly, it may be difficult to evaluate the Company’s business and future prospects,

and the Company may not be able to achieve or maintain profitability in any given period.

historical financial statements do not reflect the potential variability in earnings that we may experience in the future from holding

or selling digital assets.

The price of digital assets generally has historically been subject to dramatic price fluctuations and is

highly volatile.

We will need to perform an analysis each quarter to identify whether events or changes in circumstances indicate that

our digital assets are impaired.

As a result, volatility in our earnings may be significantly more than what we experienced in prior

Digital asset holdings are illiquid and cannot serve as a source of liquidity for us, subject to limited exceptions.

Historically,

the digital asset market has been characterized by significant volatility in price, limited liquidity and trading volumes compared to

sovereign currencies markets, concerns regarding pseudonymity of digital asset addresses, a developing regulatory landscape, potential

susceptibility to market abuse and manipulation, compliance and internal control failures at exchanges, and various other risks inherent

in its entirely electronic, virtual form and decentralized network.

While these risks can adversely affect holders of digital assets

generally, our exposure is distinct because we are contractually prohibited from liquidating our cryptocurrency positions, including

our INJ holdings, other than in limited circumstances in which material liquidations of our digital assets would require board and/or

shareholder approval.

As a result, we cannot sell our digital assets to meet working capital needs, respond to market dislocations, rebalance

our positions, or reduce losses during periods of heightened volatility.

Because we are unable to liquidate our digital assets, those

holdings cannot serve as a source of liquidity for us, and we must rely on cash, cash equivalents, and other external financing sources

to satisfy our obligations.

Further, digital assets we hold with our custodians and transact with our trade execution partners do not

enjoy the same protections or insurance as are available to cash or securities deposited with or transacted by institutions subject to

regulation by the Federal Deposit Insurance Corporation or the Securities Investor Protection Corporation.

Additionally, we may be unable

to enter into term loans or other capital raising transactions collateralized by our unencumbered digital assets or otherwise generate

funds using our digital asset holdings, including in particular during times of market instability or when the price of digital assets

has declined significantly.

If we are unable to raise additional capital, refinance existing obligations, or otherwise generate funds

from sources other than the sale of our digital assets, or if the value of our digital assets declines significantly while we remain

unable to sell, our liquidity, business, financial condition, and results of operations could be materially and adversely affected.

lack of legal recourse and insurance for digital assets increases the risk of total loss in the event of theft or destruction.

assets that we acquire will not be insured against theft, loss or destruction.

If an event occurs where we lose our digital assets, whether

due to cyberattacks, fraud or other malicious activities, we may not have any viable legal recourse or ability to recover the lost assets.

Unlike funds held in insured banking institutions, our digital assets are not protected by the Federal Deposit Insurance Corporation

or the Securities Investor Protection Corporation.

If our digital assets are lost under circumstances that render another party liable,

there is no guarantee that the responsible party will have the financial resources to compensate us.

As a result, we and our shareholders

could face significant financial losses.

Company will face risks relating to the custody of its digital assets.

If we or our third-party service providers experience a security

breach or cyberattack and unauthorized parties obtain access to our private keys, or if our private keys are lost or destroyed, or other

similar circumstances or events occur, we may lose some or all of our digital assets and our financial condition and results of operations

could be materially adversely affected.

expect our primary counterparty risk with respect to our INJ will be custodian performance obligations under the custody arrangements

we enter into.

A series of high-profile bankruptcies, closures, liquidations, regulatory enforcement actions and other events relating

to companies operating in the digital asset industry, the closure or liquidation of certain financial institutions that provided lending

and other services to the digital assets industry, SEC enforcement actions against other providers, or placement into receivership or

civil fraud lawsuit against digital asset industry participants have highlighted the perceived and actual counterparty risk applicable

to digital asset ownership and trading.

Legal precedent created in these bankruptcies and other proceedings may increase the risk of

future rulings adverse to our interests in the event one or more of our custodians becomes a debtor in a bankruptcy case or is the subject

of other liquidation, insolvency or similar proceedings.

assurance can be provided that our custodially held INJ will not become part of the custodian’s insolvency estate if one or more

of our custodians enters bankruptcy, receivership or similar insolvency proceedings.

Additionally, if we pursue any strategies to create

income streams or otherwise generate funds using our INJ holdings, we would become subject to additional counterparty risks.

need to carefully evaluate market conditions, including price volatility as well as service provider terms and market reputations and

performance, among others, prior to implementing any such strategy, all of which could affect our ability to successfully implement and

execute on any such future strategy.

These risks, along with any significant non-performance by counterparties, including in particular

the custodian or custodians with which we will custody substantially all of our INJ, could have a material adverse effect on our business,

prospects, financial condition, and operating results.

irreversibility of digital asset transactions exposes us to risks of theft, loss and human error, which could negatively impact our business.

asset transactions are not, from an administrative perspective, reversible without the consent and active participation of the recipient

of the transaction or, in theory, control or consent of a majority of the processing power on that digital asset network.

Once a transaction

has been verified and recorded in a block that is added to the blockchain, an incorrect transfer of digital assets or a theft of digital

assets generally will not be reversible, and we may not be capable of seeking compensation for any such transfer or theft

we plan to regularly transfer digital assets to or from vendors, consultants and services providers, it is possible that, through computer

or human error, or through theft or criminal action, such assets could be transferred in incorrect amounts or to unauthorized third parties.

the extent we are unable to seek a corrective transaction to identify the third party which has received our digital assets through error

or theft, we will be unable to revert or otherwise recover the impacted digital assets, and any such loss could adversely affect our

business, results of operations and financial condition

emergence or growth of other digital assets, including those with significant private or public sector backing, including by governments,

consortiums or financial institutions, could have a negative impact on the price of INJ and adversely affect the Company’s securities.

the launch of the Company’s proposed digital asset treasury strategy, as a result of our Injective strategy, we expect our assets

to be concentrated in INJ holdings.

Accordingly, the emergence or growth of digital assets other than INJ, including those with significant

private or public sector backing, including by governments, consortiums or financial institutions, may have a material adverse effect

on our financial condition.

There are numerous alternative digital assets and many entities, including consortiums and financial institutions,

are researching and investing resources into private or permissioned blockchain platforms.

If the mechanisms or network effects on alternative

blockchain platforms are perceived as superior to the Injective network, those digital assets could gain market share relative to Injective.

are dependent on the residential real estate market.

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higher costs, which could materially adversely affect our business, financial condition and results of operations.

If the O ffice

of the Superintendent of Financial Institutions (“OFSI”) determines that our corporate actions do not comply with

applicable Canadian law, Pineapple Insurance could face sanctions or fines, and be subject to increased capital requirements or other

requirements.

If OSFI determines Pineapple Insurance is not receiving adequate support from Pineapple under applicable Canadian law,

Pineapple Insurance may be subject to increased capital requirements or other requirements deemed appropriate by OSFI.

If the Office of the

Superintendent of Financial Institutions (“OSFI”) determines that our corporate actions do not comply with applicable Canadian

law, Pineapple Insurance could face sanctions or fines, and be subject to increased capital requirements or other requirements.

determines Pineapple Insurance is not receiving adequate support from Pineapple under applicable Canadian law, Pineapple Insurance may

be subject to increased capital requirements or other requirements deemed appropriate by OSFI.

there are extraordinary changes to Canadian statutory or regulatory requirements, we may be unable to fully comply with or maintain all

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to originate, monitor or service customer accounts or comply with contractual obligations.

are dependent upon the successful and uninterrupted functioning of our computer and data processing systems and software including MyPineapple

are dependent upon the successful and uninterrupted functioning of our computer and data processing systems and software including Pineapple Plus

as well as the customized software developed by us as part of our third-party underwriting services.

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operate in a competitive industry characterized by rapid technological change and evolving industry standards.

Our ability to attract

new customers and generate revenue from existing customers will depend largely on its ability to anticipate industry standards and trends,

respond to technological advances in its industry, and to continue to enhance existing services or to design and introduce new services

on a timely basis to keep pace with technological developments and its customers’ increasingly sophisticated needs.

of any enhancement or new services depends on several factors, including the timely completion and market acceptance of the enhancement

or new services.

Any new service we develop or acquires might not be introduced in a timely or cost-effective manner and might not achieve

the broad market acceptance necessary to generate significant revenue.

If any of our competitors implements new technologies before we

are able to implement them, those competitors may be able to provide more effective services than us at lower prices.

Any delay or failure

in the introduction of new or enhanced services could harm our business, results of operations and financial condition.

Our ability to

attract new customers and generate revenue from existing customers will depend largely on its ability to anticipate industry

standards and trends, respond to technological advances in its industry, and to continue to enhance existing services or to design

and introduce new services on a timely basis to keep pace with technological developments and our customers’ increasingly

sophisticated needs.

The success of any enhancement or new services depends on several factors, including the timely completion and

market acceptance of the enhancement or new services.

Any new service we develop or acquires might not be introduced in a timely or

cost-effective manner and might not achieve the broad market acceptance necessary to generate significant revenue.

If any of our

competitors implements new technologies before we are able to implement them, those competitors may be able to provide more

effective services than us at lower prices.

Any delay or failure in the introduction of new or enhanced services could harm our

business, results of operations and financial condition.

services are expected to embody complex technology that may not meet those standards, changes and preferences.

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a further economic slowdown, our operations, our ability to raise capital and the trading price of our securities could be adversely

With inflation now under control, the economic outlook

in Canada has improved significantly.

After peaking at 8.1% in mid-2022, inflation has steadily declined and is currently within the Bank

of Canada’s target range of 2-3%.

In response, the Bank of Canada reduced the policy interest rate by 1.25% during 2024, bringing

the rate down to 3.75%, with further reductions expected in the near future.

These reductions, combined with recent government initiatives

such as the introduction of 30-year amortizations, an increased mortgage insurance price cap of $2 million, and incentives for secondary

suite construction, are creating a more favorable environment for Canadian borrowers.

The decrease in interest rates has eased mortgage

qualification requirements, improved affordability and boosting loan originations.

Additionally, government measures to unlock public

land for affordable housing and encourage development through taxation of vacant land further contribute to a positive outlook for the

housing and mortgage markets.

inflation now under control, the economic outlook in Canada has improved significantly.

After peaking at 8.1% in mid-2022, inflation

has steadily declined and is currently within the Bank of Canada’s target range of 2-3%.

In response, the Bank of Canada reduced

the policy interest rate by 1.25% during 2024, bringing the rate down to 3.75%, with further reductions expected in the near future.

These reductions, combined with recent government initiatives such as the introduction of 30-year amortizations, an increased mortgage

insurance price cap of $2 million, and incentives for secondary suite construction, are creating a more favorable environment for Canadian

decrease in interest rates has eased mortgage qualification requirements, improved affordability and boosting loan originations.

Additionally,

government measures to unlock public land for affordable housing and encourage development through taxation of vacant land further contribute

to a positive outlook for the housing and mortgage markets.

Pineapple Financial Inc.

is well-positioned to leverage these favorable conditions, supporting borrowers

with innovative solutions and capitalizing on renewed growth opportunities in the housing sector.

is well-positioned to leverage these favorable conditions,

supporting borrowers with innovative solutions and capitalizing on renewed growth opportunities in the housing sector.

decline in the global macroeconomic outlook, including as a result of Russia’s invasion of Ukraine and the threat, or outbreak

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growth prospects.

Company’s intellectual property rights are valuable, and any failure or inability to protect them could adversely affect its business.

Company’s intellectual property rights are valuable, and any failure or inability to protect them could adversely affect our

commercial success depends to a significant degree upon its ability to develop new or improved technologies, instruments and services,

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as the laws of Canada or the United States.

depend on highly skilled personnel to grow and operate its business.

If we are not able to hire, retain, and motivate our key personnel,

our business may be adversely affected.

depend on highly skilled personnel to grow and operate our business.

If we are not able to hire, retain, and motivate our key

personnel, our business may be adversely affected.

success is currently largely dependent on the performance of its directors and officers.

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unpredictable, the results of any such actions may have a material adverse effect on our business, operating results or financial condition.

have assets located outside of Canada, and therefore it may be difficult to enforce judgments obtained by the Company in foreign jurisdictions

by Canadian courts.

Similarly, to the extent that our assets are located outside of Canada, investors may have difficulty collecting

from us any judgments obtained in Canadian courts and predicated on the civil liability provisions of applicable securities legislation.

Furthermore, we may be subject to legal proceedings and judgments in foreign jurisdictions and it may be difficult for U.S.

to effect service of process against the officers of the Company.

have assets located outside of Canada, and therefore it may be difficult to enforce judgments obtained by the Company in foreign

jurisdictions by Canadian courts.

Similarly, to the extent that our assets are located outside of Canada, investors may have

difficulty collecting from us any judgments obtained in Canadian courts and predicated on the civil liability provisions of

applicable securities legislation.

Furthermore, we may be subject to legal proceedings and judgments in foreign jurisdictions and it

may be difficult for U.S.

stockholders to effect service of process against the officers of the Company.

acquisitions could result in potentially dilutive issuances of equity securities, the incurrence of debt, contingent liabilities and/or

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affecting the remittance of dividends, profits, interest, royalties and other payments by the Company to non-resident holders of the

Common Shares, except as discussed below under “ Certain Canadian Federal Income Tax Consequences to Holders of our Common Shares

that are Non-Resident in Canada ”.

Common Shares.

are no limitations under the laws of Canada or in the organizing documents of the Company on the right of foreigners to hold or vote

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trading price of our Common Shares is likely to be volatile.

Upon the consummation of this offering, we will have a relatively small

public float due to the relatively small size of this offering, and the concentrated ownership of our Common Shares among our executive

officers, directors and greater than 5% stockholders.

As a result of our small public float, our Common Shares may be less liquid and

have greater stock price volatility than the common shares of companies with broader public ownership.

stock price could be subject to wide fluctuations in response to a variety of other factors, which include:

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the market price of the Common Shares and diluting their holdings in the Common Shares.

have never paid dividends on our capital stock and we do not anticipate paying any dividends in the foreseeable future.

Equity Issuances and Digital-Asset-Linked Financings May Dilute Existing Shareholders and Affect the Market Price of Our Common Shares

Company has entered into, and may in the future enter into, additional financing arrangements that could result in the issuance of a

substantial number of Common Shares.

During fiscal 2025 and subsequent to year-end, Pineapple Financial Inc.

completed a private placement

of subscription receipts under Project Indigo and granted warrants to Meteora Strategic Capital LLC, each of which may be exchangeable

or exercisable for Common Shares once specified escrow and regulatory conditions are met.

If all such securities are converted or exercised,

the number of outstanding Common Shares would increase materially, resulting in dilution of existing shareholders’ voting and economic

addition, the Company has entered into an Equity Purchase Agreement with White Lion Capital LLC for a discretionary equity line of credit

of up to US $250 million.

Although the facility has not yet been registered with the SEC and no shares have been issued, the Company

may, upon effectiveness of a registration statement and subject to market conditions, sell shares to White Lion Capital from time to

Any such sales could create downward pressure on the market price of the Company’s Common Shares, particularly if large volumes

are issued or perceived to be available for resale.

these arrangements strengthen liquidity and support the Company’s growth initiatives, they also expose shareholders to potential

future dilution and share-price volatility.

The market price of the Company’s Common Shares may fluctuate based on expectations

regarding the timing, scale, or pricing of any future equity issuances under these or similar facilities.

Digital-Asset

Treasury and Market-Value Volatility Could Adversely Affect Our Financial Position and Liquidity

part of its long-term capital strategy, the Company established a Digital Asset Treasury (DAT) that includes holdings of Injective (INJ)

tokens acquired in connection with the Project Indigo private placement and other related transactions.

While these assets are intended

to generate on-chain yield and support future digital-finance initiatives, they expose the Company to risks not typically associated

with traditional financial instruments.

market for digital assets such as INJ is highly volatile and subject to rapid and material fluctuations in value due to regulatory changes,

technology vulnerabilities, network-level disruptions, and shifts in market sentiment.

A significant decline in INJ token prices could

reduce the carrying value of the Company’s digital-asset holdings and collateral base, potentially resulting in impairment charges

or the need to post additional collateral under certain custodial or trading arrangements.

addition, portions of the Company’s INJ assets are held in escrow and staking programs administered by third-party asset managers.

The Company’s access to these assets is therefore limited until escrow-release conditions are satisfied and may also be restricted

by lock-up or yield-program requirements.

Any delays, contractual restrictions, or security incidents affecting these custodial arrangements

could adversely impact the Company’s liquidity and ability to deploy funds for operations or growth initiatives.

management has implemented procedures to monitor counterparty, custody, and market-price risk, there can be no assurance that such measures

will prevent losses or liquidity constraints arising from future market volatility or regulatory developments affecting digital-asset

have never paid dividends on our Common Shares and we do not anticipate paying any dividends in the foreseeable

date, we have not paid any dividends on our outstanding Common Shares and do not currently have a policy with respect to the payment

40 unchanged sentences

Smaller reporting companies may take

advantage of certain reduced disclosure obligations, including, among other things, providing only two years of audited financial statements.

advantage of certain reduced disclosure obligations, including, among other things, providing only two years of audited financial

We will remain a smaller reporting company until the last day of any fiscal year for so long as either:

(i) the market value of our common

shares held by non-affiliates does not equal or exceed $250 million as of the prior June 30th;

or (ii) our annual revenues did not equal

or exceed $100 million during such completed fiscal year.

To the extent we take advantage of such reduced disclosure obligations, it

may also make the comparison of our financial statements with other public companies difficult or impossible.

management team will have broad discretion to use the net proceeds from this offering and its investment of these proceeds may not yield

a favorable return.

They may invest the proceeds of this offering in ways with which investors disagree.

management team will have broad discretion in the application of the net proceeds from this offering and could spend or invest the proceeds

in ways with which our shareholders disagree.

Accordingly, investors will need to rely on our management team’s judgment with respect

to the use of these proceeds.

We intend to use the proceeds from this offering in the manner described in the section entitled “Use

of Proceeds.” The failure by management to apply these funds effectively could negatively affect our ability to operate and grow

our business.

cannot specify with certainty all of the particular uses for the net proceeds to be received upon the closing of this offering.

the amount, allocation and timing of our actual expenditures will depend upon numerous factors.

Accordingly, we will have broad discretion

in using these proceeds.

Until the net proceeds are used, they may be placed in investments that do not produce significant income or

that may lose value.

is not possible to predict the actual number of shares we will sell under the EPA to the Selling Shareholder or the actual gross proceeds

resulting from those sales.

Further, we may not have access to the full amount available under the EPA with the Selling Shareholder.

as of May 10, 2024, we entered into the EPA with the Selling Shareholder, pursuant to which the Selling Shareholder has committed to

purchase up to $15,000,000 of shares of the Company’s Common Shares, subject to certain limitations and conditions set forth in

The Company’s Common Shares that may be issued under the EPA may be sold by us to the Selling Shareholder at our discretion

from time to time.

generally have the right to control the timing and amount of any sales of our Common Shares to the Selling Shareholder under the EPA.

Sales of the Company’s Common Shares, if any, to the Selling Shareholder under the EPA will depend upon market conditions and other

factors to be determined by us.

We may ultimately decide to sell to the Selling Shareholder all, some or none of the Company’s

Common Shares that may be available for us to sell to the Selling Shareholder pursuant to the EPA.

the purchase price per share to be paid by the Selling Shareholder for the Company’s Common Shares that we may elect to sell to

the Selling Shareholder under the EPA, if any, will fluctuate based on the market prices of the Company’s Common Shares prior to

each issuance made pursuant to the EPA, if any, it is not possible for us to predict, as of the date of this prospectus and prior to

any such sales, the number of shares of the Company’s Common Shares that we will sell to the Selling Shareholder under the EPA,

the purchase price per share that the Selling Shareholder will pay for shares purchased from us under the EPA, or the aggregate gross

proceeds that we will receive from those purchases by the Selling Shareholder under the EPA, if any.

although the EPA provides that we may sell up to an aggregate of $15,000,000 of shares of the Company’s Common Shares to the Selling

Shareholder, only 12,400,110 shares of the Company’s Common Shares are being registered for resale under the registration statement

that includes this prospectus.

If we elect to sell to the Selling Shareholder all of the 12,400,110 shares of the Company’s Common

Shares being registered for resale under this prospectus, depending on the market price of the Company’s Common Shares prior to

each advance made pursuant to EPA, the actual gross proceeds from the sale of all such shares may be substantially less than the $15,000,000

available to us under the EPA, which could materially adversely affect our liquidity.

it becomes necessary for us to issue and sell to the Selling Shareholder under the EPA more than the 12,400,110 shares of the Company’s

Common Shares being registered for resale under this prospectus in order to receive aggregate gross proceeds equal to $15,000,000 under

the EPA, we must file with the SEC one or more additional registration statements to register under the Securities Act the resale by

the Selling Shareholder of any such additional shares of the Company’s Common Shares we wish to sell from time to time under the

EPA, which the SEC must declare effective.

Any issuance and sale by us under the EPA of the Company’s Common Shares in addition

to the 12,400,110 shares of the Company’s Common Shares being registered for resale by the Selling Shareholder under the registration

statement that includes this prospectus could cause additional dilution to our stockholders.

are not required or permitted to issue any shares of the Company’s Common Shares under the EPA if such issuance would breach our

obligations under the rules or regulations of NYSE American.

In addition, the Selling Shareholder will not be required to purchase any

shares of the Company’s Common Shares if such sale would result in the Selling Shareholder’s beneficial ownership exceeding

4.99% of the then issued and outstanding shares of the Company’s Common Shares.

Our inability to access a part or all of the amount

available under the EPA, in the absence of any other financing sources, could have a material adverse effect on our business.

(i) the market

value of our Common Shares held by non-affiliates does not equal or exceed $250 million as of the prior June 30th;

annual revenues did not equal or exceed $100 million during such completed fiscal year.

To the extent we take advantage of such

reduced disclosure obligations, it may also make the comparison of our financial statements with other public companies difficult or

we fail to maintain compliance with the continued listing requirements of the NYSE American, the Common Shares may be delisted from the

2 unchanged sentences

is no assurance that we will be able to continue to maintain our compliance with the NYSE American continued listing requirements.

closing price of our Common Shares on June 17, 2024 as reported by the NYSE American was $0.96.

The a company listed on NYSE American

need to have $1.00 minimum share closing price for a period of 30 consecutive trading days in order to meet NYSE American listing standards.

If we fail to do so, our securities would cease to be eligible for trading on the NYSE American and they would likely be traded on the

over-the-counter markets.

As a result, selling our securities could be more difficult because smaller quantities of shares or warrants

would likely be bought and sold, transactions could be delayed, and security analysts’ coverage of us may be reduced.

in the event our securities are delisted, broker-dealers would bear certain regulatory burdens which may discourage broker-dealers from

effecting transactions in the securities and further limit the liquidity of the securities.

These factors could result in lower prices

and larger spreads in the bid and ask prices for the securities.

Such delisting from the NYSE American and continued or further declines

in the share price of the securities could also greatly impair our ability to raise additional necessary capital through equity or debt

financing and could significantly increase the ownership dilution to shareholders caused by our issuing equity in financing or other

transactions.

The closing price of our Common Shares on November 28, 2025 as reported by the NYSE American was $3.44.

listed on NYSE American need to have $1.00 minimum share closing price for a period of 30 consecutive trading days in order to meet

NYSE American listing standards.

If we fail to do so, our securities would cease to be eligible for trading on the NYSE American and

they would likely be traded on the over-the-counter markets.

As a result, selling our securities could be more difficult because

smaller quantities of shares or warrants would likely be bought and sold, transactions could be delayed, and security

analysts’ coverage of us may be reduced.

In addition, in the event our securities are delisted, broker-dealers would bear

certain regulatory burdens which may discourage broker-dealers from effecting transactions in the securities and further limit the

liquidity of the securities.

These factors could result in lower prices and larger spreads in the bid and ask prices for the

Such delisting from the NYSE American and continued or further declines in the share price of the securities could also

greatly impair our ability to raise additional necessary capital through equity or debt financing and could significantly increase

the ownership dilution to shareholders caused by our issuing equity in financing or other transactions.

our Common Shares were to be delisted from the NYSE American, they may become subject to the SEC’s “penny stock” rules.

closing price of our Common Shares on August 31, 2024 as reported by the NYSE American was $0.88.

The a company listed on NYSE American

need to have $1.00 minimum share closing price for a period of 30 consecutive trading days in order to meet NYSE American listing standards.

Delisting from the NYSE American may cause the securities of the Company to become subject to the SEC’s “penny stock”

The SEC generally defines a penny stock as an equity security that has a market price of less than $5.00 per share or an exercise

price of less than $5.00 per share, subject to certain exemptions.

One such exemption is to be registered on a national securities exchange,

such as the NYSE American.

Therefore, if the Common Shares were to be delisted from the NYSE American, the securities of the Company

could become subject to the SEC’s “penny stock” rules.

These rules require, among other things, that any broker engaging

in a purchase or sale of our securities provide its customers with:

(i) a risk disclosure document, (ii) disclosure of market quotations,

if any, (iii) disclosure of the compensation of the broker and its salespersons in the transaction, and (iv) monthly account statements

showing the market values of our securities held in the customer’s accounts.

A broker would be required to provide the bid and

offer quotations and compensation information before effecting the transaction.

This information must be contained on the customer’s

confirmation.

Generally, brokers are less willing to effect transactions in penny stocks due to these additional delivery requirements.

These requirements may make it more difficult for shareholders to purchase or sell the Common Shares of the Company.

Since the broker,

not us, prepares this information, we would not be able to assure that such information is accurate, complete or current.

future sales of Common Shares could cause the market price of our Common Shares to decline.

are contractually obligated to prepare and file with the SEC multiple registration statements providing for the resale of the substantial

majority of the outstanding Common Shares.

Pursuant to the EPA, we may issue and sell up to $15 million of Common Shares to the Selling

The price at which we may issue and sell shares will be 95% of the lowest daily volume weighted average price of the Company’s

Common Shares on the NYSE American during the five (5) trading days immediately preceding the respective put notice date, in each case

as reported by Quotestream or other reputable source designated by the Selling Shareholder (the “Market Price”).

that (a) we issue and sell the full $15 million of Common Shares under the EPA to the Selling Shareholder, (b) no beneficial ownership

limitations, and (c) purchase price for such sales is $1.00 or $3.00 per share, such additional issuances would represent in the aggregate

approximately 15,000,000 or 5,000,000 additional Common Shares, respectively, or approximately 63% or 36% of the total number of Common Shares outstanding as of the date

hereof, after giving effect to such issuance.

If the beneficial ownership limitation is not waived, we may issue approximately 269,480

Common Shares, or approximately 19.99% of the total number of Common Shares outstanding as of the date hereof.

Assuming a (i) Market Price

of $ 0.92, (ii) no beneficial ownership limitations, and (iii) the receipt of stockholder approval to exceed the exchange cap, we may

issue up to 13,169,492 Common Shares, which would reflect approximately 150% of the outstanding shares of our Common Shares as of the

date hereof after giving effect to such issuances.

Market Price of our Common Shares on August 31, 2024, was $0.88.

Assuming this is the Market Price used as a basis for the calculations

for the put notice under the EPA, the price per share for sales to the Selling Shareholder would be $0.84 (95% of the Market Price),

and we would be able to sell 269,480 shares to the Selling Shareholder (with beneficial ownership limit), and receive gross proceeds

Such number of shares would comprise approximately 19.99% of our issued and outstanding Common Shares, which would

result in additional dilution of our shareholders.

while certain of the Selling Holders may experience a positive rate of return based on the current trading price of our Common Shares,

the public stockholders may not experience a similar rate of return on the securities they purchased due to differences in the purchase

prices paid by the public stockholders and the Selling Shareholder and the current trading price of our Common Shares.

The Selling Shareholder

will be able to sell all of their Common Shares for so long as the registration statement of which this prospectus forms a part is available

who buy shares at different times will likely pay different prices.

to the EPA, we will have discretion, subject to market demand, to vary the timing, prices and numbers of shares sold to Selling Shareholder.

If and when we do elect to sell shares of our Common Shares to Selling Shareholder pursuant to the EPA, after Selling Shareholder has

acquired such shares, Selling Shareholder may resell all, some or none of such shares at any time or from time to time in its discretion

and at different prices.

As a result, investors who purchase shares from Selling Shareholder in this offering at different times will

likely pay different prices for those shares and so may experience different levels of dilution, and in some cases substantial dilution,

and different outcomes in their investment results.

Investors may experience a decline in the value of the shares they purchase from

Selling Shareholder in this offering as a result of future sales made by us to Selling Shareholder at prices lower than the prices such

investors paid for their shares in this offering.

In addition, if we sell a substantial number of shares to Selling Shareholder under

the EPA, or if investors expect that we will do so, the actual sales of shares or the mere existence of our arrangement with Selling

Shareholder may make it more difficult for us to sell equity or equity-related securities in the future at a time and at a price that

we might otherwise wish to effect such sales.

UNRESOLVED STAFF COMMENTS

CYBERSECURITY

closing price of our Common Shares on November 28, 2025 as reported by the NYSE American was $3.44.

A company listed on

NYSE American need to have $1.00 minimum share closing price for a period of 30 consecutive trading days in order to meet NYSE

American listing standards.

Delisting from the NYSE American may cause the securities of the Company to become subject to the

SEC’s “penny stock” rules.

The SEC generally defines a penny stock as an equity security that has a market price

of less than $5.00 per share or an exercise price of less than $5.00 per share, subject to certain exemptions.

One such exemption is

to be registered on a national securities exchange, such as the NYSE American.

Therefore, if the Common Shares were to be delisted

from the NYSE American, the securities of the Company could become subject to the SEC’s “penny stock” rules.

rules require, among other things, that any broker engaging in a purchase or sale of our securities provide its customers with:

a risk disclosure document, (ii) disclosure of market quotations, if any, (iii) disclosure of the compensation of the broker and its

salespersons in the transaction, and (iv) monthly account statements showing the market values of our securities held in the

customer’s accounts.

A broker would be required to provide the bid and offer quotations and compensation information before

effecting the transaction.

This information must be contained on the customer’s confirmation.

Generally, brokers are less

willing to effect transactions in penny stocks due to these additional delivery requirements.

These requirements may make it more

difficult for shareholders to purchase or sell the Common Shares of the Company.

Since the broker, not us, prepares this

information, we would not be able to assure that such information is accurate, complete or current.

Future Sales or Issuances of Common Shares, and Digital-Asset-Backed Financings, Could Cause the Market Price of Our Common Shares to

to the fiscal year ended August 31, 2025, the Company entered into several strategic financing and digital-asset-treasury arrangements

designed to strengthen liquidity, diversify capital sources, and advance its digital-finance initiatives.

The principal transactions

are summarized below.

Private Placement

September 4, 2025, the Company closed a US $100 million private placement with certain accredited investors under a Placement Agency

Agreement with D.

Boral Capital LLC.

A total of 24,642,700 subscription receipts were issued at an offering price of $3.80 per subscription receipt, with respect to

certain purchasers, and $4.16 per subscription receipt with respect to certain purchasers, each exchangeable for one Common Share upon satisfaction of escrow-release conditions, including (i) SEC

effectiveness of a Form S-1 resale registration statement, (ii) shareholder approval — which was obtained on October 31, 2025

— and (iii) NYSE American listing confirmation.

consisting of both cash and Injective (INJ) tokens, are held in escrow with Odyssey Transfer & Trust Company and Canary Capital Group

LLC pursuant to a Subscription Receipt Agreement and related Asset Management Agreements.

Upon escrow release, a portion of the funds

will be allocated to working capital and digital-asset-treasury management under the Company’s Injective Digital Asset Treasury

(“DAT”) initiative.

Meteora Warrants

connection with the private placement, the Company granted 1,039,346 five-year warrants to Meteora Strategic Capital LLC, exercisable

at US $3.80 per share.

Full exercise of the Meteora warrants would generate approximately US $3.9 million in gross proceeds and represent about 6 percent

of current outstanding shares (3 percent of post-conversion totals).

Lion Capital LLC Equity Purchase Agreement

September 4, 2025, the Company entered into a Common Stock Purchase Agreement with White Lion Capital LLC, providing a discretionary

Equity Line of Credit (ELOC) of up to US $250 million over a 24-month period.

agreement permits, but does not obligate, the Company to sell newly issued Common Shares to White Lion at prevailing market prices, subject

to SEC registration and customary volume limitations.

As of the date of this filing, no shares have been issued, no proceeds received,

and the agreement has not yet been registered with the SEC.

Accordingly, the facility is not included in the Company’s current

dilution or capital-exposure analysis.

Potential Share Issuances

following table summarizes potential issuances arising from existing equity-linked instruments as of August 31, 2025.

White Lion ELOC is excluded as it remains unregistered and inactive.

Source / Instrument

Max Shares Issuable (approx.)

Assumed Issue Price (US $)

Potential Gross Proceeds (US $ millions)

% of Current O/S (≈ 16 M)

% of Post-Issue Total

Subscription Receipts

Meteora Warrants

Total Potential Issued / Secured

believes these equity-linked financings collectively enhance liquidity and position the Company for long-term growth while maintaining

prudent capital-structure discipline.

The Company will continue to prioritize non-dilutive financing options and intends to activate

the White Lion ELOC only after SEC registration is effective and market conditions are favorable.

Together with the Injective Digital

Asset Treasury program, these initiatives provide a balanced framework for supporting growth and strategic investments while preserving

shareholder value.

Compared sentence by sentence after normalising whitespace, quotation marks, case and digits, so re-formatting and restated figures do not read as changed language. Wording changes appear as one removal and one addition. The current filing and the prior one are authoritative.

What changed 10-K

Item 1A. Risk Factors