What changed in this filing

/stocks — the workspaceLOADING

Item 1A. Risk Factors

2024-12-20 compared with 2023-12-14 · 266 added, 9 removed, 601 unchanged (31% of the section changed)

404 unchanged sentences

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

pressure on the global and Canadian markets have caused upward pressure on interest rates impacting mortgage qualification and eligibility.

This pressure has immediately impacted Canadian borrower’s ability to get approved for financing, which in turn has created a decrease

in total loan originations.

There is currently no indication as to when this inflationary pressure will ease or whether that would change

the current environment that has led to our recent growth.

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.

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.

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

29 unchanged sentences

Union, complications involving terrorism and armed conflicts around the world, or other challenges to global trade or travel.

addition, the current outbreak of COVID-19, and any future emergence and spread of similar pathogens, could have a material adverse impact

addition, the past outbreak of COVID-19, and any future emergence and spread of similar pathogens, could have a material adverse impact

on global economic conditions, which may adversely impact:

84 unchanged sentences

be impaired, which could have an adverse impact on our operations and financial condition.

In addition, the COVID-19 pandemic may cause

us to have inadequate access to an available skilled workforce and qualified personnel, which could have an adverse impact on our financial

performance and financial condition.

may be difficult to enforce civil liabilities under Canadian securities laws.

75 unchanged sentences

trust or joint venture that is ultimately controlled by non-Canadians.

Related to Our Securities

investment in our securities carries a high degree of risk and should be considered as a speculative investment.

We have a limited history

of earnings, a limited operating history, have not paid dividends, and are unlikely to pay dividends in the immediate or near future.

The likelihood of our success must be considered in light of the problems, expenses, difficulties, complications and delays frequently

encountered in connection with the establishment of any business.

An investment in our securities may result in the loss of an investor’s

entire investment.

Only potential investors who are experienced in high risk investments and who can afford to lose their entire investment

should consider an investment our securities.

market price of our Common Shares may be highly volatile, and you could lose all or part of your investment.

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:

we achieve our anticipated corporate objectives;

in financial or operational estimates or projections;

of the lock-up agreement or other restrictions on the ability of our stockholders to sell shares after this offering;

economic or political conditions in the United States or elsewhere.

addition, the stock market in general has recently experienced extreme price and volume fluctuations that have often been unrelated or

disproportionate to the operating performance of these companies.

Such rapid and substantial price volatility, including any stock run-up,

may be unrelated to our actual or expected operating performance and financial condition or prospects, making it difficult for prospective

investors to assess the rapidly changing value of our Common Shares.

This volatility may prevent you from being able to sell your Common

Shares at or above the price you paid for them.

If the market price of our Common Shares after this offering does not exceed the offering

price, you may not realize any return on your investment in us and may lose some or all of your investment.

may, in the future, issue additional Common Shares or other securities, which would reduce investors’ percent of ownership and

dilute our share value.

sales or issuances of equity securities could decrease the value of the Common Shares, dilute shareholders’ voting power and reduce

future potential earnings per Common Share.

We may sell additional equity securities in subsequent offerings (including through the sale

of securities convertible into Common Shares) and may issue additional equity securities to finance our operations, acquisitions or other

business projects.

We cannot predict the size of future sales and issuances of equity securities or the effect, if any, that future sales

and issuances of equity securities will have on the market price of the Common Shares.

Sales or issuances of a substantial number of

equity securities, or the perception that such sales could occur, may adversely affect prevailing market prices for the Common Shares.

With any additional sale or issuance of equity securities, investors will suffer dilution of their voting power and may experience dilution

in our earnings per Common Share.

to the terms of our Articles of Incorporation and Canadian securities law, we are not restricted from issuing additional Common Shares

or securities similar to the Common Shares, including any securities that are convertible into or exchangeable for, or that represent

the right to receive, Common Shares.

The market price of the Common Shares could decline as a result of sales of Common Shares, sales

of other securities made after this offering, or as a result of the perception that such sales could occur.

Because our decision to issue

securities in any future offering will depend on market conditions and other factors beyond our control, we cannot predict or estimate

the amount, timing or nature of any future offerings.

Thus, holders of the Common Shares bear the risk of our future offerings reducing

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.

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

of dividends or other distributions.

We do not currently pay dividends and do not intend to pay dividends in the foreseeable future.

Any decision to pay dividends on the Common Shares of the Company will be made by the Board on the basis of the Company’s earnings,

financial requirements and other conditions.

See “Dividend Policy”.

are an “emerging growth company,” and any decision on our part to comply only with certain reduced reporting and disclosure

requirements applicable to emerging growth companies could make our Common Shares less attractive to investors.

are an “emerging growth company,” as defined in Section 2(a) of the Securities Act.

For as long as we continue to be an “emerging

growth company,” we may choose to take advantage of exemptions from various reporting requirements applicable to other public companies

that are not “emerging growth companies,” including, but not limited to, not being required to have our independent registered

public accounting firm audit our internal control over financial reporting under Section 404, reduced disclosure obligations regarding

executive compensation in our periodic reports and exemptions from the requirements of holding a nonbinding advisory vote on executive

compensation and shareholder approval of any golden parachute payments not previously approved.

We could be an “emerging growth

company” until the fifth anniversary of the fiscal year end date following the completion of this offering, however, our status

would change more quickly if we have more than US$1.235 billion in annual revenue, if the market value of our Common Shares held by non-affiliates

equals or exceeds US$700 million as of June 30 of any year, or we issue more than US$1.0 billion of non-convertible debt over a three-year

period before the end of that period.

could find our Common Shares less attractive if we choose to rely on these exemptions.

If some investors find our Common Shares less

attractive as a result of any choices to reduce future disclosure, there may be a less active trading market for our Common Shares and

our share price may be more volatile.

as long as we are an “emerging growth company”, our independent registered public accounting firm will not be required to

attest to the effectiveness of our internal controls over financial reporting pursuant to Section 404.

We could be an “emerging

growth company” until the fifth anniversary of the fiscal year end date following the completion of this offering.

An independent

assessment of the effectiveness of our internal controls could detect problems that our management’s assessment might not.

material weaknesses in our internal controls could lead to financial statement restatements and require us to incur the expense of remediation.

we identify material weaknesses in our internal control over financial reporting, or if we are unable to comply with the requirements

of Section 404 in a timely manner or assert that our internal control over financial reporting is effective, or if our independent registered

public accounting firm is unable to express an opinion as to the effectiveness of our internal control over financial reporting when

required, investors may lose confidence in the accuracy and completeness of our financial reports and the market price of our securities

could be negatively affected, and we could become subject to investigations by the stock exchange on which our securities are listed,

the SEC, or other regulatory authorities, which could require additional financial and management resources.

are a “smaller reporting company” and, even if we no longer qualify as an emerging growth company, we may still be subject

to reduced reporting requirements.

Additionally,

we are a “smaller reporting company” as defined in Item 10(f)(1) of Regulation S-K.

Smaller reporting companies may take

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

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.

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

NYSE American, which would result in a limited trading market for our Common Shares and make obtaining future debt or equity financing

more difficult for the Company.

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.

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

1 unchanged sentence

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