Tax Page

09/01/2026

The CRA Looks for These Real Estate Audit Red Flags. Do Any Apply to You?

Last week, the CRA announced the sentencing of a Vancouver realtor in a tax-evasion case involving a residential property.

It’s a timely reminder that, when it comes to real estate, the CRA may look beyond what appears on a tax return.

Some factors that can attract closer scrutiny include:

• Short holding periods before resale
• Significant renovations or development-like activity
• Frequent property transactions
• Reported income that appears inconsistent with property acquisitions
• MLS listings, photographs or social media that contradict claims about occupancy, personal use or the purpose of the property

None of these factors automatically means a taxpayer will be audited. But individually or together, they can give the CRA reason to look more closely.

Consistency matters.

Your financing, occupancy history, renovation activity, public listings and tax reporting should tell the same story.

Tax advice also doesn’t have to begin after an audit notice arrives. For significant or unusual real-estate transactions, early advice can help identify potential exposure before it becomes a dispute.

Facing a CRA real-estate audit or concerned about the tax implications of a transaction?

📞 416-367-4222 - FREE 10-minute consultation
📩 [email protected]

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08/31/2026

Today, we say a fond farewell - and hopefully, a “see you soon” - to our incredible 2026 summer students: Jessica Gan, Zhixian (Jason) Jin, and Maya Caplan.

Over the past few months, they gained hands-on experience in tax research, client matters, CRA interactions, cryptocurrency tax issues, legal writing, and the day-to-day realities of tax practice.

Looking back on their summer, Jessica especially valued working directly with clients and CRA officers on real tax disputes. For Jason, one of the highlights was seeing his research contribute to real client matters. And for Maya, it was helping anxious clients navigate their tax issues and ease the burden of tax debts.

Their advice to future summer students was simple: ask questions, stay curious, seek out different files and lawyers, and make the most of every opportunity to learn.

Thank you, Jessica, Jason, and Maya, for your hard work, curiosity, and dedication throughout the summer.

We wish you all the very best in the next chapter of your legal careers!

08/19/2026

Are Prediction Market Profits Really Tax-Free in Canada?

Not necessarily.

A Canadian taxpayer could earn C$250,000 on Polymarket, Kalshi or another prediction market** and face very different tax consequences depending on how the activity is characterized.

The CRA has not published specific guidance on the Canadian income-tax treatment of prediction markets. That means existing Canadian tax principles have to be applied to an activity that can resemble gambling, investing, trading, or a combination of all three.

Depending on the facts, profits could potentially be treated as:

• Non-taxable windfalls
• Capital gains
• Fully taxable business income

How you conduct the activity matters.

Occasional recreational participation looks very different from frequent trading involving substantial research, forecasting models, repeated transactions and a systematic effort to generate profits.

There is also an important issue involving losses.

If you take the position that your profits are non-taxable windfalls, that same characterization may mean your losses are not deductible. Conversely, treating losses as business losses may strengthen the argument that your profits should also be taxed as business income.

Using cryptocurrency or stablecoins can add another layer.

Funding prediction-market activity with crypto may create separate Canadian tax consequences on the cryptocurrency transactions themselves, in addition to the tax treatment of the prediction-market activity.

And the way you report your profits is not necessarily the final word. The CRA could later reassess and take a different view of how the activity should have been characterized.

If you trade on Polymarket, Kalshi or another prediction market, keep records of your trading frequency, strategy, transactions, funding, holding periods, and gains or losses. Those records may become important in supporting your tax position if the CRA later takes a different view.

Read our full analysis:
https://taxpage.com/articles-and-tips/betting-on-elections-or-sports-how-the-cra-taxes-prediction-markets-and-are-your-prediction-market-gains-tax-free/

Need guidance on the Canadian tax treatment of prediction-market or cryptocurrency transactions?

📞 416-367-4222 — FREE 10-minute consultation
📩 [[email protected]]

Taxpage.com

All the tax help you need.

08/11/2026

Can the CRA Force Your Accountant to Hand Over Your Tax Files?

Yes, but not always.

A taxpayer may work with both a tax lawyer and an accountant, but that does not automatically mean everything shared with the accountant is protected by solicitor-client privilege.

A recent Federal Court decision, Minister of National Revenue v KPMG Canada LLP, T-139-26, brought this distinction into focus.

The CRA was auditing a group of taxpayers for their 2019 and 2020 taxation years and issued a Requirement for Information directly to KPMG Canada.

KPMG resisted production based on solicitor-client privilege asserted by the taxpayers and provided a privilege log covering more than 900 documents. The taxpayers later produced 90 documents voluntarily, but the dispute continued over the remaining material.

The Federal Court ultimately granted the CRA’s application for a compliance order after finding there was insufficient evidence to establish that the outstanding documents were protected by solicitor-client privilege or another recognized privilege.

The key point is this:

Claiming that a document is privileged does not, by itself, make it privileged.

The nature of the professional relationship, the purpose of the communication and the evidence supporting the privilege claim all matter.

Professional confidentiality and solicitor-client privilege are not necessarily the same thing.

In some circumstances, an accountant’s work may fall within solicitor-client privilege where the accountant is retained by a tax lawyer to assist in providing legal advice and the work is genuinely connected to that advice.

But simply having both a lawyer and accountant involved does not automatically make accounting records privileged.

For taxpayers dealing with CRA audits, voluntary disclosures, unreported income or offshore tax issues, understanding this distinction before sensitive records come under scrutiny can be important.

Read the full analysis in the comments.

Taxpage

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08/10/2026

Please join us in welcoming Andrew (Mihnwan) Son and Lucy (Jingwen) Wei, our 2026/2027 articling students!

Each year, we look forward to welcoming new articling students and supporting them as they take an important step from law school into legal practice.

Andrew is a familiar face at Taxpage, returning after previously spending time with us as a summer student. A 2026 Osgoode Hall Law School graduate, he developed a strong interest in tax law and gained advocacy experience representing clients before the Landlord and Tenant Board through Parkdale Community Legal Services.

Lucy, also a 2026 Osgoode graduate, developed particular interests in consumption tax, trusts and cryptocurrency taxation. Having studied and worked in both China and Canada, she also brings an internationally informed perspective to the firm.

We’re delighted to have Andrew back and to welcome Lucy to the team. We look forward to supporting them throughout what we hope will be a rewarding and successful articling year.

Welcome, Andrew and Lucy!

From all of us at Taxpage.

Taxpage

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08/04/2026

Bitcoin Stolen in a Crypto Hack? Can You Claim a Tax Loss?

Losing Bitcoin to a hack can be financially devastating. Unfortunately, the tax relief available may be far less than the value of the cryptocurrency that disappeared.

A recently reported vulnerability affecting Coldcard hardware wallets has reportedly resulted in substantial Bitcoin losses. For affected Canadians, the questions are immediate:

Can I claim a tax loss? How much can I claim? When can I claim it? What happens if I am reimbursed later?

Consider this example:

You purchased Bitcoin for C$20,000, and it was worth C$60,000 when stolen.

If you held it as a long-term investment and received no compensation, your capital loss would generally be based on your C$20,000 adjusted cost base; not the C$60,000 market value when the theft occurred.

The additional C$40,000 was an unrealized gain that had never been taxed.

At the currently enacted 50% inclusion rate, the allowable capital loss would be C$10,000. That amount may generally be applied against taxable capital gains.

It is not a C$10,000 tax refund, and it generally cannot be deducted against employment income, interest income or other ordinary income.

The result may be different if your cryptocurrency activities amount to carrying on a trading business. In that case, the loss may be treated as a business loss, depending on your trading activity, intention and surrounding circumstances.

Can you claim the loss immediately?

Not necessarily.

If insurance, reimbursement or another form of recovery may be available, the timing and amount of the loss can change.

You cannot claim the full theft loss and later ignore compensation received for the same Bitcoin. A subsequent reimbursement may require you to adjust the amount previously reported or amend your tax return.

Affected taxpayers should immediately preserve:

✅ Purchase and adjusted-cost-base records
✅ Wallet addresses and transaction IDs
✅ Evidence showing when and how the theft was discovered
✅ Police, forensic or incident reports
✅ Communications regarding insurance, reimbursement or recovery

All amounts must also be calculated in Canadian dollars using the appropriate exchange rates for the relevant dates.

A blockchain transaction may prove that the Bitcoin left your wallet. It does not, by itself, establish how much you can claim, when you can claim it or how the CRA will characterize the loss.

If you were affected by the Coldcard incident or another cryptocurrency theft, obtain professional tax advice before filing or amending your return.

Read our full analysis:
https://cryptotaxlawyer.com/how-cra-treats-40m-in-stolen-bitcoin-cryptocurrency-lessons-from-coinkite-coldcard-hack/

Questions about the Canadian tax consequences of stolen cryptocurrency?

📞 416-367-4222 for FREE 10-minute consultation
📩 [email protected]

Taxpage

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07/22/2026

David Rotfleisch Shares Expert Insights in Global Law Experts Q&A

We are pleased to share a recent Q&A featuring David Rotfleisch, Canadian tax lawyer and founding tax lawyer of Tax Page, in collaboration with Global Law Experts (GLE).

During the interview, David discusses Taxpage’s experience helping taxpayers navigate complex Canadian and international tax matters, including:

• Cryptocurrency taxation
• Canada’s departure tax
• Immigration and emigration tax planning
• CRA offshore audits
• Cross-border tax matters

David also shares the example of a taxpayer whose offshore audit continued for approximately 10 years despite the taxpayer having disclosed the foreign assets and filed Form T1135.

The discussion highlights the importance of obtaining experienced legal guidance when dealing with complex tax reporting, relocation, cryptocurrency investments or disputes involving the CRA.

To watch the full interview here: See Comment

Questions about cryptocurrency taxation, departure tax or cross-border tax matters?

📞 416-367-4222 for FREE 10-minute consultation
📩 [email protected]

Taxpage

All the tax help you need.

07/09/2026

Can the CRA Reassess You After Giving You Incorrect Tax Advice?

Yes.

Receiving incorrect tax advice from the CRA does not necessarily prevent a reassessment.

One piece of advice we consistently give taxpayers is simple: don't rely on the CRA's general enquiries line for tax advice.

Recent reports from Canada's Auditor General and the Taxpayers' Ombudsperson reinforce exactly why. The Auditor General found that CRA telephone agents answered only 17% of tested tax questions accurately.

Despite those findings, Canadian taxpayers remain legally responsible for filing accurate tax returns. In most cases, the CRA is not legally bound by incorrect advice provided through its general enquiries line.

If you've been reassessed after relying on incorrect CRA advice, you may still have legal options, including:

1. Applying for taxpayer relief to request the cancellation or waiver of interest and penalties.

2. Filing a Notice of Objection to dispute the reassessment.

3. Challenging gross negligence penalties where appropriate.

If you contact the CRA, keep detailed records of every conversation, including the date, the agent's name or identification number (if provided), and the advice you received.

One important point: General telephone advice from the CRA is not legally binding. If certainty is required, seek independent professional tax advice or determine whether a formal Advance Income Tax Ruling is appropriate.

Read our full analysis:
https://taxpage.com/articles-and-tips/cra-agents-answer-only-17-of-tax-questions-accurately-what-canadian-taxpayers-must-know-about-the-auditor-general-and-ombudsperson-reports/

Need help responding to a CRA reassessment?

📞 416-367-4222 for FREE 10-minute consultation

📧 [email protected]

Taxpage.com

All the tax help you need.

Disclaimer: Posts on this page are for educational purposes only. Not ≠ tax or legal advice.

07/07/2026

Can Canadian Taxpayers Legally Choose Not to Pay Tax?

Recent headlines surrounding King Charles III's voluntary payment of personal income tax have revived a familiar misconception: that paying income tax is optional.

In Canada, it is not.

King Charles recently disclosed that he voluntarily paid £12.9 million in personal income and capital gains tax for the 2024/25 tax year. While the British monarch's tax arrangements arise from the United Kingdom's unique constitutional framework, they do not change the legal obligations of Canadian taxpayers.

Canada's tax system is built on voluntary compliance, not voluntary taxation.

Canadian taxpayers are legally required to report income, file tax returns, and pay taxes owing under the Income Tax Act. Courts have consistently rejected arguments that paying income tax is a matter of personal choice.

Acting on misinformation can result in serious consequences, including:

✅ Reassessments and interest.

✅ Gross negligence penalties.

✅ In cases of intentional tax evasion, criminal prosecution, substantial fines, and imprisonment.

The key takeaway: The King's tax disclosure is an interesting constitutional development in the United Kingdom, but it has no effect on the legal obligations of Canadian taxpayers.

To read our full analysis: See Comment

Have questions about your Canadian tax obligations?

📞 416-367-4222 - FREE 10-minute consultation

📧 [email protected]

Taxpage

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#

07/02/2026

Think your home listing is just marketing? The CRA may see it very differently.

If you're buying, renovating, or selling residential property, what you say about it publicly could matter more than you think.

The CRA is increasingly reviewing MLS listings and other third-party information when assessing real estate transactions. Details describing renovations, investment potential, or resale value may be considered alongside ownership history and other evidence when evaluating a taxpayer's intentions.

Here are three important things every homeowner, renovator, and real estate investor should know:

1. 🏡 Your property listing could become part of a CRA audit.

MLS descriptions and listing history may be reviewed when determining whether a property was held for personal use, investment, or resale.

2. ⚖️ You don't have to be a developer to face builder-related GST/HST issues.

Substantial renovations, repeated property transactions, or buying with the intention of resale may expose taxpayers to builder classification under the Excise Tax Act.

3. 💰 The financial consequences can be significant.

Builder classification may trigger GST/HST based on the fair market value of a property. In some situations, the self-supply rules can create GST/HST liability even where no conventional sale has taken place.

Tax tips:

• Keep records that clearly support your intended use of the property.

• Consider your GST/HST obligations before buying, renovating, or selling.

• Seek experienced tax advice early if there's any uncertainty about your tax position.

Read our full analysis here:
https://taxlawcanada.com/cra-real-estate-tax-audits-using-mls-data-builder-risk-gst-hst-exposure-audit-defence-strategies-in-canada/

Need help responding to a CRA real estate tax audit?

📞 416-367-4222 | FREE 10-minute consultation

📧 [email protected]

Taxpage.com

All the tax help you need.