Canada: Income Tax

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Tax law and international tax law thought leadership, articles, podcasts, videos and webinars from expert sources across the legal world. Explore insights covering topics such as capital gains tax, corporate tax, income tax, inheritance tax, national insurance, property taxes, sales taxes, VAT, GST, tax authorities, transfer pricing and withholding tax.

Canadian Tax Treatment Of Prediction Market Gains And Losses: Polymarket, Kalshi, Event Contracts, And Other Predictive Markets

Prediction markets have emerged as one of the fastest-growing areas of online speculation, forecasting, and information-based trading.

RS

Rotfleisch & Samulovitch P.C.

When The CRA Recharacterizes Capital Gains As Business Income: Happy Valley Farms, Stewart V. Canada, And The Legal Framework Governing CRA Tax Audits And Reassessments

Canadian taxpayers—particularly entrepreneurs, real estate investors, and high-net-worth individuals—face significant risk during a CRA tax audit where capital gains may be recharacterized as fully taxable business income, often resulting in a costly CRA tax reassessment.

RS

Rotfleisch & Samulovitch P.C.

How To Sell Your Family Business To Your Children Using Bill C-59 ‘Intergenerational Business Transfer Tax Rules’ Of The Income Tax Act (ITA)

For too long, Canadian tax law penalized business owners who wanted to keep their life’s work in the family. A sale to a stranger entitled the vendor to the lifetime capital gains exemption (LCGE) — currently $1,302,938 for 2026, indexed annually — sheltering over a million dollars of gain from tax.

RS

Rotfleisch & Samulovitch P.C.

The Clear Line Between CRA’s Tax Audit Vs. A Criminal Tax Investigation: Why R V Jarvis Is The Most Important Tax Case For Canadian Taxpayers

The Supreme Court of Canada’s decision in R v Jarvis, 2002 SCC 73, remains the leading authority in Canadian tax law on the boundary between a civil tax audit and a criminal tax investigation. For any Canadian taxpayer facing aggressive CRA scrutiny, understanding the Jarvis framework is not optional — it is essential.

RS

Rotfleisch & Samulovitch P.C.

Paying Employees In Cryptocurrency In Canada: Tax, Payroll Deductions And Considerations

RS

Rotfleisch & Samulovitch P.C.

Stewart v. Canada: Canadian Tax Lawyer Explains Why Supreme Court Of Canada (SCC) Changed ‘Source Of Income Test’ To Include Legitimate Business Losses, Unsuccessful Ventures

RS

Rotfleisch & Samulovitch P.C.

Canadian Influencer Tax Guide: CRA Audit Risks, GST/HST Rules, Cryptocurrency Income, Foreign Reporting, And Tax Planning Strategies

RS

Rotfleisch & Samulovitch P.C.

Estate And Tax Planning For Cross-Border Couples: TFSAs And The IRS

DW

Dickinson Wright PLLC

How The Principal Residence Tax Exemption Works In Canada: Eligibility Requirements, Property Flipping Rules, And Common CRA Tax Traps

RS

Rotfleisch & Samulovitch P.C.

Foreign Pension Income Taxation – A Canadian Tax Lawyer Analysis

RS

Rotfleisch & Samulovitch P.C.

Capital Gains Or Deemed Dividend? Are Your Canadian Family Business Clients Ready For The New IBT Rules?

MT

Miller Thomson LLP

When Can My Charity Issue A Tax Receipt For A Gift Of Private Company Shares?

MT

Miller Thomson LLP

Canada’s Tax Act Is Too Complex: Complaints About CRA Rise 27% Despite Recent Automated Tax Filing, Call Centre Failures, Processing Delays, Poor Communication

RS

Rotfleisch & Samulovitch P.C.

FIFA World Cup 2026 And Canadian Tax: What Short-Term Renters, Businesses, And Bettors Need To Know

RS

Rotfleisch & Samulovitch P.C.

Duty To Inquire About Disabilities: Key Lessons From A Recent Ontario Human Rights Decision

Canada Employment

F

Fasken

49% Of Canadian Visitor Visas Get Refused — Here's Why (And What To Do) (Video)

Canada Immigration

Gs

Green and Spiegel

Cyber Criminals Love Your Deals: How Hidden Cyber Risk Can Blow Up Your M&A (And What To Do About It)

MT

Miller Thomson LLP

Five Questions Every Organization Should Ask Before Conducting A Workplace Investigation

Canada Employment

MT

McCarthy Tétrault LLP

Why Tax Lawyers Have A Secret Weapon Against The CRA & Accountants Don’t: Solicitor-Client Privilege And The Limits Of CRA Audit Powers In Minister Of National Revenue v. KPMG Canada LLP

RS

Rotfleisch & Samulovitch P.C.

Stewart v. Canada: Canadian Tax Lawyer Explains Why Supreme Court Of Canada (SCC) Changed ‘Source Of Income Test’ To Include Legitimate Business Losses, Unsuccessful Ventures

The Supreme Court of Canada’s decision in Stewart v Canada, 2002 SCC 46, represents a foundational shift in Canadian tax law concerning what constitutes a “source of income” under the Income Tax Act.

RS

Rotfleisch & Samulovitch P.C.

Canadian Influencer Tax Guide: CRA Audit Risks, GST/HST Rules, Cryptocurrency Income, Foreign Reporting, And Tax Planning Strategies

The creator economy has fundamentally changed how Canadians earn income. YouTubers, Instagram influencers, TikTok personalities, Twitch streamers, podcasters, affiliate marketers, bloggers, online educators, subscription-based performers, and other digital entrepreneurs now generate substantial revenues through online platforms.

RS

Rotfleisch & Samulovitch P.C.

A Complete Guide To The Canada Greener Homes Affordability Program (CGHAP): Tax Implications For Homeowners, Landlords, And Renters

Green retrofits come with real tax consequences. Understanding how the CRA treats CGHAP grants, rental property deductions, ACB adjustments, principal residence exemption interactions, Class 43.1 eligibility, and Quebec provincial tax obligations is essential before you apply.

RS

Rotfleisch & Samulovitch P.C.

When Can Your Crypto Losses Become Tax Deductions? A Canadian Tax Lawyer On Capital Losses vs Business Losses

Crypto losses are not all deductible in the same way. In Canada, the core question is not simply whether a taxpayer lost money on Bitcoin, Ether, Tao or another token.

RS

Rotfleisch & Samulovitch P.C.

Canada Trustco Mortgage Co. v. Canada: The Supreme Court's Foundational GAAR Decision And Its Three-Step Test

RS

Rotfleisch & Samulovitch P.C.

Qureshi v. The King -Pre-Construction Condominium Flipping, Principal Residence Claims, And GST Builder Liability – Tax Court Rejects Taxpayer’s Attempt To Treat $456,000 Profit As Tax-Free

RS

Rotfleisch & Samulovitch P.C.

Why Interest On Foreign Tax Arrears Is Not Deductible: Canadian Tax Lawyer Explains Tax Court Decision In Bank Of Montreal v. The King, Paragraph 18(1)(a)

RS

Rotfleisch & Samulovitch P.C.

CRA Net Worth Audit Lawyer Canada: How Taxpage.com Successfully Argued Tax Court Of Canada Appeal, Reducing Client’s CRA Tax Reassessment By $400,000+ And Eliminating Gross Negligence Penalties

RS

Rotfleisch & Samulovitch P.C.

The Complete Guide To The New Canada Groceries And Essentials Benefit (CGEB): Eligibility, Payment Dates, CRA Rules, And Taxpayer Rights

RS

Rotfleisch & Samulovitch P.C.

Is A Ransom Payment For Kidnapped Executives Tax-Deductible In Canada? A Canadian Crypto Tax Lawyer's Analysis

RS

Rotfleisch & Samulovitch P.C.

CRA Rejects Unreasonable Expenses For Commissioned Employees, Despite Having Filled Out Form T2200

RS

Rotfleisch & Samulovitch P.C.

France's Crypto Kidnapping Surge Exposes A Deeper Risk: What Canadian Crypto Investors Should Know About Tax Data Exposure And CRA Disclosure

RS

Rotfleisch & Samulovitch P.C.

Learn Why The Tax Court Denied $118,000 In Employment Expense Deductions And The Record-keeping Lessons From Chennenkunnath v. The King

RS

Rotfleisch & Samulovitch P.C.

When The IRS Charges Rappers With Tax Evasion In The United States: What Celebrities And High-Income Earners Need To Know

RS

Rotfleisch & Samulovitch P.C.

A Complete Guide To The Canada Greener Homes Affordability Program (CGHAP): Tax Implications For Homeowners, Landlords, And Renters

Green retrofits come with real tax consequences. Understanding how the CRA treats CGHAP grants, rental property deductions, ACB adjustments, principal residence exemption interactions, Class 43.1 eligibility, and Quebec provincial tax obligations is essential before you apply.

RS

Rotfleisch & Samulovitch P.C.

When Can Your Crypto Losses Become Tax Deductions? A Canadian Tax Lawyer On Capital Losses vs Business Losses

Crypto losses are not all deductible in the same way. In Canada, the core question is not simply whether a taxpayer lost money on Bitcoin, Ether, Tao or another token.

RS

Rotfleisch & Samulovitch P.C.

Canada Trustco Mortgage Co. v. Canada: The Supreme Court's Foundational GAAR Decision And Its Three-Step Test

How the Supreme Court of Canada’s unified textual, contextual and purposive approach in Canada Trustco continues to govern every general anti-avoidance rule assessment issued by the CRA.

RS

Rotfleisch & Samulovitch P.C.

CRA Agents Answer Only 17% Of Tax Questions Accurately: What Canadian Taxpayers Must Know About The Auditor General And Ombudsperson Reports

The government’s own Auditor General has confirmed it: if you call the CRA for tax advice, there is an 83% chance the answer will be wrong.

RS

Rotfleisch & Samulovitch P.C.

When The IRS Charges Rappers With Tax Evasion In The United States: What Celebrities And High-Income Earners Need To Know

RS

Rotfleisch & Samulovitch P.C.

CRA Agents Answer Only 17% Of Tax Questions Accurately: What Canadian Taxpayers Must Know About The Auditor General And Ombudsperson Reports

The government’s own Auditor General has confirmed it: if you call the CRA for tax advice, there is an 83% chance the answer will be wrong.

RS

Rotfleisch & Samulovitch P.C.

King Charles Taxation And Canadian Comparisons: Voluntary Compliance, Crown Privilege, And Tax Transparency

In a development described as historically unprecedented, King Charles III has announced that he will publicly disclose the total amount of personal income tax he voluntarily pays to the British government, with the figure to be published as part of the annual Royal Household finances report.

RS

Rotfleisch & Samulovitch P.C.

CRA Disability Tax Credit: How Type 1 Diabetics Can Secure Retroactive Refunds

For years, Canadians living with Type 1 diabetes faced an uphill battle to obtain the federal Disability Tax Credit (DTC) — a struggle defined by shifting CRA administrative policies, inconsistent application of the Income Tax Act, and mass denials that caused profound financial hardship.

RS

Rotfleisch & Samulovitch P.C.

Why Tax Lawyers Have A Secret Weapon Against The CRA & Accountants Don’t: Solicitor-Client Privilege And The Limits Of CRA Audit Powers In Minister Of National Revenue v. KPMG Canada LLP

The Federal Court’s June 12, 2026 decision in Minister of National Revenue v KPMG Canada LLP, T-139-26, is a significant ruling on the limits of privilege assertions by third-party tax advisors in the context of CRA audits.

RS

Rotfleisch & Samulovitch P.C.

CRA Using AI To Spearhead Crypto Tax Audits In 2026: How To Use The Voluntary Disclosures Program (VDP) To Disclose Unreported Crypto Profits

RS

Rotfleisch & Samulovitch P.C.

The OnlyFans Audit: Why A Canadian Tax Lawyer Warns Creators That The CRA Is Watching (For Income Tax Due)

RS

Rotfleisch & Samulovitch P.C.

Restrictive Covenants In Business Sales Or Share Sales: How To Navigate The Default Rule, Plus Statutory Relief From CRA

RS

Rotfleisch & Samulovitch P.C.

Toronto’s Vacant Home Tax: A Complete Guide To Tax Exemptions, Tax Appeals, And Tax Compliance For Toronto Property Owners

RS

Rotfleisch & Samulovitch P.C.

How Severance Pay Is Taxed In Canada: Guidance From A Canadian Tax Lawyer

RS

Rotfleisch & Samulovitch P.C.

Are Poker Winnings Now Taxable In Canada? A Canadian Tax-Lawyer Analyses Of 4 Tax Court Of Canada Recent Poker Decisions

RS

Rotfleisch & Samulovitch P.C.

The Application Of Alternative Minimum Tax In The Year Of Death

GR

Gardiner Roberts LLP

Tax Treatment Of Employment Settlements In Canada: What Employees And Employers Need To Know Before Signing A Settlement Agreement

Canada Employment

RS

Rotfleisch & Samulovitch P.C.

Business Sale: Tax Strategies To Maximize Your Tax Savings

BB

BCF Business Law

Unreasonable Business Expenses In Canada: When The CRA Can Deny Your Tax Deduction Under Section 67 Of The Income Tax Act

RS

Rotfleisch & Samulovitch P.C.

Why Tax Lawyers Have A Secret Weapon Against The CRA & Accountants Don’t: Solicitor-Client Privilege And The Limits Of CRA Audit Powers In Minister Of National Revenue v. KPMG Canada LLP

RS

Rotfleisch & Samulovitch P.C.

CRA Using AI To Spearhead Crypto Tax Audits In 2026: How To Use The Voluntary Disclosures Program (VDP) To Disclose Unreported Crypto Profits

RS

Rotfleisch & Samulovitch P.C.

The OnlyFans Audit: Why A Canadian Tax Lawyer Warns Creators That The CRA Is Watching (For Income Tax Due)

RS

Rotfleisch & Samulovitch P.C.

Restrictive Covenants In Business Sales Or Share Sales: How To Navigate The Default Rule, Plus Statutory Relief From CRA

RS

Rotfleisch & Samulovitch P.C.

Toronto’s Vacant Home Tax: A Complete Guide To Tax Exemptions, Tax Appeals, And Tax Compliance For Toronto Property Owners

RS

Rotfleisch & Samulovitch P.C.

See more

Highlighted Content

Canadian Tax Treatment Of Prediction Market Gains And Losses: Polymarket, Kalshi, Event Contracts, And Other Predictive Markets

RS

Rotfleisch & Samulovitch P.C.

When The CRA Recharacterizes Capital Gains As Business Income: Happy Valley Farms, Stewart V. Canada, And The Legal Framework Governing CRA Tax Audits And Reassessments

RS

Rotfleisch & Samulovitch P.C.

How To Sell Your Family Business To Your Children Using Bill C-59 ‘Intergenerational Business Transfer Tax Rules’ Of The Income Tax Act (ITA)

RS

Rotfleisch & Samulovitch P.C.

The Clear Line Between CRA’s Tax Audit Vs. A Criminal Tax Investigation: Why R V Jarvis Is The Most Important Tax Case For Canadian Taxpayers

RS

Rotfleisch & Samulovitch P.C.

Paying Employees In Cryptocurrency In Canada: Tax, Payroll Deductions And Considerations

RS

Rotfleisch & Samulovitch P.C.

Stewart v. Canada: Canadian Tax Lawyer Explains Why Supreme Court Of Canada (SCC) Changed ‘Source Of Income Test’ To Include Legitimate Business Losses, Unsuccessful Ventures

RS

Rotfleisch & Samulovitch P.C.

Canadian Influencer Tax Guide: CRA Audit Risks, GST/HST Rules, Cryptocurrency Income, Foreign Reporting, And Tax Planning Strategies

RS

Rotfleisch & Samulovitch P.C.

A Complete Guide To The Canada Greener Homes Affordability Program (CGHAP): Tax Implications For Homeowners, Landlords, And Renters

RS

Rotfleisch & Samulovitch P.C.

When Can Your Crypto Losses Become Tax Deductions? A Canadian Tax Lawyer On Capital Losses vs Business Losses

RS

Rotfleisch & Samulovitch P.C.

Canada Trustco Mortgage Co. v. Canada: The Supreme Court's Foundational GAAR Decision And Its Three-Step Test

RS

Rotfleisch & Samulovitch P.C.

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