Canada: Capital Gains Tax

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Selling Your Business? The Tax Differences Between Selling Shares And Selling Assets For Canadians

The sale of a business, usually operated through a corporation, can be structured as either a share sale or an asset sale, and the two are legally and practically distinct. In a share sale, the vendor sells the corporation’s shares to the purchaser, so that the purchaser acquires control of the corporation’s assets indirectly through share ownership.

RS

Rotfleisch & Samulovitch P.C.

Offshore Investment Fund Property: How Section 94.1 Taxes Canadians On Offshore Fund Income They Never Received And How To File An Objection

If you hold units or shares of an offshore hedge fund, a foreign investment company or any other non-resident fund that reinvests its income instead of paying it out, the CRA may be able to tax you every year on income you never received.

RS

Rotfleisch & Samulovitch P.C.

A Canadian Tax Lawyer’s Complete Guide To Individual Income Tax Returns – T1

Canada’s income tax system is fundamentally based on self-assessment. Individual taxpayers are responsible for reporting their income, claiming applicable deductions and credits, and determining their tax position through the T1 General, formally the T1 Income Tax and Benefit Return.

RS

Rotfleisch & Samulovitch P.C.

Subsection 55(2) Of The Income Tax Act : The Anti-Avoidance Rule, Deliberate Triggering For The CDA, And The Bill C-59 GAAR Overlay

Subsection 55(2) of the Income Tax Act (ITA) is the anti-avoidance rule that stops corporations from using tax-free intercorporate dividends to strip out accrued capital gains that aren’t backed by taxed corporate income.

RS

Rotfleisch & Samulovitch P.C.

What Does A “Gift” Mean For Canadian Income Tax Purposes?

RS

Rotfleisch & Samulovitch P.C.

Guide To Crypto Airdrop Tax In Canada: Airdrops And Token Rewards & How They Are Taxed In Canada

RS

Rotfleisch & Samulovitch P.C.

‘Deemed Disposition’ Of All Your Assets At Death: Tax Planning For Canadian Business Owners With High-Net-Worth Estates

RS

Rotfleisch & Samulovitch P.C.

Guide To The Canadian Tax Treatment Of Halal Mortgages: Halal Mortgages Are Shari'ah-Compliant But Taxable In Canada

RS

Rotfleisch & Samulovitch P.C.

Transfert d’entreprise familiale : quelles règles fiscales faut-il connaître?

BB

BCF Business Law

Foreign Affiliates And Controlled Foreign Affiliates: Canadian Income Tax Guide From A Toronto Tax Lawyer

RS

Rotfleisch & Samulovitch P.C.

Donating Appreciated Publicly Traded Securities To Charity

RS

Rotfleisch & Samulovitch P.C.

Holding Or Moving Cryptocurrency In A Corporation: Learn How CRA’s Taxes Passive Income From Digital Assets

RS

Rotfleisch & Samulovitch P.C.

How CRA Treats $40M In Stolen Bitcoin Cryptocurrency: Lessons From Coinkite Coldcard Hack

RS

Rotfleisch & Samulovitch P.C.

Prediction Markets In Canada: Tax Rules And CIRO Requirements

Canada Commercial

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Devry Smith Frank LLP

Powering Up: Grid Access, Strategic Screening And Canada’s Emerging Data Centre Regimes

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McMillan LLP

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Canada Employment

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Littler - Canada

Simplified Canadian Transfer Pricing Rules

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Millar Kreklewetz

From Duties To Import Bans: The Canada–U.S. Tariff War After The Collapse Of Negotiations

Global International

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Borden Ladner Gervais LLP

The GST/HST New Housing Rebate In 2026: A Complete Guide To Eligibility, Ontario's Enhanced Rebate, And How To Avoid Case Law Traps

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Rotfleisch & Samulovitch P.C.

Guide To Crypto Airdrop Tax In Canada: Airdrops And Token Rewards & How They Are Taxed In Canada

Free tokens are rarely free of tax consequences. Airdrops, staking rewards, yield-farming distributions and DAO compensation all arrive in a crypto wallet without a purchase, which makes them easy to overlook at filing time, and difficult to characterize when they are not overlooked.

RS

Rotfleisch & Samulovitch P.C.

‘Deemed Disposition’ Of All Your Assets At Death: Tax Planning For Canadian Business Owners With High-Net-Worth Estates

Canada does not generally impose a separate inheritance tax on beneficiaries. That does not mean death is tax-free. Under subsection 70(5) of the Income Tax Act, a Canadian taxpayer is generally deemed to dispose of each capital property at fair market value immediately before death, unless a specific rollover or other relieving rule applies.

RS

Rotfleisch & Samulovitch P.C.

Guide To The Canadian Tax Treatment Of Halal Mortgages: Halal Mortgages Are Shari'ah-Compliant But Taxable In Canada

If you are a Muslim homebuyer weighing a halal mortgage against a conventional one, the product that keeps you offside your faith may still put you offside the taxman in ways a conventional mortgage never would.

RS

Rotfleisch & Samulovitch P.C.

The Complete Guide To Crypto-Asset Reporting Framework (CARF) For 2026-27 For Canadian Crypto Traders, Investors, And Accountants—and Enhanced Mandated Data Sharing Of Wallets With CRA

The Canada Revenue Agency’s access to information about cryptocurrency and other crypto-assets is entering a new phase. Canadian taxpayers have always been responsible for identifying, valuing, classifying, and reporting taxable crypto activity, even where an exchange issued no Canadian tax slip, the transaction occurred through a foreign platform, or the assets were never converted into Canadian dollars.

RS

Rotfleisch & Samulovitch P.C.

What Traders And Investors Need To Know About Cryptocurrency Tax Audits In Canada: CRA’s Tax Treatment, Audit Methods, Net-Worth Assessments, And Canadian Taxpayer Rights

RS

Rotfleisch & Samulovitch P.C.

Everything You Need To Know About Crypto Tax Planning Through A Canadian-Controlled Private Corporation (CCPC) In 2026: Incorporation vs. Personal Holding, Expense Deductions, And Integrating With Other Income Sources

RS

Rotfleisch & Samulovitch P.C.

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.

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.

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

RS

Rotfleisch & Samulovitch P.C.

Tax Court Shuts Down Foreign Continuance Loophole: CRA Can Tax A Canadian-Controlled Private Corporation (CCPC): Lessons From Somerset Limited v The King, 2026 TCC 123

RS

Rotfleisch & Samulovitch P.C.

Cryptocurrency Tax Enforcement Measures In The U.K. And Canada, Compared By A Crypto Tax Lawyer

RS

Rotfleisch & Samulovitch P.C.

What Traders And Investors Need To Know About Cryptocurrency Tax Audits In Canada: CRA’s Tax Treatment, Audit Methods, Net-Worth Assessments, And Canadian Taxpayer Rights

The Canada Revenue Agency’s (“CRA”) authority to conduct a cryptocurrency tax audit begins with subsection 231.1(1) of the Income Tax Act. It gives authorized CRA officials broad powers to inspect or examine relevant documents, records, property, processes, and other matters, and to require reasonable assistance and proper oral or written answers.

RS

Rotfleisch & Samulovitch P.C.

Everything You Need To Know About Crypto Tax Planning Through A Canadian-Controlled Private Corporation (CCPC) In 2026: Incorporation vs. Personal Holding, Expense Deductions, And Integrating With Other Income Sources

Savvy crypto investors and traders in Canada often ask the same question: should crypto activity be carried on personally or through a Canadian-controlled private corporation, commonly called a CCPC? In 2026, that question still has no one-size-fits-all answer. The right structure depends on factors such as the type of crypto activity, the level of profit, the need to deduct expenses, whether the taxpayer wants to combine crypto results with other income sources, and more.

RS

Rotfleisch & Samulovitch P.C.

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)

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.

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

As cryptocurrency continues to gain acceptance in commercial transactions, some Canadian employers have started compensating employees using digital assets such as Bitcoin or Ethereum.

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.

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

RS

Rotfleisch & Samulovitch P.C.

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

RS

Rotfleisch & Samulovitch P.C.

Navigating The TOSI Rules: Income Splitting & How To Legally Split Corporate Income With Family

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.

How CRA Treats Cryptocurrency Tax In Divorce And Family Law Settlements In Canada

RS

Rotfleisch & Samulovitch P.C.

Crypto Estate Planning In Canada: CRA Tax Treatment On Death, Wills And Inheritance

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.

The Tale Of Spouses And The Principal Residence Exemption (PRE) Conundrum

OE

O'Sullivan Estate Lawyers LLP

Ontario Farm And Agribusiness Succession Planning: How To Protect Value And Reduce Tax Risk

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Lerners LLP

Ottawa Makes $10-million EOT Exemption Permanent

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Miller Thomson LLP

Navigating The TOSI Rules: Income Splitting & How To Legally Split Corporate Income With Family

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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.

How CRA Treats Cryptocurrency Tax In Divorce And Family Law Settlements In Canada

RS

Rotfleisch & Samulovitch P.C.

Crypto Estate Planning In Canada: CRA Tax Treatment On Death, Wills And Inheritance

RS

Rotfleisch & Samulovitch P.C.

The Inside Scoop On 5 Aggressive Tactics The CRA Is Using In Cryptocurrency Audits

RS

Rotfleisch & Samulovitch P.C.

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Highlighted Content

Selling Your Business? The Tax Differences Between Selling Shares And Selling Assets For Canadians

RS

Rotfleisch & Samulovitch P.C.

Offshore Investment Fund Property: How Section 94.1 Taxes Canadians On Offshore Fund Income They Never Received And How To File An Objection

RS

Rotfleisch & Samulovitch P.C.

A Canadian Tax Lawyer’s Complete Guide To Individual Income Tax Returns – T1

RS

Rotfleisch & Samulovitch P.C.

Subsection 55(2) Of The Income Tax Act : The Anti-Avoidance Rule, Deliberate Triggering For The CDA, And The Bill C-59 GAAR Overlay

RS

Rotfleisch & Samulovitch P.C.

What Does A “Gift” Mean For Canadian Income Tax Purposes?

RS

Rotfleisch & Samulovitch P.C.

Guide To Crypto Airdrop Tax In Canada: Airdrops And Token Rewards & How They Are Taxed In Canada

RS

Rotfleisch & Samulovitch P.C.

‘Deemed Disposition’ Of All Your Assets At Death: Tax Planning For Canadian Business Owners With High-Net-Worth Estates

RS

Rotfleisch & Samulovitch P.C.

Guide To The Canadian Tax Treatment Of Halal Mortgages: Halal Mortgages Are Shari'ah-Compliant But Taxable In Canada

RS

Rotfleisch & Samulovitch P.C.

The Complete Guide To Crypto-Asset Reporting Framework (CARF) For 2026-27 For Canadian Crypto Traders, Investors, And Accountants—and Enhanced Mandated Data Sharing Of Wallets With CRA

RS

Rotfleisch & Samulovitch P.C.

What Traders And Investors Need To Know About Cryptocurrency Tax Audits In Canada: CRA’s Tax Treatment, Audit Methods, Net-Worth Assessments, And Canadian Taxpayer Rights

RS

Rotfleisch & Samulovitch P.C.

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