Canada: Capital Gains 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.

When Can Businesses Deduct Interest Payments? A Primer From A Canadian Tax Lawyer

The Income Tax Act has rules that allow the deduction of interest in specific situations. Paragraph 20(1)(c) allows interest deduction for borrowed money used to generate business income or property income.

RS

Rotfleisch & Samulovitch P.C.

When Full Business Income Tax, Other Than Capital Gains Tax, Is Payable If Business Activities Are Based On A "Secondary Intention" Tax Law Doctrine In An "Adventure In The Nature Of Trade" – Guidance From A Canadian Tax Lawyer

The tax treatment of income in Canada depends on its classification, making it essential for taxpayers to understand the nature of the income they earn in order to file tax returns accurately and engage in effective tax planning.

RS

Rotfleisch & Samulovitch P.C.

How The Income Tax Act Treats Settlements And Damage Awards For Wrongful Dismissals

The general principle under the Income Tax Act (the "Tax Act") is that for an amount to be considered income, it must belong to a source in section 3.

RS

Rotfleisch & Samulovitch P.C.

How CRA Conducts Net Worth Audits And Enforces Gross Negligence Penalties Against Canadian Taxpayers: Lessons From Mann v. The King And Other Cases

In Mann v. The King, 2023 TCC 151, the Tax Court of Canada reaffirmed the Canada Revenue Agency's (CRA) authority to use the net worth method under subsection 152(7) of the Income Tax Act when a taxpayer fails to keep adequate books and records.

RS

Rotfleisch & Samulovitch P.C.

The GST/HST Implications Of Changing The Use Of Personal Property – How Subsections 199(3), 200(2), And 200(3) Interact

RS

Rotfleisch & Samulovitch P.C.

A Canadian Tax Lawyer's Guide To S.51 Rollovers: What And How Shareholders Can Convert Equity Into New Shares Without Capital Gains

RS

Rotfleisch & Samulovitch P.C.

What Estate Tax Liabilities Do Advisors And Clients Need To Stay Aware Of ?

RA

Robins Appleby LLP

A Canadian Tax Lawyer's Case Commentary On Magren Holdings Ltd. v Canada, 2024 FCA 202: The Application Of General Anti-Avoidance Rule (GAAR) On Capital Dividends

RS

Rotfleisch & Samulovitch P.C.

Argentine President Milei Eyes Tax Reform To Flag Hidden U.S. Dollars, With Implications For Canada-Argentina Cross-Border Tax Planning

RS

Rotfleisch & Samulovitch P.C.

A Canadian Tax Lawyer's Updated Guide On Non-Resident Trusts In Canada

RS

Rotfleisch & Samulovitch P.C.

Tax Strategy, Corporate Structure, And Governance: A Synergy Rich In Possibilities

Canada Commercial

L,

Langlois Lawyers, LLP

The One Simple Question All Advisors Must Ask To Save Their Clients From An IRS Nightmare (And Save Them A Call To Their Malpractice Carrier).

MP

Moodys Private Client Law LLP

The Unexpected Role Of Tariffs In Estate Planning

CW

Clark Wilson LLP

From Duty To Liability: The Evolution Of Trustee Responsibility In Ontario Courts

LL

Lerners LLP

How CRA Conducts Net Worth Audits And Enforces Gross Negligence Penalties Against Canadian Taxpayers: Lessons From Mann v. The King And Other Cases

RS

Rotfleisch & Samulovitch P.C.

A Canadian Tax Lawyer's Update On Voluntary Disclosure: Créations Guimel Inc. v. Canada (National Revenue), 2025 FC 814 – Reviewing CRA's Duty Of Procedural Fairness In VDP In Applications

RS

Rotfleisch & Samulovitch P.C.

Conflit d'intérêts dans l'administration d'une succession : ce que l'affaire Virdi Estate (Re) enseigne aux exécuteurs testamentaires

Canada Litigation

MT

Miller Thomson LLP

Powering The Future: Canada's Leadership In Nuclear Energy & Small Modular Reactors

MA

MLT Aikins LLP

What Happens If An Employee's Work Permit Expires?

Canada Employment

TM

Taylor McCaffrey

A Canadian Tax Lawyer's Guide To S.51 Rollovers: What And How Shareholders Can Convert Equity Into New Shares Without Capital Gains

S.51 rollovers are one of the many tax-free rollovers the Income Tax Act provides taxpayers. A s.51 rollover allows a taxpayer to convert debt or shares in a corporation to new shares of that corporation on a tax-free basis.

RS

Rotfleisch & Samulovitch P.C.

Canada Revenue Agency Tightens Oversight On Cryptocurrency Transactions: What You Need To Know Now

In recent years, the explosive growth of cryptocurrency has attracted the attention of investors, entrepreneurs—and now, tax authorities.

RS

Rotfleisch & Samulovitch P.C.

Beyond Succession: How Employee Ownership Trusts Are Reshaping Canadian Business Exits (Podcast)

What if the best buyer for your business is already working for you? In this episode of Beyond Succession, host Leah Tolton is joined by Bennett Jones partner Wes Novotny...

Canada Commercial

BJ

Bennett Jones LLP

Share Redemption And Share Retraction: Tax Treatment By CRA—plus They Are Useful Tax Planning Tools

Corporate structures in Canada often involve various strategies for managing share ownership, capital returns, and shareholder interests.

RS

Rotfleisch & Samulovitch P.C.

The Pontiff's US Tax Dilemma: Should You, Like Pope Leo XIV, Consider Renouncing Your US Citizenship?

MP

Moodys Private Client Law LLP

Clauses d'indexation sur les bénéfices futurs dans le cadre de fusions et acquisitions de sociétés fermées : Négociation, rédaction et stratégie

Canada Commercial

FF

Fasken (French)

Should Founders Incorporate Their Startups In The United States Or Canada?

Canada Commercial

OH

Osler, Hoskin & Harcourt LLP

Crypto Transactions: Capital Gains Or Business Income? What You Need To Know

Canada Technology

DS

Devry Smith Frank LLP

Federal Election 2025 Tax Implications

MR

McLennan Ross LLP

Probate Planning In BC: Is The Juice Worth The Squeeze?

BC

Boughton Law Corporation

Navigating Cross-Border Tax Challenges

RA

Robins Appleby LLP

Red Flags & Trust Issues: Top 5 Pitfalls In Trusts

MR

McLennan Ross LLP

What's The Limitation On Losses Of Shares Held As Capital Property For Individuals And Corporations? Canadian Tax Lawyer Explains

RS

Rotfleisch & Samulovitch P.C.

House-Flippers Beware: You Are Not Eligible For GST/HST New Housing Rebates – Ram V HMK, 2025 TCC 49

RS

Rotfleisch & Samulovitch P.C.

Canada Revenue Agency Tightens Oversight On Cryptocurrency Transactions: What You Need To Know Now

In recent years, the explosive growth of cryptocurrency has attracted the attention of investors, entrepreneurs—and now, tax authorities.

RS

Rotfleisch & Samulovitch P.C.

Red Flags & Trust Issues: Top 5 Pitfalls In Trusts

Trusts are powerful estate and tax planning tools but they must be carefully structured and properly maintained in order to be effective.

MR

McLennan Ross LLP

What's The Limitation On Losses Of Shares Held As Capital Property For Individuals And Corporations? Canadian Tax Lawyer Explains

Subsection 112(3) of the Income Tax Act is a stop-loss rule that limits losses from the disposition of shares held as capital property.

RS

Rotfleisch & Samulovitch P.C.

House-Flippers Beware: You Are Not Eligible For GST/HST New Housing Rebates – Ram V HMK, 2025 TCC 49

In March 2025, the Tax Court of Canada delivered the judgment on Aneeta Ram v His Majesty the King, 2025 TCC 49, dismissing the appeal by the self-represented litigant Aneeta Ram against the CRA regarding the denial of her claim for the GST/HST new housing rebates.

RS

Rotfleisch & Samulovitch P.C.

April 15 Tax & Private Wealth Group Key Takeaways

WL

World Law Group

Canada's Federal Election 2025 — A Tale Of Two Tax Policies

With the Canadian federal election just under two weeks away, the two major parties leading the current polls, the Liberals (led by Mark Carney) and the Conservatives (led by Pierre Poilievre)...

M

Mintz

Are Pre-Closing Tax Indemnities Reportable Transactions?

The updated mandatory disclosure rules in the Income Tax Act (Canada) (the "ITA") were enacted in June 2023. In general, they are made up of the reporting requirements pertaining to reportable transactions...

MT

Miller Thomson LLP

Legal Pulse - Spring 2025

Parties contemplating the formation of a limited partnership in Ontario should consider the implications of a recent Ontario Superior Court of Justice (ONSC) decision...

Canada Strategy

RA

Robins Appleby LLP

$10M Capital Gains Exemption For Worker Co-Op Sales: A New Succession Option Under Draft Tax Rules

How Canada's 2024 Budget and draft legislation open the door to employee-led business transitions through worker cooperatives.

MT

Miller Thomson LLP

Quebec Budget 2025-26: Important Changes To Quebec Flow-Through Share Regime And Refundable Tax Credit Regime For Mining And Other Resources

BJ

Bennett Jones LLP

Law Change Relating To Trusts Owning Residential Property

DG

De Grandpré Chait

New Guidance From The CRA: Transactions Subject To The GAAR

MT

Miller Thomson LLP

La Cour canadienne de l'impôt radie des hypothèses incohérentes et des nouvelles pénalités dans les procédures du Ministre

MT

McCarthy Tétrault LLP

How Are Limited Partnerships Taxed In Canada? Advantages And Drawbacks From A Canadian Tax Lawyer

RS

Rotfleisch & Samulovitch P.C.

Crypto Tax Trap: Are The Tax Advantages Of A Charitable Remainder Trust Worth It For Canadian Cryptocurrency Investors?

RS

Rotfleisch & Samulovitch P.C.

Règle fédérale sur les reventes précipitées de biens : voici les points à retenir

MT

Miller Thomson LLP

Nouvelles Directives De L'ARC : Opérations Assujetties À La DGAE

MT

Miller Thomson LLP

Exchangeable Share Structures In Cross-Border M&A: What U.S. Buyers Of A Canadian Target Should Know

Canada Commercial

F

Fasken

Theft Of CAD$1.5 Billion Of Ethereum: How CRA Treats Stolen Property Tax-Wise; Plus, Tax Implications For Crypto Exchanges In Canada

RS

Rotfleisch & Samulovitch P.C.

How To Leverage The Tax Benefits Of Canadian-Controlled Private Corporation (CCPC) Structure For Emerging, High-Growth Companies

RS

Rotfleisch & Samulovitch P.C.

Collecte de renseignements par l'ARC : de nouvelles règles attendues en 2025

MT

Miller Thomson LLP

Dix causes dignes de mention en matière d'impôt sur le revenu au Canada en 2024

MT

McCarthy Tétrault LLP

A Lasting Legacy For Your Community

OE

O'Sullivan Estate Lawyers LLP

Using A Trust In Your Estate Plan

OE

O'Sullivan Estate Lawyers LLP

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Highlighted Content

When Can Businesses Deduct Interest Payments? A Primer From A Canadian Tax Lawyer

RS

Rotfleisch & Samulovitch P.C.

When Full Business Income Tax, Other Than Capital Gains Tax, Is Payable If Business Activities Are Based On A "Secondary Intention" Tax Law Doctrine In An "Adventure In The Nature Of Trade" – Guidance From A Canadian Tax Lawyer

RS

Rotfleisch & Samulovitch P.C.

How The Income Tax Act Treats Settlements And Damage Awards For Wrongful Dismissals

RS

Rotfleisch & Samulovitch P.C.

How CRA Conducts Net Worth Audits And Enforces Gross Negligence Penalties Against Canadian Taxpayers: Lessons From Mann v. The King And Other Cases

RS

Rotfleisch & Samulovitch P.C.

The GST/HST Implications Of Changing The Use Of Personal Property – How Subsections 199(3), 200(2), And 200(3) Interact

RS

Rotfleisch & Samulovitch P.C.

A Canadian Tax Lawyer's Guide To S.51 Rollovers: What And How Shareholders Can Convert Equity Into New Shares Without Capital Gains

RS

Rotfleisch & Samulovitch P.C.

Canada Revenue Agency Tightens Oversight On Cryptocurrency Transactions: What You Need To Know Now

RS

Rotfleisch & Samulovitch P.C.

How To Leverage The Tax Benefits Of Canadian-Controlled Private Corporation (CCPC) Structure For Emerging, High-Growth Companies

RS

Rotfleisch & Samulovitch P.C.

2024 Tax Alert: CRA Implements Capital Gains Tax Increase Despite Stalled Legislation – The Unique Tax Challenges For Employee Stock Options & Payroll Tax

RS

Rotfleisch & Samulovitch P.C.

Case Study: Canadian Crypto-Tax Lawyers Save Bitcoin Millionaire From Criminal Prosecution For Tax Evasion

RS

Rotfleisch & Samulovitch P.C.

Latest Videos

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2024 Budget Changes: Real Estate, Home Taxes And Rentals

FH

FH&P Lawyers

Our "Tax Take" On Canada's COVID-19 Economic Response Plan (Video)

MP

Moodys Private Client Law LLP

Three ways the capital gains tax could change in this budget

CS

Crowe Soberman LLP

CRA Crackdown On Unreported Income From BC Real Estate – Vancouver Tax Lawyer Comments (Video)

RS

Rotfleisch & Samulovitch P.C.

Tax Communiqué: Highlights From The Budget 2013 (Video Content)

HB

Heenan Blaikie LLP

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