Canada: Capital Gains Tax

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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.

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

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.

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

RS

Rotfleisch & Samulovitch P.C.

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

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

Gains En Capital Ou Dividendes Réputés ? Vos Clients Propriétaires D’entreprises Familiales Sont-ils Prêts Pour Les Nouvelles Règles Relatives Aux TIE ?

MT

Miller Thomson LLP

Ontario Court Reinforces Finality Of Class Proceedings In Rejecting Late Opt-Out Request

Canada Litigation

BJ

Bennett Jones LLP

C$10 Million Capital Gains Exemption Made Permanent For Employee Ownership Trusts

BJ

Bennett Jones LLP

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.

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

International Crypto Fraud Crackdown: How CRA Treats Tax Losses From Crypto Scams In Canada

RS

Rotfleisch & Samulovitch P.C.

Supreme Court Of Canada Denies Leave In Wolastoqey Nation’s Aboriginal Title Claim

Canada Litigation

C

Cassels

Crypto Tax Lawyer's Guide To DeFi, Yield Farming, & Liquidity In 2026

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.

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

The Tax on Split Income (TOSI) rules remain among the most complex and misunderstood areas of Canadian private corporation tax planning.

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

Canadian crypto tax compliance has entered a fundamentally different phase—one driven by data visibility, artificial intelligence, and targeted enforcement. The longstanding assumption that cryptocurrency transactions operate outside regulatory reach is no longer credible.

RS

Rotfleisch & Samulovitch P.C.

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

Crypto in divorce in Canada presents unique hurdles for couples managing Bitcoin, Ethereum, and other digital assets amid separation.

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.

Crypto Tax Lawyer's Guide To DeFi, Yield Farming, & Liquidity In 2026

RS

Rotfleisch & Samulovitch P.C.

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

LL

Lerners LLP

Ottawa Makes $10-million EOT Exemption Permanent

MT

Miller Thomson LLP

Vente d’entreprise : les stratégies fiscales pour maximiser vos économies d’impôt

BB

BCF Business Law

Business Sale: Tax Strategies To Maximize Your Tax Savings

BB

BCF Business Law

Ottawa rend permanente l’exonération de 10 M$ pour les FCE

MT

Miller Thomson LLP

A Tax Lawyer’s Guide To The Luxury Tax In Canada

RS

Rotfleisch & Samulovitch P.C.

I Am A Beneficiary Of BC Real Property – What Taxes Should I Seek Advice On?

AH

Alexander Holburn Beaudin + Lang LLP

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

Crypto in divorce in Canada presents unique hurdles for couples managing Bitcoin, Ethereum, and other digital assets amid separation.

RS

Rotfleisch & Samulovitch P.C.

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

Cryptocurrency has become a significant source of wealth for many Canadians. Whether an individual holds Bitcoin as a long-term investment, actively trades digital assets, participates in staking programs, or engages in decentralized finance (DeFi), cryptocurrency can create unique estate planning challenges that do not arise with traditional investments.

RS

Rotfleisch & Samulovitch P.C.

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

The Canada Revenue Agency (CRA) has significantly expanded its cryptocurrency tax enforcement efforts in recent years.

RS

Rotfleisch & Samulovitch P.C.

Crypto Tax Lawyer's Guide To DeFi, Yield Farming, & Liquidity In 2026

Decentralized Finance (DeFi) continues to deliver strong opportunities for Canadian crypto investors through yield farming, lending, liquidity provision, and staking.

RS

Rotfleisch & Samulovitch P.C.

Crypto Tax Reporting: Canada vs. U.S. (2026); CRA Digital Asset Rules Compared To IRS Form 1099-DA Reporting

RS

Rotfleisch & Samulovitch P.C.

Crypto Tax Lawyer's Guide To DeFi, Yield Farming, & Liquidity In 2026

Decentralized Finance (DeFi) continues to deliver strong opportunities for Canadian crypto investors through yield farming, lending, liquidity provision, and staking.

RS

Rotfleisch & Samulovitch P.C.

Crypto Tax Reporting: Canada vs. U.S. (2026); CRA Digital Asset Rules Compared To IRS Form 1099-DA Reporting

The rapid evolution of digital asset taxation has led to significantly different reporting frameworks in Canada and the United States.

RS

Rotfleisch & Samulovitch P.C.

Closing The Loophole On Indirect Trust Transfers And The 21-Year Deemed Disposition Rule: New Measure In Budget 2025

For Canadian tax planners and trust beneficiaries, the “21-year rule” is a critical milestone.

RS

Rotfleisch & Samulovitch P.C.

Post-Mortem Planning Just Got A Little Bit Easier: Amendments To 164(6) Loss Carryback

Recent amendments to Canada's Income Tax Act have extended the post-mortem loss carryback election from one to three taxation years, providing estate administrators significantly more time to implement tax planning strategies.

GR

Gardiner Roberts LLP

The Stock Option Buyout Trap: Why A Canadian Tax Lawyer Says Tax Timing Is Everything

RS

Rotfleisch & Samulovitch P.C.

Property Transfers And Flipped Property Rules Under Section 85 Of The ITA: A Welcome Flexibility For Internal Reorganizations

MT

Miller Thomson LLP

Stress-Testing The U.S. Flip: Benefits Of Canadian Incorporation

F

Fasken

Employee Ownership Trusts: A New Succession Planning Option For Canadian Business Owners

FR

Fillmore Riley

Déménager Son Siège Social Aux États-Unis : Est-Ce Vraiment Judicieux?

Canada Commercial

FF

Fasken (French)

Canada Crypto Voluntary Disclosure: How Amicarelli v. The King Shows That Many Crypto Profits May Be Business Income—Not Capital Gains

RS

Rotfleisch & Samulovitch P.C.

Tax Alert: $10 Million EOT Tax Exemption Made Permanent

CW

Clark Wilson LLP

Spring Economic Update 2026

OH

Osler, Hoskin & Harcourt LLP

Spring Economic Update 2026: Key Tax Changes To Watch

MT

Miller Thomson LLP

Dix faits saillants fiscaux de la Mise à jour économique du printemps de 2026 du Canada

BL

Borden Ladner Gervais LLP

Noël c. Birk : comment la fiscalité influence le partage d'un FERR

MT

Miller Thomson LLP

Acheter une résidence de vacances aux États-Unis : un Canadien devrait‑il utiliser une fiducie ?

MT

Miller Thomson LLP

Canadians Buying A U.S. Vacation Property: Should You Use A Trust?

Canada Real Estate

MT

Miller Thomson LLP

Update On The Capital Gains Exemption And Qualified Small Business Corporation Shares

OE

O'Sullivan Estate Lawyers LLP

Points clés à retenir des Perspectives fiscales de McCarthy Tétrault : janvier et février 2026

MT

McCarthy Tétrault LLP

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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.

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.

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.

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