Canada: FinTech

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Accounting law and audit law thought leadership, articles, podcasts, videos and webinars from expert sources across the legal world. Explore insights covering topics such as FinTech, marketing, media, new technology, security.

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.

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.

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.

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.

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

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.

FINTRAC Money Services Business Registration (MSB Licence)

MC

Michael Chambers & Co. LLC

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.

OSFI’s Streamlined Bank Incorporation Framework: What Eligible Applicants Need To Know

OH

Osler, Hoskin & Harcourt LLP

From 4% Random Selection To 100% Audit Risk: How CRA’S AI-Driven Audits Are Changing Tax Enforcement For Canadians

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.

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.

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.

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

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.

Can You Terminate An Employee Who Is On A Leave?

Canada Employment

FR

Fillmore Riley

A Costly Reminder For Employers: Employee Awarded Nearly $200,000 For OHSA Reprisal

Canada Employment

WL

WeirFoulds LLP

Remote Work As An Accommodation: No Longer Exceptional But Not Automatic

Canada Employment

F

Fasken

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.

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.

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

Online content creation has become a serious source of income for many creators. Recent reports suggest that actress Shannon Elizabeth earned more than seven figures in her first week on OnlyFans platforms, even if the platform is foreign or the payments are processed outside Canada.

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.

CRA Phishing Scams And CRA Impersonation Fraud In Canada: What Taxpayers Need To Know About Identity Theft And Tax Fraud

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.

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

RS

Rotfleisch & Samulovitch P.C.

CRA vs. IRS Audits: What Every Canadian Tax Lawyer Wants You To Know

RS

Rotfleisch & Samulovitch P.C.

Proposed Consumer-Driven Banking Regulations Released For Comment

BC

Blake, Cassels & Graydon LLP

Canada’s Consumer-Driven Banking Framework Takes Shape With Draft Regulations

MT

McCarthy Tétrault LLP

OSFI Officially Launches Targeted Fast-track New Entry Regime

TL

Torys LLP

Update From OSFI Industry Day: What Credit Unions And Fintechs Need To Know About OSFI’s New Streamlined Process For Entering Canada’s Federal Financial System

Canada Technology

MT

McCarthy Tétrault LLP

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

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.

CRA vs. IRS Audits: What Every Canadian Tax Lawyer Wants You To Know

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.

CRA vs. IRS Audits: What Every Canadian Tax Lawyer Wants You To Know

Cross-border taxpayers, corporations, investors, and high-net-worth individuals increasingly face scrutiny from both the Canada Revenue Agency (CRA) and the Internal Revenue Service (IRS).

RS

Rotfleisch & Samulovitch P.C.

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

A recent international law enforcement operation has highlighted the growing scale and sophistication of cryptocurrency fraud, while simultaneously raising complex tax issues for Canadian victims.

RS

Rotfleisch & Samulovitch P.C.

Toronto Crypto Crackdown Intensifies Enforcement And CRA Tax Audit Risk

Recent enforcement activity in Toronto has escalated into a large-scale regulatory crackdown on cryptocurrency businesses.

RS

Rotfleisch & Samulovitch P.C.

Canadian Regulators’ Responses To Recent Technological Innovations

Canada Technology

C

Cassels

Principales répercussions de la Mise à jour économique du printemps de 2026 sur le secteur financier canadien

BC

Blake, Cassels & Graydon LLP

Blockchain-powered Payments And The Canadian Payments Landscape (Podcast)

TL

Torys LLP

Fintech Patents: Allowance Trends At The Canadian Patent Appeal Board

BJ

Bennett Jones LLP

OSC Requests Comments On Proposed Amendments To Fee Rules

WD

Wildeboer Dellelce LLP

Competition, Crypto, And Crime: Financial Services And Technology Highlights From The Spring Economic Update 2026

GW

Gowling WLG

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.

Blockchain Powered Payments: How Stablecoins, Tokenized Deposits, And Digital Payment Instruments Can Reshape The Canadian Payments Landscape

Canada Technology

TL

Torys LLP

Canada Proposes To Expand Application Of Investment Canada Act To Foreign Banks And Move Forward With Expanding Fintech Investment Powers

TL

Torys LLP

Have Your Say – Part 1: Canadian Patent Office Seeking Input On Expedited Examination

TL

Torys LLP

Toronto Crypto Crackdown Intensifies Enforcement And CRA Tax Audit Risk

RS

Rotfleisch & Samulovitch P.C.

The Future Of Fintech: Q&A With Jay Dorey

Canada Technology

TL

Torys LLP

Canada’s New Approach To Financial Crime: Federal Financial Crimes Agency Announced

Canada Criminal

GW

Gowling WLG

Canada’s Proposed Stablecoin Framework – Key Legal And Regulatory Takeaways

Canada Technology

MA

MLT Aikins LLP

Crypto In Divorce: How We Find It, Value It, And Prove Ownership

LL

Lerners LLP

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.

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

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.

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

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

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.

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

RS

Rotfleisch & Samulovitch P.C.

CRA Phishing Scams And CRA Impersonation Fraud In Canada: What Taxpayers Need To Know About Identity Theft And Tax Fraud

RS

Rotfleisch & Samulovitch P.C.

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

RS

Rotfleisch & Samulovitch P.C.

Latest Videos

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The Dawn Of A New Era For Payment Service Providers: Navigating The Retail Payment Activities Act Regime

GW

Gowling WLG

U.S. Court Sends Ripple Through Murky Waters Of Crypto Regulation (Video)

OH

Osler, Hoskin & Harcourt LLP

The Canadian Fintech Review: Privacy, Cybersecurity, Data And AI (Video)

TL

Torys LLP

Blockchain Part 1: Frontier Of Change (Video)

D

Dentons Canada LLP

Dealing With Digital (Video)

BL

Borden Ladner Gervais LLP

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