David J. Rotfleisch
Tax Law
Recent Blog Posts By David J. Rotfleisch
Opinion: Donating to a registered charity is not wrongdoing
Canadian tax lawyer and accountant David J Rotfleisch on what a recent article by the IJF about the Asper Foundation gets wrong about Canadian charity law
Federal Court sets strict Mutual Agreement Procedure (MAP) deadline in reassessment deals with Canada Revenue Agency
The FC Robinson MAP deadline ruling has implications for cross-border taxpayers, owner-managers, corporate groups, and accountants, says David J Rotfleisch
Notice of Assessment was never mailed? Federal Court of Appeal clarifies taxpayer must first prove non-delivery
The FCA Siam decision reinforces that taxpayers bear the burden of proving that a Notice of Assessment was not sent, and credibility plays a central role
Complaints about CRA rise 27% despite recent automated tax filing, call centre failures, processing delays, poor communication
Canada’s tax act is completely nuts; administrative modernization cannot succeed without legislative simplification, asserts tax lawyer David J Rotfleisch
Why R v Jarvis is the most important tax case for Canadian taxpayers
The 2002 Supreme Court of Canada decision presents a clear line between a CRA tax audit versus a criminal tax investigation, explains David J Rotfleisch
Tax Court confirms that taxpayers must provide clear instructions to apply refund balances
A recent Tax Court decision in BMLex Avocats v The King explains why a tax credit balance does not protect taxpayer from GST/HST instalment interest
When the CRA recharacterizes capital gains as business income: Happy Valley Farms, Stewart v. Canada
Canadian tax lawyer and accountant David J Rotfleisch dissects the legal framework, playbook governing Canada Revenue Agency audits, reassessments
Why detailed record-keeping is critical to deducting business expenses with CRA: Bobic v. The King
Tax Court of Canada decision yields generous outcome due to CRA benefit of the doubt test, explains Canadian tax lawyer and accountant David J Rotfleisch
King Charles taxation and Canadian comparisons: Voluntary compliance, crown privilege, and tax transparency
Underlying themes of taxation have direct resonance for Canadian taxpayers and their advisors, asserts Canadian tax lawyer and accountant David J Rotfleisch
Panama Papers 10th anniversary: Canadian tax implications, CRA results & compliance lessons for taxpayers
The Panama Papers significantly raised the visibility and compliance costs of offshore secrecy, explains Canadian tax lawyer and accountant David J Rotfleisch
How the CRA uses artificial intelligence in Canadian tax audits: What taxpayers must know now
Taxpayers flagged in error by Canada Revenue Agency AI algorithms have no front-end remedy, argues Canadian tax lawyer and accountant David J Rotfleisch
CRA’s conduct slammed for unnecessarily prolonging tax litigation, increasing costs
Why the Federal Court of Appeal upheld a Tax Court of Canada decision to award costs to Marine Atlantic in its appeal of a Canada Revenue Agency assessment
Forgotten, missing tax records and unreported income will cost you penalties
Karlozian serves as a cautionary example of the risks of poor record-keeping and incomplete tax reporting, says tax lawyer and accountant David J Rotfleisch
Withholding tax and beneficial ownership: C&W Offshore Ltd. v. HMK, 2026 TCC 40
A non-resident vendor’s silence on an invoice does not relieve a Canadian resident of its statutory duty to withhold and remit tax under the Income Tax Act
How to beat CRA alternative tax assessments: Insights from a Canadian tax lawyer
Canadian tax lawyer and accountant David J Rotfleisch presents four strategies based on recent judicial decisions to undermine these CRA tax assessments
Aggressive tax planning schemes, specially those designed by third parties, will annoy CRA – Canada v. Microbjo Properties Inc.
The Federal Court of Appeal in this case made it clear that true arm’s length dealings require independent interests, real negotiation, and genuine risk
How disobeying a Federal Court order under the Income Tax Act will result in ‘contempt of court’ charge plus fines & penalties
As David J Rotfleisch explains, the courts make a clear distinction between the inability to comply and a lack of effort, when it comes to contempt of court
When fake tax losses lead to CRA gross negligence penalties: The risk of willful taxpayer blindness
The recent McCutcheon decision reinforces a fundamental principle of Canadian tax litigation, explains Canadian tax lawyer and accountant David J Rotfleisch
CRA real estate tax audits using MLS data: Builder risk, GST/HST exposure & audit defence strategies In Canada
In one year alone, more than 2,200 GST/HST tax audits specifically targeting housing transactions resulted in approximately $231 million in tax assessments
How to avoid the 'tax trap' on timing of flow-through for dividend income and timing of receipts for trusts
Canadian tax lawyer and accountant David J Rotfleisch examines the FCA decision in Vefghi Holding Corp. v. Canada, currently under leave to appeal at the SCC
CRA may apply 2025 permanent establishment OECD rules to Canada
Canadian tax lawyer and accountant David J Rotfleisch on remote work, corporate authority to bind, CRA treaty interpretation and interprovincial tax risk
Contempt of court in Canadian tax litigation is a high bar in Canada
The MNR v Carflex decision illustrates the high evidentiary threshold that must be satisfied before a taxpayer or corporate officer can be found in contempt
Unpaid payroll deductions: Federal Court Of Appeal affirms bona fide purchaser defence for unsecured creditors
Toronto-Dominion Bank v. Canada confirms that innocent unsecured creditors are not automatically liable to repay unremitted payroll deductions to the Crown
When a donation is not really a gift: The court's rejects on tax-driven charity arrangements, gifts must be genuine
The Federal Court of Appeal decision in Walby v Canada reinforces an important principle in Canadian tax law, says tax lawyer and accountant David J Rotfleisch
Canada's anti-deferral regime and the FAPI rules: When offshore trust structures trigger more tax
A common misconception in offshore tax planning is that tax treatment of foreign trusts is determined solely by where the trust is administered or governed
