David J. Rotfleisch

Tax Law

David Rotfleisch

David J. Rotfleisch, CPA, CA, JD, is the founding Canadian tax lawyer of Rotfleisch & Samulovitch, P.C., a Toronto-based boutique income tax law firm (Taxpage.com). With over 30 years of experience as both a lawyer and chartered professional accountant, he has helped start-up businesses, resident and non-resident business owners and corporations with their tax planning, with will and estate planning, voluntary disclosures and tax dispute resolution including tax litigation. Contact David at david@taxpage.com.

Recent Blog Posts By David J. Rotfleisch

CRA's ex parte jeopardy order application must provide full and frank disclosure

Canadian tax accountant and lawyer David J Rotfleisch on a win in Federal Court in a high-profile tax case and a lack of full and frank disclosure from the CRA

Tax settlement In Canadian tax litigation: Challenges for Canadian taxpayers

Canada's courts say a CRA settlement must be principled and not a compromise, explains Canadian accountant and tax lawyer David J Rotfleisch

CRA to introduce new automatic tax filing system as many Canadians miss out on benefits

Tax filing and tax software groups have been actively discouraging the CRA and its U.S. equivalent, the IRS, from implementing automatic returns

Lawyer-client confidentiality may fail to protect end-product tax documents, says FCA

The BMO Nesbitt Burns decision draws a distinction between legal advice and end-product documents says tax lawyer and accountant David J Rotfleisch

How to legitimately defer the worst of Canada's departure tax when becoming a non-resident and moving to another country

The departure tax can create a substantial and unforeseen tax bill for the unaware emigrating taxpayer explains tax lawyer and accountant David J. Rotfleisch

Burden of proof for misrepresentation in tax reassessments is high — and rests with the CRA

In a recent Tax Court of Canada case, the Canada Revenue Agency's proof was flimsy, says Canadian accountant and tax lawyer David J Rotfleisch

GST/HST tax fraud is a ‘special operation' at the Canada Revenue Agency

It involves fraudulent refund claims, fake invoicing, and GST/HST evasion through off-the-books cash sales, explains tax lawyer and accountant David J. Rotfleisch

When the CRA reassessed a taxpayer's tax returns beyond the normal reassessment period

Canadian accountant and tax lawyer David J. Rotfleisch explains how, in Goldhar v The King, a toy salesman successfully appealed a CRA reassessment

Trustees need to be prepared for new trust reporting rules

Canadian accountant and tax lawyer David J Rotfleisch explains the new trust reporting rules to take effect In the 2023 taxation year

When a tax-free savings account is a business & stripped of tax benefits

David J Rotfleisch comments on a recent Tax Court of Canada case

SR&ED: The CRA cannot use its civil tax audit power to gather information for a criminal investigation

David J Rotfleisch explains why the Federal Court of Appeal ruled in favour of the CRA in a Scientific Research and Experimental Development tax credits case

Sweet v Canada: Federal Court Of Canada certified privacy breach class action against CRA

Canadian accountant and tax lawyer David J Rotfleisch on the latest privacy class action lawsuit to be certified by the Federal Court of Canada

The reasonability requirement for administrative suspension of EFILE rights

Canadian tax lawyer and accountant David J Rotfleisch on Virgen v Canada (Attorney General), a Federal Court decision in favour of an Ontario tax preparer

Rectification saves taxpayers from adverse tax consequences arising from drafting error

A KPMG tax planning document saved Sleep Country from the consequences of a numerical error, explains Canadian accountant and tax lawyer David J Rotfleisch

Another historical development in claiming negligence against the CRA

Canadian accountant and tax lawyer David J Rotfleisch on the Myers ruling

Singh v. Canada: A Canadian tax lawyer's observations on TFSA penalties

As taxpayers, we are ultimately responsible for meeting our obligations under tax law, as explained by Canadian accountant and tax lawyer David J Rotfleisch

Tax Court orders CRA to release GAAR committee reports about similarly situated taxpayers

Canadian accountant and tax lawyer David J Rotfleisch explains why the Committee's legal analysis fell within within the scope of discovery

The Ontario Ministry Of Finance's Voluntary Disclosures Program – A Canadian tax lawyer's summary

David J. Rotfleisch explores the differences between the federal and Ontario VDPs

Preston Family Trust II v The Queen: Assumptions of facts in replies to a notice of appeal

Just the facts, ma'am: David J. Rotfleisch explains why the Tax Court of Canada would strike out the CRA's legal assumptions in a notice of appeal

New proposed mandatory tax planning reporting obligations under the Canadian Income Tax Act

Amendments to the new rules were made in August 2022 and are likely to become law says Canadian accountant and tax lawyer David J Rotfleisch

Barrs v The Queen: Taxpayer relief under S.220(3.1)

Canadian accountant and tax lawyer David J Rotfleisch on a Federal Court of Appeal case involving a CRA's review officer's failure to engage with a request for equitable treatment

MNR v Zhao: CRA collection action when there are reasonable grounds for delay

Canadian accountant and tax lawyer David J Rotfleisch on the Canada Revenue Agency’s successful jeopardy order in a high-profile BC real estate case

Tax pipeline planning: A Canadian tax lawyer's guide and case study

A pipeline plan is a tool used to avoid paying tax on dividends to pay tax on capital gains explains David J Rotfleisch

FCA overturns Tax Court's decision because the CRA's evidence was about the taxpayer’s spouse

Canadian accountant and tax lawyer David J. Rotfleisch on the Khanna v The Queen decision by the Federal Court of Appeal, which overturned a Tax Court ruling

The Queen v Paletta – The legal test for business income

Tax lawyer and accountant David J. Rotfleisch on the CRA's successful appeal of a Tax Court of Canada ruling regarding foreign currency trading