Articles
How long it would take to pay off your income tax upfront, according to a think tank
David Rotfleisch, founding lawyer at Taxpage.com, explains what ‘Tax Freedom Day’ means for Canadian taxpayers.
Fraud victims may be missing thousands of dollars in CRA tax deductions
Toronto tax law firm Rotfleisch & Samulovitch P.C. notes that the classification is not always…
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…
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…
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…
Aggressive tax planning schemes, specially those designed by third parties, will annoy CRA
The Federal Court of Appeal in this case made it clear that true arm’s length…
How disobeying a Federal Court order under the Income Tax Act will result in ‘contempt of court’ charge plus fines & penalties
How disobeying a Federal Court order under the Income Tax Act will result in ‘contempt…
Using AI to prepare legal documents? They might not have lawyer-client privilege protection in Canada (Part 2)
Part 2 - Canadian lawyer-client privilege law: Parallels and precautions
Using AI to prepare legal documents? They might not have lawyer-client privilege protection in Canada (Part 1)
Part 1 – The U.S. ruling: A wake-up call on AI and privilege protection
When fake tax losses lead to CRA gross negligence penalties: The risk of willful taxpayer blindness
When fake tax losses lead to CRA gross negligence penalties: The risk of willful taxpayer…
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…
10 Canadian tax facts you ought to know
With the recent release of Canadian Tax Facts 2026 from David J Rotfleisch, now is…
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…
Taxpayer sought judicial review of CRA’s decision to refuse changing his 2004 income tax return
In Rawlings v AGC, the taxpayer successfully won the right to amend his tax return,…
CRA service levels 2026: Why the agency’s 70 per cent call-answering target is a problem for taxpayers
Moreover, a 70 per cent accessibility target effectively acknowledges that a substantial proportion of taxpayers…
Tax Court clarifies limits of director liability after corporate revival
The Tax Court of Canada has provided important guidance on the scope of director liability…
When taxpayer relief, CPP limitation periods, and procedural finality abandon fairness without a remedy
Tolley v The King is a reminder that developments after tax reassessments, no matter how…
When CRA employees misbehave and make mistakes against Canadian taxpayers
The Canada Revenue Agency distinguishes clearly between employee misconduct and wrongdoing, applying different legal and…
$3.2M tuna becomes a tax lesson: When are promotional ‘loss leaders’ tax deductible in Canada?
Canadian tax law permits aggressive marketing strategies, but it requires that business expenses satisfy statutory…
Case Commentary: HMK v. Quebecor Inc – Federal Court Of Appeal rejects GAAR challenge to using strategy of business losses
The FCA decision reaffirmed that tax efficiency alone does not equate to abuse under GAAR,…
How to deduct “loss leaders,” other outrageous promotional expenses on your Canadian business taxes
What Canadian tax rules apply to the deductibility of promotional expenses? Lessons from a $3.2…
Missing a CRA notice is not an excuse: Tax Court reinforces strict deadlines to GST objections
The Tax Court of Canada’s decision in Ng v. The King used a four-step legal…
When CRA reassesses you beyond the normal period for tax shelters for charitable donations
Canadian tax lawyer and accountant David J Rotfleisch explains how a taxpayer involved in a…
The Methanex Case: Trinidad And Tobago Courts Uphold International Tax Principles, Scrutinize ‘Treaty Shopping’ And Lessons For Canadian Multinational Corporations
For Canadian businesses with international operations, this case highlights how treaty-shopping structures continue to be…
Agreements must be in writing: Hutchings v. the King, a case of Covid-19 rent subsidies
Paper, not promises, matter when it comes to government subsidies to businesses during the pandemic,…
Couture v Canada (Revenue Agency) — How not to conduct a judicial review
Federal Court applications for judicial review must include essential or minimum elements, facts or legal…
When Canadian taxpayers have severe emotional trauma, documentation is key to taxpayer relief requests
The 2025 judicial review of Bifano v Attorney General (2019) demonstrates the need for documentation…
Case Commentary: Schwarz v. HMK – You must appeal within the deadline for tax reassessments
The Tax Court of Canada cannot forgive tax debt. Its jurisdiction is limited to correctly…
Case Commentary: Charlebois v. The King – How NOT to apply for GST/HST rebate for owner-built homes
No rebate for an owner who did not build a home as his primary place…
When CRA reassesses and disallows deductions on rental property expenses — Blecha v. Canada
What expenses can owners deduct from rental properties that produce no income?
In Blecha v The King, the Canada Revenue Agency disputed whether a taxpayer was really renting…
How CRA conducts net worth audits and enforces gross negligence penalties against Canadian taxpayers
David J Rotfleisch dissects the case of a certified management accountant and former employee of…
Can CRA require a taxpayer to prepare net worth audit schedules under the new section 231.1?
While the Canada Revenue Agency’s authority under section 231.1(1)(d) is broad, it is not unlimited,…
Case Commentary: Osman v The King – GST/HST new housing rebate claim denied due to lack of intention to occupy property first
Canadian tax lawyer and accountant David J Rotfleisch explains the clear and settled intention to…
Liberals are pushing ahead with a tax cut on some new homes. Here’s everything you need to know
Now that there’s a five per cent GST elimination for homes of up to $1…
Losses, expenses arising from transactions that are not ‘sufficiently commercial’ may be ineligible to reduce taxes
Case Analysis: Why a business must demonstrate actual business activities before applying for business tax deductions
Loss-trading transactions to avoid paying tax disallowed by Tax Court Of Canada (GAAR rule)
In April 2025, the Federal Court of Appeal (FCA) delivered its judgment on Total Energy Services…
Case Commentary: Ayre v the King – Convoluted charitable gifts made through questionable financing transactions
Canadian tax lawyer and accountant David J Rotfleisch examines donative intent under Section 118.1 of…
Case Commentary: Onischuk v. The King – Tax Court rules cannot override CRA’s statutory requirements
A nil assessment is an objection exception because it is not an assessment and hence…
Case Commentary: Uppal Estate v. the King upholds procedural fairness for Canadian taxpayers in tax litigation
The decision emphasizes the duty of the CRA in Tax Court pleadings and serves as…
A widow is not a spouse: Canadian court saves widow from the CRA’s $100,000 derivative tax assessment
In Enns V Canada, 2025 FCA 14, the timing of an RRSP transfer was critical…
Case Commentary: Yadgar v. The King — When trusting your accountant 100% is not an acceptable defence in the Tax Court Of Canada
Canadian tax lawyer and accountant David J Rotfleisch explains how an immigrant success story went…
Case Commentary: How the CRA abused the voluntary disclosure process for this Canadian taxpayer
The Canada Revenue Agency proposed to reassess the Milgram Foundation after accepting its voluntary disclosure…
How to dispute your tax assessment under Toronto’s 2024 Vacant Home Tax
A hundred thousand tax assessments were reversed in 2023, but the City of Toronto has…
Audio
David Rotfleisch talks taxes as the income tax filing deadline of April 30 looms, on the “Fight Back, with Libby Znaimer” full podcast
David Rotfleisch talks taxes as the income tax filing deadline of April 30 looms, on…
Why are Canadian Retirees Hit So Hard by Taxes?
David Rotfleisch joins Libby Znaimer for a 16-minute interview.
“TurboTax Error Costs Customers Thousands,” on Fight Back with Libby Znaimer
Libby is joined by Laurie Reade, TurboTax Customer and David Rotfleisch, founding Canadian tax lawyer…
Why have you put off filing your taxes?
CBC radio host Amanda Pfeffer asks tax lawyer and chartered accountant David Rotfleisch to analyze…
“Fight Back with Libby Znaimer,” Zoomer Radio
David Rotfleisch and Toronto Councillor Stephen Holyday discuss interest and penalties on late payments to the…
Canadian Tax Lawyer Calls on the Government to Extend the Tax Deadline on Zoomer Radio
Canadian tax lawyer David Rotfleisch was recently featured on Zoomer radio, along with other tax…
What does carbon pricing mean for you?
Prime Minister Trudeau announced on Tuesday the Liberals' federal carbon tax and rebate plan to…
Is the CRA treating you fairly?
The Auditor General says how you're treated by CRA depends on where you live and…
Are the feds coming for your lottery winnings?
Reports suggest the Canada Revenue Agency is looking at taxing your poker winnings. Tax expert…
Television
Global National News
David Rotfleisch comments on a $8.7M settlement that has been reached for a class action…
CBC News & CBC’s “About That” investigative program
Andrew Chang, of CBC’s investigative program “About That,” fact checks with David Rotfleisch on the…
David Rotfleisch interviewed by Andrew Chang, on CBC’s show “About That…capital gains tax”
Canada's capital gains tax increase came into effect on June 25, 2024. Andrew Chang breaks…
“Talking Tax – Segment 3: The tax man is very aware of cryptocurrency: Tax lawyer David Rotfleisch” BNN Bloomberg
David Rotfleisch, founder and senior tax lawyer at Rotfleisch & Samulovitch, goes over tax issues…
“Talking Tax – Segment 2: Tax Tips with David Rotfleisch, managing partner at Rotfleisch & Samulovitch” BNN Bloomberg
David Rotfleisch, managing partner at Rotfleisch & Samulovitch, shares his tax tips with viewers. Watch…
“Talking Tax – Segment 1: Talking Tax with David Rotfleisch, managing partner at Rotfleisch & Samulovitch” BNN Bloomberg
David Rotfleisch, managing partner at Rotfleisch & Samulovitch, answers viewers' questions. Watch this segment by…
Canadian Tax Lawyer Shares Insights on Cryptocurrency Taxation on BNNBloomberg.ca
Canadian tax lawyer David Rotfleisch, founder and senior tax lawyer of Rotfleisch & Samulovitch PC,…
Toronto Tax Lawyer Answers Tax-Related Questions on BNNBloomberg.ca
Toronto tax lawyer David Rotfleisch, founder and senior tax lawyer of Rotfleisch & Samulovitch PC,…
Toronto Tax Expert Shares Tax Tips on BNNBloomberg.ca
Toronto-based tax expert David Rotfleisch, founder and senior tax lawyer at Rotfleisch & Samulovitch PC,…
Canadian Tax Lawyer Featured on CityNews Video Report on CERB Repayments
Canadian tax lawyer David Rotfleisch was featured in a video news report on CityNews ("Self-employed…
Toronto Tax Expert Talks About CERB Repayments in Video Interview on BNNBloomberg.ca
Toronto tax expert David Rotfleisch offered his take on CERB (Canada Emergency Response Benefit) repayments…
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I’ve used Rotfleisch & Samulovitch for complex tax planning matters over the past few years. I’ve found them to be extremely knowledgeable, professional & effective, and would highly recommend them especially for entrepreneurs and their companies. R&S’ legal tax knowledge are a solid complement to the expertise of a quality accountant.
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Pro Tip
Tax Audits in Ontario
There are over 350,000 tax audit and review actions conducted by the Canada Revenue Agency on a yearly basis. Around 15,000 of these tax audits deal with “cash only” businesses (i.e. the underground economy). Additionally, an estimated 35,000 are tax shelter audits.