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  • Article

    How To Deal With CRA Tax Problems

    The normal reassessment period rule is a rule that is usually used to the taxpayer's advantage. Generally, it prevents CRA from reassessing a taxpayer for a particular tax year after three years have elapsed.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Judicial Review Of Remission Order Application

    The Remissions Order Application by an experienced Canadian tax lawyer under subsection 23(2) of the Financial Administration Act is often taken to be a last-ditch resort at tax relief for Canadian taxpayers when all other tax disputes ...
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Updates To CERS, CEWS & CEBA: Canadian Tax Lawyer Analysis

    Many Canadian businesses have been impacted by the ongoing COVID-19 pandemic. While some businesses are able to operate but not at full capacity, others are forced to temporarily shut down due to public health orders.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Wall v Canada, 2021 FCA 132 – Guidance From A Canadian Tax Lawyer On Taxation Of House Flipping

    Mr. Wall was a licensed real estate agent in Vancouver. From 2004 to 2010, he bought and sold three properties and the transactions all had a similar fact pattern.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    What Is CRA's Regulation 105? An Overview On Withholding Tax On Payments To Non-Residents, Explained By Canadian Tax Lawyer

    When non-residents provide services in Canada, a lesser-known but critical piece of tax legislation comes into play: Regulation 105 of the Income Tax Regulations.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    When Full Business Income Tax, Other Than Capital Gains Tax, Is Payable If Business Activities Are Based On A "Secondary Intention" Tax Law Doctrine In An "Adventure In The Nature Of Trade" – Guidance From A Canadian Tax Lawyer

    The tax treatment of income in Canada depends on its classification, making it essential for taxpayers to understand the nature of the income they earn in order to file tax returns accurately and engage in effective tax planning.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Why 'Primary Residence Intent' Matters To Residential Real Estate Owners, Investors: GST/HST New Housing Rebate – Lisi v. The King (2025 TCC 106)

    The GST/HST New Housing Rebate, as outlined in section 254 of the Excise Tax Act, offers essential relief to Canadians purchasing a newly built home. To qualify, however, Parliament imposed a strict condition.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    How U.S. Businesses Can Deduct Outrageous Marketing "Loss Leaders" Expenses On Their Taxes: Lessons From A $3.2 Million Bluefin Tuna Purchase

    Extraordinary promotional expenditures often attract scrutiny from the Internal Revenue Service (IRS), particularly when the amount paid for a single item appears disconnected from its intrinsic value.
    United StatesTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Rental Income, Corporations & Specified Investment Business

    Operating a business through a corporation can lead to significant deferral advantages over time.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    The Queen v Paletta – Guidance From A Canadian Tax Lawyer Regarding The Legal Test For Business Income

    In the Queen v Paletta, 2022 FCA 86, the Canadian tax litigation lawyer acting for the CRA appealed the Tax Court of Canada's decision regarding Mr. Pasquale Paletta's appeals from reassessment regarding the 2000 through 2007 taxation years.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Canadian Crypto Tax Lawyer's Review Of The Terra Collapse And Do Kwon's Guilty Plea

    The 2022 collapse of TerraUSD (UST) and Luna erased nearly $60 billion in global value and remains one of the most disruptive failures in cryptocurrency history.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Non-Resident Withholding Tax – Interest Income – A Toronto Tax Lawyer Analysis

    The Canadian income tax regime differs for resident taxpayers and non-resident taxpayers in Canada.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Tax Lawyer Analysis: CRA's Broad Powers To Compel Third Party Information Under Section 231.2 Is Not Without Limits

    The CRA derives its power to conduct tax audits against taxpayers under section 231.1 of the Income Tax Act.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Vefghi Holding Corp. v. Canada: How To Avoid The "Tax Trap" On Timing Of Flow-Through For Dividend Income And Timing Of Receipts For Trusts

    For Canadian tax planners and business owners, utilizing inter vivos trusts to flow income through from corporations to beneficiaries is a common strategy for tax deferral and to multiply access to the lifetime capital gains exemption.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    When Are Food Expenses, Meal Expenses Deductible In Canada? Reasonable Expenses When Travelling Is Required For Work, Says Canadian Tax Lawyer

    The Income Tax Act and case law allow for various deductions for employees and businesses. Many of these deductions relate to costs incurred to produce income.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Canadian Shopify Merchants Beware: The Canada Revenue Agency Is Coming

    The Canada Revenue Agency wants to know whether Canadian e-commerce merchants using Shopify have been accurately reporting their sales.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Repeated Failure To Report Income Tax Penalty

    Canada's income tax system is designed around every taxpayer filing an annual return which reports all of the income that taxpayer earned during the year.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    CRA Finally Unveils 100-Day Service Improvement Plan For 2025: How Canadian Taxpayers Should Benefit

    In 2025, Canadians faced prolonged delays with the CRA, including call answer rates below 40%in July 2025 and lengthy processing backlogs for T1 tax adjustments.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Case Commentary: Ayoub v The King, 2025 TCC 48 – Beware Home Builders Must Pay HST/GST When Renting Or Using Property Personally (Self-Supply Rule)

    In March 2025, the Tax Court of Canada delivered its judgment on Ayoub v The King, 2025 TCC 48, related to the assessment by the CRA on the taxpayer, Michael Ayoub, for director's liability under subsection 323(1) of the Excise Tax Act.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.
  • Article

    Changes To The Eligible Capital Property Tax Rules: How Rotfleisch & Samulovitch Can Help You Protect Your Hard-Earned Goodwill

    The new tax rules will result in higher taxes on the sale of Goodwill and the inability to defer income from the sale of a business using a corporation.
    CanadaTax
    Rotfleisch & Samulovitch P.C.
    Rotfleisch & Samulovitch P.C.

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