Tax Dispute Caselaw & Signals

Signals from CRA disputes that reveal how outcomes are decided.

Counter Sphere 1 Image, with “When Corporate Losses Require More Than Mechanics” title text, judgment-driven advocacy for CEOs and CFOs managing high-stakes CRA disputes

Key Takeaways The mechanics worked, but the Court focused on whether the reorganization produced a real economic loss or merely a paper one. That distinction shaped the GAAR outcome. The decisive batt...

Counter Sphere 1 Image with

Key Takeaways Enhanced costs continue to rise. The Tax Court again imposed enhanced costs on the Crown, reinforcing a pattern: disciplined conduct in the right arena creates financial consequences tha...

Background Pattern 2 with Caselaw Insights text - Framing Gaps in SR&ED Disputes Shift Control to CRA, superior tax dispute representation for high-stakes cases by Counter Tax Litigators LLP.

Key Takeaways Framing gap: The Tax Court accepted CRA’s framing because Vortex’s reply lacked engineering support and legal positioning. In other disputes, when claims were framed with qualified techn...

Background Pattern 2 with Caselaw Insights text – Hidden Tax Risks in Corporate Life Insurance, on high-stakes tax disputes involving mature businesses and affluent families.

Key Takeaways Premium payments as benefits: When one company pays premiums on a policy owned by another, courts treat it as a taxable benefit — intent does not override structure. Expanding reach of s...

Background Pattern 2 with Caselaw Insights text - The Evolving Landscape of Supply Classification, reaffirming that only tax statutes—not invoices or regulations—define separate supplies.

Key Challenge: Clarifying GST/HST Supply Classification Integrated Transactions: Tax professionals should proactively evaluate whether elements of a purchase are truly independent or part of a single ...

Background Pattern 2 with Caselaw Insights text - Choose the Right Beneficiary to Avoid Tax Pitfalls, unique expertise in overturning CRA reassessments by Counter Tax Litigators LLP.

The Federal Court of Appeal’s (“FCA”) decision in Enns v. Canada[1] clarifies how “spouse” is defined for purposes of paragraph 160(1)(a) of the Income Tax Act (“ITA”). This decision carries significa...

Background Pattern 2 with Caselaw Insights text - Non-CCPC Planning and GAAR Boundaries, strategic tax dispute navigation with deep legal expertise by Counter Tax Litigators LLP.

Executive Summary: The Tax Court drew a hard line: choosing non-CCPC status before a sale is not abuse, at least until Parliament closed the door in 2022.