Search reassessments, business deductions, residency disputes, GST issues, director liability, and more — backed by real case law.
Tax disputes involve reassessments, deduction challenges, residency questions, and penalties backed by agencies with enormous investigative power — Casey searches millions of court decisions across Canada and the US to show how judges have ruled on similar tax controversies.
Tax disputes involve reassessments, deduction challenges, residency questions, and penalties backed by agencies with enormous investigative power — Casey searches millions of court decisions across Canada and the US to show how judges have ruled on similar tax controversies.
Real Scenarios
1
Reassessments, Objections & Appeals
When the CRA or IRS reassesses a taxpayer, the first step is usually filing an objection. If the agency refuses to change its decision, the case may go to tax court. Courts evaluate reasonableness and the taxpayer's evidence.
Prompt:
“What decisions describe successful challenges to CRA reassessments?”
Casey retrieves rulings analyzing documentation, credibility, statutory interpretation, and procedural fairness.
2
Income vs Capital Disputes
Many tax controversies turn on whether income should be treated as business income or capital gains. Courts examine intention, frequency of transactions, expertise, risk, and business structure.
Prompt:
“How have courts distinguished business income from capital gains?”
Casey retrieves decisions showing patterns courts rely on when evaluating real estate flips, investments, and securities trading.
3
Business Expenses & Deductibility
Taxpayers often claim deductions that CRA or IRS later reject. Courts must decide whether the expenses were reasonable, necessary, documented, and incurred to earn income.
Prompt:
“What cases allowed business expense deductions after a CRA challenge?”
Casey retrieves rulings involving travel, marketing, home offices, vehicle use, subcontractors, and professional services.
4
Residency & Cross-Border Tax Issues
Residency determines which country has taxing rights. Disputes arise when taxpayers move, spend long periods abroad, or operate businesses in multiple jurisdictions.
Prompt:
“What decisions interpret residency for tax purposes?”
Casey retrieves rulings analyzing centre of vital interests, family ties, home availability, travel patterns, and tax treaties.
5
GST, HST & Input Tax Credit Disputes
Sales tax creates complex controversies. Businesses dispute whether they collected the correct amount, whether transactions were exempt, or whether input tax credits were valid.
Prompt:
“How have courts ruled on denied input tax credits?”
Casey returns rulings examining documentation, fraudulent suppliers, verification standards, and burden of proof.
6
Payroll, Remittances & Director Liability
If a corporation fails to remit payroll or GST amounts, directors can be held personally liable. Courts evaluate whether directors exercised due diligence.
Prompt:
“What decisions address director liability for unremitted payroll taxes?”
Casey retrieves rulings analyzing delegation, oversight, records, and financial controls in director liability cases.
Real Scenarios
When the CRA or IRS reassesses a taxpayer, the first step is usually filing an objection. If the agency refuses to change its decision, the case may go to tax court. Courts evaluate reasonableness and the taxpayer's evidence.
Prompt:
“What decisions describe successful challenges to CRA reassessments?”
Casey retrieves rulings analyzing documentation, credibility, statutory interpretation, and procedural fairness.
Corporate directors can be held personally liable for unremitted payroll and sales taxes — even if they had no direct involvement in the company's finances. The only defence is proving due diligence.
Ask Casey your question and get answers backed by real case law — free for the public, powerful for professionals.