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INSIGHTS · CANADIAN TAX RISK

Analysis that holds up when the rules move.

Commentary on CRA administration and Canadian tax law, written for owners, families, and their advisors — every piece dated, cited to primary sources, and revised when the law or CRA practice changes.

Much of what is published on Canadian tax is out of date by the time it matters. The proposed capital gains inclusion-rate increase was cancelled on March 21, 2025 and never became law, yet material asserting the higher rate still circulates widely. A reader who acts on a stale figure pays for it — at filing, in a tax audit, or at a deal table.

This hub runs on a different editorial model: the first correct analysis of a development, not the largest volume of commentary. Every piece carries a visible as-of date, cites primary sources — legislation, CRA publications, court decisions — and is revised when the rules move. What cannot be sourced is not published.

The launch calendar below lists the first seventeen pieces in publication order: the CRA dispute file first; then HST/GST documentation and the sale of a business; then family wealth, real estate, and industry enforcement — with two pieces written for the lawyers, M&A advisors, and bankers who refer matters here. Each article answers one real question and supports one advisory mandate.

Latest

Published analysis

CRA Crisis Advisory

CRA Net Worth Assessment: How It Works and How to Challenge It

How the CRA reconstructs income from lifestyle and bank deposits when the books fall short — and the documented, line-by-line rebuttal that displaces the estimate.

July 10, 2026 · 9 min read

CRA Crisis Advisory

How Far Back Can the CRA Audit You?

The normal reassessment period is three years for most taxpayers — but a year is only truly closed when nothing in it lets the Minister prove misrepresentation.

July 10, 2026 · 6 min read

CRA Crisis Advisory

The 90-Day Clock: What to Do With a Notice of Reassessment

A Notice of Reassessment starts a 90-day objection clock from the date on the notice — here is what that clock protects, how collections behaves while it runs, and the narrower routes if it has already passed.

July 10, 2026 · 9 min read

CRA Crisis Advisory

Voluntary Disclosures Program After October 1, 2025: The New Rules

The CRA rebuilt its Voluntary Disclosures Program on October 1, 2025 — two relief tracks, a lower bar to qualify, and a door that still closes the moment the CRA makes the first move.

July 10, 2026 · 8 min read

CRA Crisis Advisory

What Triggers a CRA Audit in 2026

How the CRA actually selects business files in 2026 — the data-matching triggers, the targeted industries, and what still gets picked at random.

July 10, 2026 · 9 min read

01

HST/GST Documentation and the Sale of a Business

HST/GST Audit Advisory

Input Tax Credits Denied: The Documentation CRA Actually Requires

The most common reason CRA denies input tax credits is missing or invalid supplier GST/HST registration numbers — a documentation defect, not a finding of wrongdoing. This piece sets out the three documentation tiers (under $30, $30–$150, $150 and over), the supplier registry check, and how to build purchase records that hold up in an HST/GST audit.

HST/GST Audit Advisory

HST on Assignment Sales: What GTA Investors Owe

Assignments of pre-construction homes are taxable supplies, and CRA audits them actively. This piece works through what an assignor owes, and why the enhanced Ontario new housing rebate — 100 percent of the provincial portion on eligible homes up to $1 million, for agreements signed April 2026 through March 2027 — largely excludes assignment sales.

Pre-Exit Tax Risk

The Capital Gains Rate That Never Was — and the $1.25M Exemption That Survived

The proposed two-thirds capital gains inclusion rate was cancelled on March 21, 2025 and never became law; the inclusion rate remains 50 percent. The lifetime capital gains exemption increase survived — $1.25 million for qualifying small business corporation shares, indexed from 2026. This piece separates what changed from what only appeared to change, with primary sources.

Pre-Exit Tax Risk

Selling Your Business: The QSBC Tests You Must Pass 24 Months Early

The $1.25 million lifetime capital gains exemption is available only for shares that pass the qualified small business corporation tests — including holding and asset tests that reach back 24 months and cannot be fixed at the deal table. This piece explains each test in plain terms, and why purification work starts two years before a sale, not two weeks.

CRA Crisis Advisory

Gross Negligence Penalties: When CRA Adds 50% — and How to Fight It

Subsection 163(2) lets CRA add a penalty of 50 percent of the understated tax where it can establish gross negligence — and the burden of proving it sits with the Minister, not the taxpayer. This piece covers where courts have drawn the line between carelessness and gross negligence, and how reliance on professional advice figures in a defence.

02

Family Wealth, Real Estate, and Industry Enforcement

Family Enterprise Tax Governance

The Family Trust 21-Year Rule After Bill C-15

Every personal trust faces a deemed disposition of its capital property on its 21st anniversary. Bill C-15, which received royal assent on March 26, 2026, closed the indirect trust-to-trust transfers that once reset the clock under s.104(5.8). This piece explains what planning room remains, and why the working window opens years before the anniversary.

Family Enterprise Tax Governance

Estate Freeze for Ontario Owner-Managers: A Governance Guide

An estate freeze caps the value of the current generation's shares and passes future growth — and the tax on it — to the next. This piece treats the freeze as a governance decision rather than a transaction: valuation discipline, redemption terms, who holds control, and the paper that must exist when CRA asks about it years later.

Real Estate Tax Risk

The Property Flipping Rule: 365 Days, Full Business Income, No PRE

Since January 1, 2023, a gain on a residential property sold within 365 days of purchase is fully taxable as business income and the principal residence exemption is denied, subject to limited life-event exceptions. This piece explains how CRA applies the rule, and where the disputes now sit: intention, exceptions, and properties held just past the line.

Cash-Heavy Business Tax Risk

Driver Inc. and PSB Risk: The T4A Moratorium Is Over

The T4A reporting moratorium was lifted for the 2025 tax year, and Budget 2025 committed $77 million to Driver Inc. and personal services business enforcement. This piece sets out what incorporated drivers — and the carriers that engage them — are now exposed to, and what the PSB rules actually turn on.

CRA Crisis Advisory

Can CRA See Your Bank Account? What Auditors Can Actually Demand

CRA does not watch bank accounts in real time — but in a tax audit it can require banking records from the taxpayer and, with the right process, from the bank directly, and it reads deposits against reported income. This piece explains what CRA auditors can demand, what deposit analysis infers, and why unexplained deposits become assessed income.

03

For Professional Advisors

CRA Crisis Advisory

What Tax Litigators Should Demand From a Net Worth Assessment Rebuttal

Written for tax counsel. A net worth assessment stands until it is displaced, which makes the accounting rebuttal the load-bearing document in the dispute. This piece sets out what a line-by-line methodology rebuttal should contain — opening net worth, non-taxable sources, double-counted deposits, arithmetic — and how counsel and the CPA divide the work.

Pre-Exit Tax Risk

Tax Exposures That Kill Canadian SMB Deals in Diligence

Written for M&A advisors and deal counsel. A recurring set of tax exposures surfaces in diligence and reprices or unwinds Canadian SMB transactions: unremitted HST, shareholder loan balances, personal services business risk, payroll classification. This piece maps each exposure to the diligence request that reveals it — and to the sell-side work that resolves it before a buyer finds it.