Canadian & International Tax Advisory
PE risk, GST/HST, payroll withholding, treaty filings, and CRA compliance — structured correctly from day one.
Who This Is For
This practice is focused on a specific category of cross-border tax work. If your situation falls into one of these categories, we can help.
GST/HST obligations, permanent establishment risk, treaty-based filing requirements.
Payroll registration, Regulation 102 withholding, CPP/EI compliance, employment PE.
Services PE exposure, Regulation 105 withholding waivers, individual cross-border compliance.
Tax due diligence, acquisition structuring, post-closing integration, transfer pricing.
Voluntary disclosure, past non-compliance remediation, CRA audit representation.
We work alongside U.S. advisors as Canadian tax counsel on cross-border files.
Common Trigger Events
Most cross-border tax problems don't start with a CRA audit. They start with an event that creates an obligation — one that often goes unrecognized until it becomes a problem.
Payroll registration, CPP/EI remittances, and potential permanent establishment exposure are triggered from the first pay cheque.
Services performed in Canada by non-residents trigger Regulation 105 withholding obligations and may create a taxable PE under the Canada-U.S. Treaty.
Supplying taxable services to Canadian customers can trigger GST/HST registration obligations — even without a physical presence in Canada.
Non-resident suppliers frequently have unregistered GST/HST obligations. Retroactive registration and penalty exposure can be significant.
A CRA letter, audit notice, or request for information requires an immediate, structured response. Early engagement with counsel matters.
Entity structure, acquisition mechanics, and entry point choices have long-term Canadian tax consequences that are difficult to unwind after the fact.
What U.S. Companies Get Wrong
These are the compliance gaps that create CRA problems — and the ones this practice is built to identify and prevent.
Sending employees or contractors to Canada — even temporarily — can create a taxable presence under the Canada-U.S. Tax Treaty. Most companies discover this after the fact.
Non-residents supplying goods or services in Canada often have GST/HST registration and remittance obligations they aren't aware of. Penalties compound quickly.
Payments to non-resident vendors or employees trigger Regulation 105 and 102 withholding obligations. Failure to withhold creates liability for the Canadian payer.
Intercompany transactions between a U.S. parent and a Canadian subsidiary must be priced at arm's length. CRA is active on this — contemporaneous documentation is required.
Branch vs. subsidiary vs. LP — the choice has long-term tax consequences for repatriation, treaty benefits, and Canadian income tax rates. It is rarely reversible without cost.
Past non-compliance can often be remediated through CRA's Voluntary Disclosure Program — but only if the application is filed before CRA makes first contact.
Services
Advisory, compliance, and dispute resolution — from initial market entry through ongoing Canadian operations. Engagements are scoped and quoted before work begins.
How We Engage
Engagements are scoped in advance. Initial advisory calls, diagnostic reviews, filings, and structuring projects are quoted before work begins.
A 30-minute call to understand your Canadian operations, identify the immediate risks or filing obligations, and determine whether and how we can help. No commitment required.
Where a formal engagement is warranted, you receive a written proposal with defined scope, deliverables, and fixed or capped fees before any work begins.
We work via Zoom and secure document portals. Most U.S. clients manage their entire Canadian tax relationship without travelling to Canada.
Ongoing clients have direct access for questions, planning calls, and time-sensitive CRA matters. Not a call centre. Not a ticketing system.
About the Advisor
Affan Khalid advises U.S. companies, multinationals, and non-residents on Canadian tax structuring, compliance, and CRA dispute resolution. His background includes seven years as a Director at MNP and four years at PwC Canada — the same national-firm experience applied without national-firm billing rates.
iTax CPA is the international tax advisory practice of Lepore & Company Chartered Professional Accountants, Stoney Creek, Ontario. For Canadian corporate tax, accounting, and domestic advisory needs, Lepore & Company provides full-service support alongside this practice.
Tax Insights
Technical notes on cross-border issues drawn from active files and CRA developments. Articles are published as they are completed.
The Canada-U.S. Tax Treaty has a services PE rule that most U.S. companies have never heard of — until CRA audits them. Here is what triggers it and how to structure around it.
Article coming soonIf your U.S. company supplies taxable services to Canadian customers, you likely have a registration obligation — even without a physical presence in Canada.
Article coming soonVDP can eliminate penalties and reduce interest on past non-compliance — but only if the application is filed before CRA makes first contact. Timing is critical.
Article coming soonThe entity choice has long-term consequences on repatriation, treaty access, and Canadian income tax rates. Getting it right at entry avoids costly restructuring later.
Article coming soonGet in Touch
Tell us where your Canadian operations stand. We will identify the immediate risks and compliance gaps — and give you a clear sense of what needs to happen next.
Engagements are scoped and quoted before work begins. The initial call carries no obligation.
For Canadian domestic tax and accounting needs, visit Lepore & Company CPA →