The IRS And CRA Double Tax Trap For Canadians
What no one tells you about the million-dollar tax traps, IRS penalties, and the entity mismatch that can bankrupt your investment.
- Estate Planning
- Business Sale
- Corporate Reorganization
- Trust Planning
- Family Trust
- Succession Planning
- Tax Compliance
- Penalties & Interest
- Business Owners
- Founders & Entrepreneurs
- Partnership
- Sale-Readiness
- US Tax
- Cross-Border
- US LLC
- IRS
- Wills & Estates
- Legal Perspective
Show Notes
In this episode, we sit down with US Tax Specialist, Sandy Saini, to uncover why forming a U.S. LLC – often promoted as a simple and tax-efficient structure – can quickly turn into a costly mistake for Canadian residents.
While LLCs offer flexibility and liability protection in the United States, the way Canadian tax law treats these entities creates a serious mismatch that can lead to unexpected reporting obligations, double taxation, and significant penalties.
Through This Deep Dive, We Break Down:
• Why U.S. LLCs are often unsuitable for Canadian residents
• Why the CRA and IRS classify LLCs differently – and how it can lead to double taxation
• How "disregarded entities" work in the U.S. and why Canada doesn't recognize them the same way
• The hidden reporting requirements, including Form 5472 and Canadian foreign disclosure filings
• How missed foreign disclosure filings can trigger severe cross-border penalties
• The impact of post-2018 U.S. tax rules on non-U.S. LLC owners
• Structuring strategies, including blocker corporations, to reduce cross-border tax friction
• How the Canada-U.S. Tax Treaty can lower withholding taxes when structured properly
This Episode Is Essential To View For:
✓ Canadians looking to purchase "cheap" US real estate in Florida or elsewhere
✓ Entrepreneurs tempted by low-cost online LLC formation services
✓ Investors who currently own US assets through a single-member LLC
✓ Accountants and advisors looking to understand the risks of cross-border entity mismatches
Key Topics Covered:
• Canada vs. U.S. entity classification rules for LLCs
• The Three Tiers of Classification: Disregarded Entities, Partnerships, and C-Corporations
• Canadian tax treatment of U.S. disregarded entities
• Foreign Disclosure filings (T1134, Form 5472, and related reporting)
• Double taxation risks and foreign tax credit limitations
• Post-2018 U.S. tax law changes affecting non-U.S. owners
• Cross-border corporate structuring and blocker corporations
• Canada-U.S. Tax Treaty planning and withholding tax reduction
• Compliance risks and penalty exposure in cross-border structure
Full Transcript
📝 Related Articles

Do You Need A Holding Company In Canada? The 5 Signs
A holding company can save hundreds of thousands in tax – or add needless complexity. Learn the five signs it makes sense, from surplus cash and investments to asset protection and business sales.

The RRSP Trap: Why CRA Takes 54% Of Your RRSP When You Die (And How To Stop It)
A $1 million RRSP can trigger a $540,000 tax bill at death. Learn the little-known strategy that can legally reduce that tax burden and preserve more wealth for your family.
CRA's New Audit Powers — 2026 Update: What's Dropped, What's Still Coming
CRA's New Audit Powers — 2026 Update: What's Dropped, What's Still Coming
Update: the CRA's most-feared new power — compelling answers under oath — was dropped from Bill C-31, and the rest aren't law yet. Here's what's actually proposed (notice of non-compliance, a 10% penalty, stop-the-clock) and what the CRA can already do today.
Need more than a podcast? Cedar Group handles tax planning, restructuring, and sale-readiness advisory for founders.
CEDARGROUP.CA →