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Guides · Cross-Border

Cross-Border guides

581 plain-English guides on cross-border, each one ending in what to do next.

All Cross-BorderUS TaxCanadian TaxSmall Business & BookkeepingCFO & AdvisoryTax Planning

Page 16 of 25, newest first.

Cross-Border

Your Child Was Born in Canada to a US Citizen Parent: Tax Obligations

If one parent is a US citizen (or in some cases a US national or long-term resident), a child born in Canada is a US citizen at birth under INA 301.

Aug 30, 2026
Cross-Border

US Tax Filing Deadlines for Americans in Canada

The Canadian T1 return is due April 30 (June 15 if you or your spouse is self-employed, but the balance owing is still due April 30).

Aug 30, 2026
Cross-Border

W-8BEN-E: When a Canadian Corporation Earns US-Source Income

A Canadian corporation receiving US-source payments (dividends, royalties, service fees) files Form W-8BEN-E to claim treaty-reduced withholding rates.

Aug 30, 2026
Cross-Border

W-4 Withholding for Cross-Border Workers: Canadian Working in the US

The W-4 doesn't ask about your Canadian situation, but your Canadian situation changes what the right W-4 looks like. Here is how to set it up.

Aug 30, 2026
Cross-Border

When Does a Canadian Need to File a US Tax Return?

Canadians file US tax returns for one of four reasons: they hold US citizenship (including accidental Americans who have never lived in the US).

Aug 30, 2026
Cross-Border

Year-End Tax Planning for Cross-Border Filers: Canada-US Checklist

Cross-border filers have year-end planning opportunities in both countries, and the deadlines do not always align.

Aug 30, 2026
Cross-Border

The 14-Day Rule for a Canadian's Florida Condo

Section 280A classifies your Florida condo as full rental, mixed use, or personal residence based on the 14-day and 10% thresholds.

Aug 27, 2026
Cross-Border

My bank closed my account because of FATCA. Now what?

Canadian and European banks are closing accounts over FATCA when a customer can't produce a US Social Security number.

Aug 27, 2026
Cross-Border

I'm apparently a US citizen and I've never filed. Now what?

Your bank asked for a US place of birth or a US parent on a form you filled out without thinking twice.

Aug 27, 2026
Cross-Border

Does Managing My US Airbnb Make Me a US Tax Resident?

Active Airbnb management won't change your day count, but it can move your tax home to the US, kill the closer connection exception.

Aug 27, 2026
Cross-Border

Airbnb Tax Withholding for Non-US Property Owners

How Airbnb and Vrbo withhold US tax from non-resident property owners, the difference between W-8BEN and W-8ECI.

Aug 27, 2026
Cross-Border

Bare trust reporting in Canada: the T3 rules

Canada now requires T3 filings for bare trusts worth over $50,000. Here's who has to file, what the penalties are, and how US persons get caught twice.

Aug 27, 2026
Cross-Border

Both Countries Auditing the Same Income: What Happens and Who Goes First

The CRA and the IRS exchange information under Article XXVII of the Canada-US tax treaty, and an audit in one country can trigger an audit in the other.

Aug 27, 2026
Cross-Border

Canadian Buying a US Vacation Rental: How Should I Hold It?

How you hold a US vacation rental affects cost segregation, platform withholding, passive activity grouping, estate tax, and Canadian reporting.

Aug 27, 2026
Cross-Border

Competent Authority and the Mutual Agreement Procedure (US-Canada Treaty)

When both countries tax the same income and the treaty does not fix it. But some disputes cannot be resolved that way.

Aug 27, 2026
Cross-Border

Cross-Border Charitable Giving: Strategies for Donors Who File in Both Canada and the US

Give listed shares in kind, use charities recognized on both sides, and plan 2026 US returns around the 0.5% floor.

Aug 27, 2026
Cross-Border

Cross-Border Penalty Coordination: Owing Penalties in Both Countries

Owing penalties to both the IRS and CRA at the same time. If you filed your Canadian return late, you owe the CRA a late-filing penalty.

Aug 27, 2026
Cross-Border

Cross-border power of attorney for tax matters

If you live in one country and have tax obligations in the other, a single power of attorney won't cover you.

Aug 27, 2026
Cross-Border

Deceased Parent's CRA/IRS Debt: What the Estate and the Kids Owe

The short answer: the estate pays, not the children, unless the children received assets from the estate before the tax debt was settled.

Aug 27, 2026
Cross-Border

Deemed disposition on death in Canada vs US stepped-up basis

When a Canadian resident dies, Canada taxes every dollar of unrealized capital gain as if the person sold everything the day before death.

Aug 27, 2026
Cross-Border

DIIRSP: The IRS Procedure for Late International Information Returns

If your income tax returns were filed on time and the only thing missing is a form, one for your Canadian corporation, your TFSA.

Aug 27, 2026
Cross-Border

Executor liability in cross-border estates: Canada and US exposure

If you're the executor (or liquidator, in Quebec) of a cross-border estate, you've inherited a job with personal financial risk.

Aug 27, 2026
Cross-Border

Foreign Accrual Property Income (FAPI): How Canada Taxes Your US Corporation Before You Take a Dividend

The two regimes look alike from a distance and behave very differently up close, and the difference is where the money is lost.

Aug 27, 2026
Cross-Border

FIRPTA and Cost Segregation Recapture on a Vacation Rental Sale

Cost segregation on a vacation rental triggers IRC 1245 ordinary recapture on sale, and FIRPTA withholding at closing may not cover the actual tax bill.

Aug 27, 2026