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Guides · Cross-Border

Cross-Border guides

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

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

Page 17 of 26, newest first.

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. Covers treaty provisions, foreign tax.

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. Covers key rules, filing.

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, and now it wants a Social Security number you.

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. Covers key rules, filing requirements,.

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.

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. Covers key rules, filing.

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. Covers treaty provisions, foreign tax.

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. The reverse is equally true.

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
Cross-Border

Form 706-NA: filing the US estate tax return for a Canadian who died owning US assets

A Canadian dies owning a Florida condo and a brokerage account holding US shares. Nine months later the IRS expects a return.

Aug 27, 2026
Cross-Border

I Haven't Filed US Taxes in Years. How Far Back Do I Go?

The IRS does not want fifteen years of back returns. It wants three years of income tax returns and six years of FBARs, filed through the right program.

Aug 27, 2026
Cross-Border

What Is an In-Trust-For (ITF) Account and How Is It Taxed?

An ITF account at a Canadian bank looks simple but triggers Canadian attribution rules, plus foreign trust reporting when a parent or child is a US person.

Aug 27, 2026
Cross-Border

Joint tenancy (JTWROS) across the border: Canada and US tax traps

The tax consequences aren't simple at all, and they get worse when one of those names belongs to a US citizen or green card holder.

Aug 27, 2026