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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 18 of 25, newest first.

Cross-Border

Streamlined Filing for Self-Employed and Business Owners

Self-employment makes streamlined filing harder and costlier: Schedule C, SE tax in arrears, estimated tax penalties that survive, Form 5471, QBI.

Aug 27, 2026
Cross-Border

State Tax After Streamlined Filing: What the IRS Program Doesn't Cover

You filed the streamlined package. Three years of federal returns, six years of FBARs, the certification, maybe the 5% penalty check.

Aug 27, 2026
Cross-Border

What Is the Streamlined Foreign Offshore Procedure, and Do I Actually Qualify?

SFOP clears five IRS penalty categories for qualifying non-willful citizens and green card holders abroad.

Aug 27, 2026
Cross-Border

I Have a Green Card and Live in Canada. Can I Use Streamlined to Catch Up on US Taxes?

Usually yes, but the green card raises a second question streamlined alone doesn't answer: are you still a US tax resident, and do you want to be?

Aug 27, 2026
Cross-Border

How do I write a non-willfulness certification the IRS will actually accept?

The non-willfulness certification, Form 14653 if you live outside the United States, Form 14654 if you live inside it.

Aug 27, 2026
Cross-Border

Streamlined vs. Voluntary Disclosure: When Willfulness Changes the Calculus

The IRS Streamlined Filing Compliance Procedures are the most commonly recommended path for US persons who are behind on their offshore reporting.

Aug 27, 2026
Cross-Border

Streamlined Filing With PFICs: Canadian Mutual Funds

Canadian mutual funds are PFICs, RRSP and TFSA holdings included, and each needs its own Form 8621 every covered year.

Aug 27, 2026
Cross-Border

Testamentary trusts after 2016: GRE and QDT rules in Canada

A testamentary trust is any trust that arises on (and because of) a person's death, typically created by a will.

Aug 27, 2026
Cross-Border

US Estate Tax on a Canadian's Florida Vacation Rental

US real property is a US-situs asset for estate tax purposes, and the $60,000 NRA exemption covers almost nothing.

Aug 27, 2026
Cross-Border

My US LLC Is Now on Airbnb. What Changed for Canadian Tax?

Listing a US LLC on Airbnb changes the trade-or-business classification, withholding, and FAPI on the Canadian side.

Aug 27, 2026
Cross-Border

US person as trustee of a Canadian trust: the tax complications

A US citizen or green card holder as trustee can change a Canadian trust's US classification, trigger annual reporting.

Aug 27, 2026
Cross-Border

Wash sale vs superficial loss: cross-border guide

How the US wash sale rule and Canada's superficial loss rule interact for cross-border investors harvesting tax losses across both countries.

Aug 27, 2026
Cross-Border

CRA T1135 Penalties: Missed Foreign Property Reporting and How to Fix It

The penalties apply even if you reported all the income from those accounts on your return and owe zero additional tax.

Aug 26, 2026
Cross-Border

CRA VDP for Cross-Border Filers: Coordinating with IRS Streamlined

If you are a US person with Canadian filing obligations (or a Canadian resident with US filing obligations) and you are behind on both sides.

Aug 26, 2026
Cross-Border

FBAR Penalties: The Decision Tree

The wrong route can turn a zero-penalty fix into a six-figure bill, and the right route can take a potential $100,000+ exposure and resolve it for nothing.

Aug 26, 2026
Cross-Border

Form 3520 Penalty Abatement: The Policy Change and What It Means

The IRS changed how it handles Form 3520 penalties in late 2024. What this means for TFSA, RESP, and foreign trust penalties, and how to request abatement.

Aug 26, 2026
Cross-Border

Form 5471 and 5472 Penalties: Abatement Paths After the Tax Court Rulings

The penalties are designed for large multinationals hiding offshore income, but they land equally on dual citizens running a one-person Canadian company.

Aug 26, 2026
Cross-Border

Leaving Canada for Australia: What's the Tax Picture?

The complete tax checklist for Canadians moving to Australia permanently. Australia has no mirror arrival tax.

Aug 26, 2026
Cross-Border

Leaving Canada for Dubai: What's the Tax Picture?

Tax checklist for Canadians moving to Dubai or the UAE. Departure tax, RRSP, TFSA, pensions, Part XIII withholding without a treaty cap, and Section 217.

Aug 26, 2026
Cross-Border

Leaving Canada for Mexico: What's the Tax Picture?

Tax checklist for Canadians moving to Mexico. Departure tax, RRSP, TFSA, pensions, the Canada-Mexico treaty step-up election, and SAT registration.

Aug 26, 2026
Cross-Border

Leaving Canada for Portugal: What's the Tax Picture?

The tax checklist for Canadians moving to Portugal. Departure tax, RRSP, TFSA, pensions, the Canada-Portugal treaty, and what replaced the NHR regime.

Aug 26, 2026
Cross-Border

Leaving Canada for the UK: What's the Tax Picture?

The tax checklist for Canadians moving to the UK. Departure tax, RRSP, TFSA, pensions, the Canada-UK treaty, and the Statutory Residence Test.

Aug 26, 2026
Cross-Border

Do I Send a 1099 to a Canadian Contractor?

US businesses do not issue a 1099 to Canadian contractors who provide a W-8BEN. The W-8BEN claims the treaty exemption and eliminates US withholding.

Aug 24, 2026
Cross-Border

Can Americans Buy Property in Canada? Rules, Taxes, and the Foreign Buyer Ban

Americans can buy Canadian property, but a federal ban on foreign residential purchases runs through January 2027.

Aug 24, 2026