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Guides · Cross-Border

Cross-Border guides

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

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

Page 20 of 26, newest first.

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. Covers key rules, filing.

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. Covers treaty provisions, foreign.

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. Covers key rules, filing requirements,.

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. Covers treaty provisions, foreign tax.

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. Compare LLC, S-Corp, and sole.

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. Covers treaty provisions, foreign.

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

T1135 Late Filing Penalty: Amounts, Relief and the VDP

The T1135 late filing penalty is $25 a day up to $2,500 per form, even with no tax owing. Gross negligence adds more. Here's how relief and the 2025 VDP rules work.

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: Amounts, Bittner and the Decision Tree

FBAR penalties run up to $16,536 per report non-willful and the greater of $165,353 or 50% per account willful. How the IRS sets the amount, and which route fits your facts.

Aug 26, 2026
Cross-Border

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

The IRS now considers reasonable cause statements on late Forms 3520 and 3520-A before assessing a penalty. What that means for TFSA, RESP and gift penalties, and 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?

Leaving Canada for Australia triggers departure tax on unrealized gains. Australia has no arrival tax, and a cost-base step-up stops double tax on the gain.

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? Yes, With Limits

Yes, Americans can own Canadian property, but a federal ban on buying homes in urban areas runs to January 1, 2027, and BC and Ontario add 20% to 25% foreign buyer taxes.

Aug 24, 2026
Cross-Border

Canadian Citizenship by Descent: Who Qualifies and What It Means for Your Taxes

If you were born outside Canada to a Canadian parent, you may already be a Canadian citizen by descent. Under the Citizenship Act.

Aug 24, 2026
Cross-Border

Do US Citizens Pay Double Taxes When Living in Canada?

US citizens in Canada file two returns but rarely pay two full tax bills. The short answer is no, not on most income. Covers key rules, filing.

Aug 24, 2026
Cross-Border

EIN Number in Canada: The BN Equivalent and How to Apply

Canada's version of an EIN is the CRA business number (BN). A Canadian company that needs a US EIN files Form SS-4 by phone, fax or mail, pays no fee, and can get it on the call.

Aug 24, 2026
Cross-Border

FATCA Explained: What the Foreign Account Tax Compliance Act Means for You

FATCA requires foreign banks to report accounts held by US persons to the IRS and requires US persons to report foreign financial assets on Form 8938.

Aug 24, 2026