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Guides · Cross-Border

Cross-Border guides

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

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

How Much Does Cross-Border Bookkeeping Cost for a Canadian with US Income?

Cross-border bookkeeping for a Canadian with US income runs $300 to $2,000/month depending on the number of entities, currencies, and reporting requirements in both countries.

Sep 17, 2026
Cross-Border

How Much Does an ITIN Application Cost for a Canadian?

The IRS charges nothing for the ITIN itself, but the W-7 preparation, CAA certification, and the required tax return add up to $1,000 to $3,000+ for most Canadians.

Sep 17, 2026
Cross-Border

When Does a Canadian Business Create US Tax Nexus? Physical Presence, ECI, and the Treaty Shield

A Canadian business creates US tax nexus when it earns income that is effectively connected with a US trade or business.

Sep 4, 2026
Cross-Border

Canadian CCPC with a US Shareholder: How Integration Breaks and What to Do About It

Canada's corporate integration system is designed so that income earned through a CCPC is taxed at roughly the same rate as income earned personally.

Sep 4, 2026
Cross-Border

Canadian Departure Tax: The Deemed Disposition When You Leave Canada

When a Canadian resident emigrates, Canada treats them as having sold most of their property at fair market value on the date of departure.

Sep 4, 2026
Cross-Border

Moving from Canada to the US: Tax Planning Checklist Before You Cross the Border

A Canadian who is moving to the US should take several tax steps before departure to minimize the departure tax, preserve treaty benefits.

Sep 4, 2026
Cross-Border

The US LLC Tax Trap for Canadians: Why a Disregarded Entity Creates Double Taxation

A Canadian resident who owns a single-member US LLC faces potential double taxation.

Sep 4, 2026
Cross-Border

Canadian RRSP and US Tax: How the US Treats Your Canadian Retirement Account

A US person with a Canadian RRSP faces a mismatch between how Canada and the US treat the account. Canada defers tax on RRSP contributions and growth.

Sep 4, 2026
Cross-Border

Canadian Tax on US Social Security Benefits: How Canada Taxes Your American Retirement Income

A Canadian resident who receives US Social Security benefits reports only 85% on the Canadian return. The treaty and ITA 110(1)(f) determine the actual.

Sep 4, 2026
Cross-Border

Cross-Border Alimony and Child Support: Tax When Payments Cross the Canada-US Border

Alimony paid across the border is taxed differently in each country. Since 2019, US alimony is neither deductible nor taxable.

Sep 4, 2026
Cross-Border

Cross-Border Business Structures: Comparing Options for Operating in Both Canada and the US

A cross-border business must choose between an LLC, a corporation, and a branch. Each produces different tax consequences in Canada and the US.

Sep 4, 2026
Cross-Border

Selling a Cross-Border Business: Tax on the Sale When Owner and Company Span Canada and the US

A share sale, asset sale, or earn-out each produce different tax results in Canada and the US. Treaty credits limit but do not eliminate double tax.

Sep 4, 2026
Cross-Border

Cross-Border Charitable Donations: Tax Deductions When You Give Across the Canada-US Border

A Canadian can deduct US charity donations only against US-source income. US persons face the same cap on gifts to Canadian charities under Article XXI.

Sep 4, 2026
Cross-Border

Cryptocurrency Tax for Cross-Border Canadians and Americans: How Both Countries Tax Crypto

Both Canada and the US tax cryptocurrency dispositions as capital events. Cross-border holders face additional reporting on foreign exchanges, FBAR.

Sep 4, 2026
Cross-Border

Cross-Border Divorce: Tax Consequences of Property Division Between Canada and the US

When spouses in a cross-border marriage separate and divide property, both countries may tax the transfers.

Sep 4, 2026
Cross-Border

Cross-Border Estate and Inheritance Tax: What Happens When Assets and Heirs Are in Different Countries

The US imposes estate tax on worldwide assets of US persons and on US-situs assets of non-residents. Canada taxes gains at death through deemed.

Sep 4, 2026
Cross-Border

Cross-Border Estate Planning for Canadians and Americans: How to Avoid Double Taxation at Death

When a person with assets in both Canada and the US dies, two countries can tax the same estate. Canada taxes deemed dispositions; the US taxes the estate.

Sep 4, 2026
Cross-Border

Cross-Border Gift Tax: How Canada and the US Tax Gifts Between Family Members in Different Countries

The US imposes a gift tax on the donor. Canada and the US handle gifts in fundamentally different ways. Canada has no gift tax.

Sep 4, 2026
Cross-Border

Cross-Border Medical Expenses: Tax Deductions for Healthcare Costs Paid in the Other Country

Medical expenses paid in the US by a Canadian resident and healthcare costs paid in Canada by a US person are deductible in the taxpayer's country.

Sep 4, 2026
Cross-Border

Cross-Border Rental Property: Tax When a Canadian Owns US Real Estate (or Vice Versa)

Owning rental property across the Canada-US border creates filing obligations in both countries. Each country taxes the income and requires specific forms.

Sep 4, 2026
Cross-Border

Cross-Border Rental Property: Tax Rules for Canadians Renting US Property and Americans Renting Canadian Property

Owning rental property in the other country creates filing obligations in both Canada and the US.

Sep 4, 2026
Cross-Border

Cross-Border Retirement Withdrawals: Tax on RRSP, 401(k), IRA, and Pension When You Live in the Other Country

Withdrawing from a retirement account in one country while living in the other triggers withholding, income inclusion, and a foreign tax credit.

Sep 4, 2026
Cross-Border

Stock Options When You Relocate Between Canada and the US: Who Taxes What

An employee who relocates between Canada and the US while holding unvested stock options faces one of the more complex cross-border tax problems.

Sep 4, 2026
Cross-Border

Cross-Border Stock Options and RSU Taxation: How Canada and the US Tax Your Equity Compensation

Employees who work in both Canada and the US, or who move between the two countries while holding unvested stock options or RSUs.

Sep 4, 2026