Guides

Straight answers, written by the people who’d file it.

1,423 plain-English guides on cross-border moves, US and Canadian returns, and small-business money. Each one ends in what to do next, and says when a written Position Check is the smarter first step.

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CROSS-BORDER A Canadian Corporation With a U.S. Shareholder

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Fairlight Accounting · US + Canadian Tax Desks

1,423 guides

Cross-Border Tax (U.S.–Canada)

Winning in the Other Country: How Canada and the US Tax Gambling and Lottery Winnings Across the Border

September 7, 2026

Canada does not tax casual gambling winnings. The US taxes them at 30% withholding for non-residents. A Canadian who wins in the US can recover some or all of the US tax by deducting losses under the treaty; an American who wins in Canada owes the IRS on it anyway.

Cross-Border Tax (U.S.–Canada)

Getting Married Across the Border: Filing Status, the Joint-Return Election, and What Each Country Does With a Foreign Spouse

September 7, 2026

Marriage changes your filing status, opens (or closes) elections, and creates new reporting obligations in both countries. Here is what changes on the tax side when a Canadian marries a US person, or when a couple ends up on opposite sides of the border.

Cross-Border Tax (U.S.–Canada)

The Green Card Holder Living in Canada: A US Resident for Tax Purposes Wherever You Are

September 7, 2026

What a US green card holder owes when living in Canada: the worldwide filing obligation, FBAR, Form 8938, the treaty tie-breaker and its immigration and expatriation risks, and the abandonment decision.

Cross-Border Tax (U.S.–Canada)

H-1B and L-1 in the First US Year: The Dual-Status Math, the Full-Year Election, and the Canadian Bonus Paid After You Left

September 7, 2026

The US tax filing for Canadians arriving on H-1B or L-1 visas: how the substantial presence test sets the residency start date, when the dual-status return beats the full-year election, how FICA applies from the first paycheque, and what happens to Canadian income that arrives after the move.

Cross-Border Tax (U.S.–Canada)

I Haven't Filed US Taxes in Years. How Far Back Do I Go? Three Returns and Six FBARs Under Streamlined, or Six Years Outside It

September 7, 2026

A US person who has not filed for years does not file every year back to the beginning. The streamlined procedures require three years of returns and six years of FBARs; outside the program, the IRS's own policy asks for six years of returns. Here is what governs the lookback, what stays open forever, and how to choose.

Cross-Border Tax (U.S.–Canada)

The Home Office Across the Border: What Canada Lets You Deduct, What the US Doesn't, and the Remote Worker in the Middle

September 7, 2026

How to claim home office expenses when you work from home across the Canada-US border: Canada's detailed method with Form T2200 for employees and business-use-of-home for the self-employed; the US rule that employees get nothing and the self-employed choose between simplified and actual; and the complications for a remote worker taxed in both.

Cross-Border Tax (U.S.–Canada)

What Drives the Cost of a Cross-Border Tax Return, and Why Two Files With the Same Income Can Differ by Multiples

September 7, 2026

Cross-border returns cost more than domestic ones. Here is what drives the price: the number of returns, the forms each account triggers, the departure-year work, and whether the file is current or a catch-up. Fairlight's pricing is published; this explains the ranges.

Cross-Border Tax (U.S.–Canada)

Reporting Canadian Income on a US Return: Where Each Slip Goes, Which Rate to Use, and the Mistakes That Trigger Letters

September 7, 2026

A practical guide to converting T4, T4A, T3, T5, T5008, T4A(P), T4A(OAS), T4RSP, and NR4 slips into 1040 line items: where each type goes, which exchange rate to use, how Canadian dividends and capital gains are characterized, and the common mistakes.

Cross-Border Tax (U.S.–Canada)

Income Splitting Across the Border: What Canada Allows, What the US Allows, and What Stops Working When a Spouse Moves

September 7, 2026

How income splitting works in Canada and the US, and what changes when you are a cross-border taxpayer: pension splitting, spousal RRSPs, TOSI, prescribed-rate loans, joint filing, and the coordination when spouses are resident in different countries.

Cross-Border Tax (U.S.–Canada)

Incorporating Across the Border: Canadian Corporation, US C Corporation, LLC, or ULC, and Why the Owner's Residence Decides

September 7, 2026

Where to incorporate when you live in one country and do business in both. Canadian corporation, US LLC, US C corporation, and the unlimited liability company, and the cross-border tax traps that follow each choice. The owner's residence, not the customers' location, is the deciding factor.

Cross-Border Tax (U.S.–Canada)

IRA and Roth IRA Contributions for Americans in Canada: Why the FEIE Blocks Them and Why the Roth Gets Tainted

September 7, 2026

Can an American living in Canada contribute to an IRA or Roth IRA? Yes, if there is taxable compensation not excluded by the FEIE. But the Roth election under the treaty is lost by contributions made as a Canadian resident, and the RRSP is usually the better vehicle.

Cross-Border Tax (U.S.–Canada)

Late-Filing Penalties on Both Sides of the Border: What the IRS and CRA Charge, and the Information-Return Penalties That Dwarf Them

September 7, 2026

How the IRS and CRA penalize late filing and late payment, and, more importantly for cross-border filers, the penalties on information returns (FBAR, Forms 3520, 5471, 8938, T1135) that apply even when no tax is owed and can exceed the tax by multiples.

Cross-Border Tax (U.S.–Canada)

Is 30% Really Taken Off My US Rental Income, or Can I Elect Out of It? Yes, and Yes: The Section 871(d) Election

September 7, 2026

By default the US taxes a non-resident's rental income at 30% of gross rent, with no deductions, through withholding. The section 871(d) election replaces that with tax on net income at graduated rates. Here is how the election works, how to make it, what it requires every year after, and how to recover withholding from before you made it.

Cross-Border Tax (U.S.–Canada)

J-1 Visa Tax for Canadians in the US: Exempt Individual Status and the Canadian Residency That Continues

September 7, 2026

How a Canadian on a J-1 visa (research scholar, trainee, intern, teacher, camp counsellor, summer work travel) is taxed in the US and Canada: exempt individual status, the 1040-NR, FICA exemption, and why most J-1 Canadians remain Canadian tax residents throughout.

Cross-Border Tax (U.S.–Canada)

Joint Accounts Across the Border: Who Reports What on the FBAR, the T1135, and the Estate Return

September 7, 2026

Joint accounts between spouses, or with a parent or child, create reporting obligations on both sides. The US person reports the full balance on the FBAR; Canada attributes income to whoever funded the account; and at death, the US estate rules on joint property can include the full value in the wrong estate.

Cross-Border Tax (U.S.–Canada)

Keeping Canadian Bank Accounts After Moving to the US: What Works, What Gets Restricted, and What to Report

September 7, 2026

You can keep your Canadian bank accounts after moving to the US, and usually should. Here is what happens to each account type, what Canadian institutions will and will not do for a US resident, and the reporting you take on.

Cross-Border Tax (U.S.–Canada)

Maternity and Parental Benefits Across the Border: EI and QPIP for a Parent in the US, and US State Leave for a Parent in Canada

September 7, 2026

How EI maternity and parental benefits and QPIP are taxed when a parent moves to the US during leave, how US state paid family leave is taxed for a Canadian resident, and the eligibility rules that decide whether the benefits continue at all.

Cross-Border Tax (U.S.–Canada)

Medical Expenses Across the Border: Canada's Credit, the US Deduction, and the Treatment Paid for in the Other Country

September 7, 2026

How medical expenses work in Canada (a credit above a 3% threshold) and the US (an itemized deduction above 7.5% of AGI), whether expenses paid in the other country qualify, and how cross-border families with private insurance, US treatment, or Canadian premiums handle both.

Cross-Border Tax (U.S.–Canada)

Mortgage Interest Across the Border: Not Deductible in Canada, Deductible in the US, and the Rental Exception That Works in Both

September 7, 2026

Mortgage interest on a principal residence is not deductible in Canada but is deductible in the US up to $750,000 of acquisition debt. Here is what that means for an American in Canada, a Canadian in the US, and the rental property that gets the deduction in both.

Cross-Border Tax (U.S.–Canada)

Moving Back to Canada and Still Own a Place in Florida: Should I Sell Before I Go? The Section 121 Window and the Canadian Cost Reset

September 7, 2026

A US resident returning to Canada with a Florida home faces a choice with a clock on it: sell as a US resident and use the Section 121 exclusion, or keep it and face US non-resident rental rules, FIRPTA, and a Canadian gain measured from the arrival-date value. Here is the timing math.

Cross-Border Tax (U.S.–Canada)

Moving Expenses Across the Border: Why Neither Country Deducts Them, and How Employer Reimbursements Are Taxed Differently

September 7, 2026

Moving expenses are no longer deductible in the US except for the military, and in Canada only for moves within Canada. A cross-border move gets no deduction on either side, and employer reimbursements are taxable in the US but not in Canada. Here is the detail.

Cross-Border Tax (U.S.–Canada)

How Do I Write a Non-Willfulness Certification the IRS Will Actually Accept? Specific Facts, Not Boilerplate

September 7, 2026

Form 14653 (or 14654) is the heart of a streamlined submission. The IRS reads the narrative and rejects certifications that are generic, inconsistent with the returns, or that describe willful conduct. Here is what a certification must contain, the facts that support non-willfulness, the facts that undermine it, and how to structure the narrative.

Cross-Border Tax (U.S.–Canada)

NR301: The Form That Cuts Canadian Withholding From 25% to the Treaty Rate, and the NR7-R That Recovers It When You Forgot

September 7, 2026

How non-residents claim treaty benefits on Canadian-source income using NR301 (and NR302 and NR303 for partnerships and hybrids), which income types it covers, how long it is valid, and how to recover over-withheld tax when it was not on file.

Cross-Border Tax (U.S.–Canada)

The OAS Clawback for Non-Residents: Why US Residents Escape It and Residents of Other Countries Don't

September 7, 2026

Old Age Security is subject to a recovery tax ('clawback') above an income threshold. For non-residents, the CRA collects it through the Old Age Security Return of Income, but the Canada-US treaty makes OAS taxable only in the US, so US residents are exempt. Here is how it works for cross-border retirees.

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