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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1,423 guides

Cross-Border Tax (U.S.–Canada)

Roth Conversions Before a Move to Canada: Why the Window Closes at the Border, and How to Size One

September 18, 2026

Converting a traditional IRA to a Roth is a US-resident's decision that becomes a Canadian-resident's problem the day after the move: a conversion made while resident in Canada is a Canadian contribution that taints the Roth's treaty protection and is taxable in Canada as well as the US. Conversions belong before the border — sized to the US brackets of the final US years, and paid from outside the account. Here is the analysis and the sequence.

Cross-Border Tax (U.S.–Canada)

RRSP and 401(k) Compared: Contribution Rules, Treaty Treatment, and What Each Becomes When You Cross the Border

September 18, 2026

The RRSP and the 401(k) are cousins — tax-deferred retirement accounts funded from earned income — and the cross-border mover treats them as interchangeable at their peril. Contribution mechanics, employer involvement, withdrawal rules, and the treaty's treatment of each in the other country differ in ways that decide whether to keep, collapse, or transfer. Here is the side-by-side, and what each account turns into after a move.

Cross-Border Tax (U.S.–Canada)

The Section 962 Election for a US Citizen Who Owns a Canadian Corporation: Corporate Rates on GILTI, and the Dividend Catch Later

September 18, 2026

An individual US shareholder of a Canadian corporation is taxed on its tested income at individual rates with no foreign tax credit for the corporation's Canadian tax — the worst of both worlds. Section 962 lets the individual elect to be taxed as if a corporation on those inclusions: corporate rate, the participation-style deduction, and a credit for the corporation's taxes. The price is paid when the earnings come out. Here is the election, its arithmetic, and who should make it.

Cross-Border Tax (U.S.–Canada)

Sell the Canadian Business Before You Move or After? The Capital Gains Exemption, the CFC Rules, and the Answer That Depends on the Buyer

September 18, 2026

A business owner moving to the US with a sale in view faces a timing decision worth six or seven figures: sell as a Canadian resident and use the lifetime capital gains exemption, or sell after the move and face departure tax on the shares, US tax on the gain, and a year or more inside the CFC regime. The clean answer is usually 'before' — unless the buyer, the deal structure, or the exemption's qualification tests say otherwise. Here is the analysis.

Cross-Border Tax (U.S.–Canada)

Selling a Short-Term Rental You Ran From Across the Border: Recapture, Withholding, Lodging-Tax Close-Out, and the Order to Do It In

September 18, 2026

A cross-border short-term rental exits through more regimes than it entered: depreciation recapture in the country that allowed it, capital gains in both, FIRPTA or section 116 withholding for the non-resident seller, a possible GST/HST hit on a heavily rented Canadian property, and the lodging-tax and platform accounts that have to be closed properly. The order matters — several steps must precede the listing. Here is the exit checklist, both directions.

Cross-Border Tax (U.S.–Canada)

Structuring an E-2 Business as a Canadian: Why the LLC Fails Twice and the C Corporation Usually Wins

September 18, 2026

The E-2 treaty investor visa requires a real US business you own and direct — and the entity you form for it decides your tax life on both sides of the border. Immigration lawyers default to the LLC; for a Canadian who remains connected to Canada, that default creates a corporation-to-Canada mismatch and a self-employment tax bill. Here is how the LLC and C corporation compare for the E-2 investor, and the residency question that decides between them.

Cross-Border Tax (U.S.–Canada)

Subpart F Inside a Canadian Corporation: The Passive Income the IRS Taxes Immediately, and How It Differs From GILTI

September 18, 2026

A US citizen who controls a Canadian corporation has two anti-deferral regimes running at once: Subpart F, which taxes the corporation's passive income to the shareholder in the year earned, and the tested-income regime that reaches the rest. For most Canadian operating companies, Subpart F is the smaller problem — until the retained earnings get invested. Here is what Subpart F catches, the high-tax exception that usually turns it off, and how it fits beside the other regime.

Cross-Border Tax (U.S.–Canada)

TFSA and Roth IRA: Look-Alike Accounts That Each Country Refuses to Recognize From the Other

September 18, 2026

The TFSA and the Roth IRA are the same idea — after-tax contributions, tax-free growth, tax-free withdrawals — implemented by two countries that don't honor each other's version. A Canadian's TFSA is a taxable account to the IRS; an American's Roth IRA is protected in Canada only by a treaty election most people never file. Here is how each account is treated by the other country, the elections and traps, and what a mover should do with each.

Cross-Border Tax (U.S.–Canada)

The 2025 US Tax Law for Canadians With US Income: What Changed for Withholding, Estate Exemptions, and Snowbird Returns

September 18, 2026

The 2025 US tax legislation made the prior individual rate structure permanent, raised the estate and gift exemption to a new permanent level, changed several deductions and reporting thresholds, and — in the version enacted — dropped a proposed surtax on residents of countries with 'discriminatory' taxes that would have hit Canadians directly. For a Canadian with US income or US property, most of the changes are quiet and a few are large. Here is what moved, what didn't, and what to verify.

Cross-Border Tax (U.S.–Canada)

The Canada Child Benefit on a US Return: Not Taxable in Canada, Reportable to the IRS?

September 18, 2026

The Canada Child Benefit is tax-free in Canada by statute — and the American parent receiving it has to decide what it is for US purposes, where no statute says anything. The practitioner consensus treats it as a government social benefit outside gross income, but the reasoning matters, the position should be documented, and the benefit's interaction with the US child tax credit and the joint-election decision is where the real dollars sit. Here is the analysis.

Cross-Border Tax (U.S.–Canada)

The Canada-US Tax Treaty in Plain English: What It Settles, Article by Article, and When You Actually Invoke It

September 18, 2026

Every cross-border tax answer eventually cites 'the treaty,' and almost nobody has read it. The Canada-US Tax Convention is a forty-year-old agreement, amended five times, that decides who is a resident of which country, which country may tax each kind of income, how double taxation is relieved, and how the two tax authorities cooperate. Here is what each article does, in the order a taxpayer meets them, and the handful of moments when you actually invoke one.

Cross-Border Tax (U.S.–Canada)

The Net Investment Income Tax for Americans in Canada: The 3.8% No Foreign Tax Credit Offsets, and the Treaty Argument Over It

September 18, 2026

US citizens in Canada with investment income above the thresholds owe the 3.8% net investment income tax on top of regular US tax — and unlike regular tax, it cannot be reduced by the foreign tax credit under the Code, so Canadian tax already paid on the same income does nothing against it. Practitioners argued the treaty allowed a credit anyway — but in August 2026 the Federal Circuit held that the Canada treaty does not provide one. Here is the tax, why the credit fails, where the treaty argument now stands after that ruling, and the planning that shrinks the base.

Cross-Border Tax (U.S.–Canada)

The RDSP After a Move to the US: Grants Stop, the IRS Sees a Trust, and Whether to Keep It Open

September 18, 2026

The Registered Disability Savings Plan is Canada's most generous savings vehicle — government grants and bonds that can exceed the holder's own contributions — and it depends on Canadian residency in ways the RRSP and TFSA do not: grants and bonds stop when the beneficiary becomes a non-resident, contributions are barred, and the US sees an account it has no treaty provision for. Here is what happens to an RDSP when the family moves, and how to decide whether it stays open.

Cross-Border Tax (U.S.–Canada)

The Section 217 Election on RRSP and Pension Withdrawals: When Filing a Canadian Return Beats Accepting the 25%

September 18, 2026

A non-resident's Canadian pension, RRSP, and RRIF payments are taxed by flat withholding — 25%, or 15% for periodic payments under the treaty — with no return required. Section 217 lets the non-resident file a Canadian return instead and pay graduated rates, which can cut the tax sharply for retirees with modest world income. Here is how the election works, the world-income catch, the NR5 that reduces withholding in advance, and who should use it.

Cross-Border Tax (U.S.–Canada)

The US Child Tax Credit for Families in Canada: Why Claiming the Exclusion Forfeits It, and When the Credit Is Refundable Cash

September 18, 2026

An American family in Canada with children who hold Social Security numbers can receive the US child tax credit — and, because Canadian tax usually zeros their US liability, the refundable portion arrives as a cheque. The catch is the method chosen for the Canadian salary: the foreign earned income exclusion disqualifies the family from the refundable portion; the foreign tax credit preserves it. Here is the credit's rules for families abroad, the exclusion trap, and the annual computation.

Cross-Border Tax (U.S.–Canada)

The Windfall Elimination Provision Is Gone: What Cross-Border Retirees With CPP and Social Security Get Back

September 18, 2026

For decades, a retiree who earned both Canada Pension Plan benefits and US Social Security saw the Social Security reduced under the Windfall Elimination Provision — a formula built for public-sector pensions that swept in foreign ones. The Social Security Fairness Act repealed it, with the Government Pension Offset, for benefits payable from January 2024. Here is what the provision did to cross-border retirees, what repeal restores, who gets retroactive payments, and what still reduces a dual-country benefit.

Cross-Border Tax (U.S.–Canada)

The Windsor-Detroit Commuter: Why Daily Crossings Don't Make You a US Resident, and the Michigan and Ontario Returns You File Instead

September 18, 2026

Thousands of Ontario residents cross to Michigan for work every day — nurses, engineers, auto workers — and the substantial presence test counts every one of those days. They are not US tax residents anyway, because the test has a commuter exception written for exactly them. Here is the exception, the US and Michigan returns the commuter still files, the Canadian side with its foreign tax credit, and the payroll setup that makes the whole arrangement work.

Cross-Border Tax (U.S.–Canada)

Timing CPP and Social Security Together: Start Ages, Survivor Math, and How the Treaty Taxes Each

September 18, 2026

A retiree with credits in both countries has two claiming decisions — CPP from 60 to 70, Social Security from 62 to 70 — and the usual single-country advice (defer as long as you can) doesn't automatically hold when the two are combined, taxed by different countries, and paid in different currencies. Here is how each program's timing arithmetic works, how the treaty assigns the tax on each, and how the two decisions interact.

Cross-Border Tax (U.S.–Canada)

Wash Sales and Superficial Losses: Two Loss-Denial Rules With Different Windows, and the Trade That Trips Both

September 18, 2026

Both countries deny a capital loss when you sell and buy back too soon — the US wash sale rule and Canada's superficial loss rule — but the rules differ in scope (securities versus identical property), in who counts (a spouse and controlled corporation in the US; an expanded affiliated-person list including your own RRSP and TFSA in Canada), in what happens to the denied loss, and in whether crypto is covered. A cross-border investor harvesting losses runs both tests on every trade. Here is the side-by-side.

Cross-Border Tax (U.S.–Canada)

What TFSA Reporting on a US Return Actually Involves, and Why Quotes for It Vary So Much

September 18, 2026

A US citizen with a tax-free savings account gets wildly different quotes for reporting it — because the work ranges from one line on Schedule B to a stack of PFIC forms, a foreign-trust position, and two information returns, depending on what the account holds and how the preparer treats it. Here is the actual work, item by item, why the range is real, and how to shrink it to the small version.

Cross-Border Tax (U.S.–Canada)

Your GST/HST Account After Moving to the US: Deregister, Keep It for Canadian Clients, or Zero-Rate the Exports

September 18, 2026

A registered Canadian freelancer who moves to the US carries an open GST/HST account into non-residency — and the account has three futures: close it (with a final return and a deemed sale of capital property), keep it because you still supply taxable services in Canada, or keep it to zero-rate exports and claim input credits. The right answer depends on where your work is performed and who your clients are. Here is the decision, and the closing mechanics.

Cross-Border Tax (U.S.–Canada)

Your Spouse Owns the Canadian Corporation: When the Form 5471 Attribution Rules Make It Your Filing Too

September 18, 2026

A US citizen married to a Canadian who owns a Canadian corporation often assumes one of two wrong things: that the spouse's shares are irrelevant to the US return, or that the spouse's ownership is automatically attributed to them. The constructive ownership rules give a precise and counterintuitive answer that turns on whether the owning spouse is a US person — and on whether the US spouse holds an office or directorship. Here is how attribution actually runs.

Cross-Border Tax (U.S.–Canada)

After You File Streamlined: What the IRS Does With It, How Long Silence Lasts, and What Would Trigger a Look

September 17, 2026

Streamlined submissions produce no acceptance letter — the returns process, the payment posts, and then nothing. The nothing is the good outcome. Here is what actually happens on the IRS side, how to read your account transcripts for confirmation, the ordinary audit rules that still apply, and the handful of events that would turn a processed submission into an examination.

Cross-Border Tax (U.S.–Canada)

Born Dual, Never Left Canada: The US Return You Owe Anyway, and Why It Usually Shows Zero Tax

September 17, 2026

You were born in Canada to an American parent — or born in the US and brought home as an infant — and you have lived your whole life in Canada. You are a US citizen, and US citizens file US returns wherever they live. Here is what the obligation actually consists of for someone who has never set foot in an American tax system, why the tax is usually nothing, and what the paperwork is not.

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