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.

Capital gains RRSP TFSA Departure tax Estate tax FBAR LLC Principal residence

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

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1,423 guides

Cross-Border Tax (U.S.–Canada)

The Arrival Step-Up: Canada Resets Your Cost Basis the Day You Move — the US Does Not, and the Gap Is a Planning Window

September 14, 2026

On becoming a Canadian resident you are deemed to acquire your property at fair market value — Canada will only ever tax appreciation from that day. The US keeps your historic basis. That mismatch makes the weeks before the move a one-time window to realize gains US-only, and it creates two permanent basis ledgers for everything you keep. Here is how to use it.

Cross-Border Tax (U.S.–Canada)

The Best US Entity for a Canadian Owner: Why the LLC Everyone Recommends Is the One Structure to Avoid

September 14, 2026

Every US advisor's default — the LLC — is the worst wrapper a Canadian can own, because Canada sees a corporation where the US sees a flow-through and the mismatch double-taxes distributions. The structures that actually work for Canadians are the limited partnership, the US C corporation, and sometimes nothing at all. Here is the entity menu re-ranked for a Canadian passport.

Cross-Border Tax (U.S.–Canada)

Breaking US State Residency When You Move to Canada: Why the State Is Harder to Leave Than the Country

September 14, 2026

The IRS follows you to Canada by design; your state is supposed to let go — and the sticky states often don't. Domicile rules, statutory residency day counts, and aggressive audit programs in states like California and New York can keep state tax alive years after the move. Here is how state residency actually ends, and the evidence file that ends it.

Cross-Border Tax (U.S.–Canada)

A Canadian Amazon FBA Seller's US Taxes: What the Warehouse Inventory Does and Doesn't Change

September 14, 2026

FBA puts your inventory in American warehouses, and every forum thread says that changes everything. The truth is split: marketplace rules now handle most state sales tax, the income-tax answer runs through the treaty's permanent establishment test where third-party fulfillment inventory presents a genuinely debated question, and the professional posture is the protective return. Here is the FBA seller's actual map.

Cross-Border Tax (U.S.–Canada)

A Canadian Business Selling Into the US: When American Customers Create American Tax — and the Three Different Nexus Rules That Decide

September 14, 2026

Selling to US customers does not by itself make a Canadian company a US taxpayer: federal income tax needs a permanent establishment under the treaty, states run their own economic nexus rules the treaty does not bind, and sales tax nexus triggers on thresholds alone. Three rulebooks, three answers. Here is the map, plus the protective filing that guards the treaty position.

Cross-Border Tax (U.S.–Canada)

A Canadian Company Hiring US Contractors: What You Withhold (Usually Nothing), What You File, and Where the Real Risks Sit

September 14, 2026

Paying an American contractor who works from the US is refreshingly clean for a Canadian payer: no Canadian withholding on services performed outside Canada, no T4A-NR, no US information return for the foreign payer in the standard case. The risks live elsewhere — the contractor who visits Canada, the one who is really an employee, and the paperwork that proves the clean case. Here is the employer-side map.

Cross-Border Tax (U.S.–Canada)

Your Canadian Corporation After You Move to the US: CCPC Status Lost, CFC Status Gained, and the Windows That Close at Departure

September 14, 2026

Move to the US owning a Canadian company and the company changes twice without a single document: it stops being a Canadian-controlled private corporation (goodbye small business deduction and capital gains exemption) and becomes a controlled foreign corporation to the IRS (hello Form 5471 and GILTI). Here is what happens, what it costs, and the pre-departure moves that matter.

Cross-Border Tax (U.S.–Canada)

Keeping Canadian Investment Accounts After Moving to the US: the Broker Problem, the PFIC Problem, and the Pre-Move Cleanup

September 14, 2026

A Canadian taxable account can technically follow you to the US — but most Canadian brokerages restrict US-resident clients, every Canadian mutual fund and ETF in the account becomes a PFIC on your 1040, and the departure tax has already reset your Canadian side. Here is the account triage that should happen before the flight.

Cross-Border Tax (U.S.–Canada)

Canadian Parents Gifting Money to US Children: No Gift Tax Anywhere — One Form for the Kids, One Trap for the Parents

September 14, 2026

A Canadian parent can give any amount to an American child with no gift tax in either country: Canada has none, and US gift tax doesn't apply to foreign donors giving cash or non-US assets. The child reports gifts over $100,000 on Form 3520; the parent's trap is Canadian — gifting appreciated property is a deemed sale at fair market value. Here is the clean way to move family money south.

Cross-Border Tax (U.S.–Canada)

A Canadian Inherits From a US Estate: No Canadian Tax on the Inheritance, a Stepped-Up Cost Base, and the Paperwork the Estate Handles First

September 14, 2026

Canada has no inheritance tax, so a Canadian receiving from an American estate owes nothing on receipt and takes assets at fair-market-value cost. The US estate paid whatever estate tax applied before distribution, US accounts release through transfer certificates, and what the heir keeps — US property, US accounts, an IRA — decides the ongoing Canadian file. Here is the receiving end, southbound.

Cross-Border Tax (U.S.–Canada)

A Canadian Sells US Stocks: Who Taxes the Gain? Canada Does — the US Almost Never

September 14, 2026

Capital gains on US stocks and ETFs sold by a Canadian resident are taxed by Canada alone: the US does not tax a nonresident's portfolio gains, no withholding applies to sale proceeds, and no US filing results from ordinary trading. The exceptions — real-estate-heavy companies and the 183-day trap — are narrow. Here is the clean rule and its edges.

Cross-Border Tax (U.S.–Canada)

Working Remotely From the US for the Winter: When a Canadian's Laptop Creates American Tax, and When the Treaty Says No

September 14, 2026

A Canadian employee who answers email from the Florida condo is performing employment in the United States — US-source income by the basic rule. The treaty's short-stay exemption usually rescues the snowbird who works a little; the formula stops rescuing people who work a lot, and self-employment runs on different rules entirely. Here is where the lines sit.

Cross-Border Tax (U.S.–Canada)

A Child Born in the US to Canadian Parents: a Citizen at Birth, a Taxpayer for Life — What That Means and When It Starts Mattering

September 14, 2026

Birth on US soil makes the child a US citizen automatically — snowbird winters, work postings, and border-hospital deliveries have created thousands of accidental Americans in Canadian families. The citizenship brings lifelong US filing obligations that lie dormant through childhood and activate with the child's first income, first TFSA, and first job. Here is the timeline, and the choices at each stage.

Cross-Border Tax (U.S.–Canada)

Claiming Dependants Across the Border: Supporting Parents in Canada, Kids in the US, and What Each Country's Return Will Actually Give You

September 14, 2026

Supporting family on the other side of the border raises the same question in both directions: does the support earn anything on the tax return? Canada's dependant credits can extend to non-resident dependants with strict substantiation; the US's dependent rules mostly stop at its borders for credits that pay. Here is what each system allows, and the records that make claims survive.

Cross-Border Tax (U.S.–Canada)

CPP and OAS After Moving to the US: Both Are Payable, Only the US Taxes Them, and OAS Escapes the Clawback

September 14, 2026

Canadian retirement benefits travel south cleanly: CPP and OAS are paid to US residents, the treaty makes them taxable only in the US — where they slot into the Social Security rules, taxed on at most 85% — and the OAS recovery tax does not apply to US residents. Here is how the benefits work from the other side of the border.

Cross-Border Tax (U.S.–Canada)

Survivor Benefits Across the Border: What CPP and Social Security Each Pay a Widowed Spouse, Wherever They Live

September 14, 2026

A cross-border couple's survivor is usually entitled under both systems: a CPP survivor's pension from the Canadian record, Social Security survivor benefits from the American one — each payable across the border, each taxed by the survivor's residence country, and each with claiming rules that reward sequencing. Here is what the widowed spouse of a cross-border worker actually receives.

Cross-Border Tax (U.S.–Canada)

Charitable Giving Across the Border: When Canadian Donors Can Claim US Charities, When Americans Can Claim Canadian Ones, and the College Exception That Beats Both

September 14, 2026

Each country's donation relief runs on its own registry — but the treaty opens two doors: gifts to the other country's charities can be claimed against income from that country, and gifts to a college or university you or your family attended are treated like domestic donations outright. Here is the claiming matrix, and the routing that makes big cross-border gifts fully creditable.

Cross-Border Tax (U.S.–Canada)

Tuition Across the Border: the TL11A for Canadians at US Schools, the 1098-T for Americans in Canada, and Who Can Claim What

September 14, 2026

A Canadian studying in the US can still claim Canadian tuition credits — if the school certifies a TL11A and the program meets the rules. An American (or dual) student at a Canadian university can claim US education credits — if the school participates in US federal aid. Two systems, two forms, and families that plan claims on both. Here is the matrix.

Cross-Border Tax (U.S.–Canada)

The Deemed Disposition When You Leave Canada: Exactly What Is Exempt, What Is Taxed, and Which Form Reports Which

September 14, 2026

The departure-day deemed sale has a precise perimeter: registered plans, Canadian real estate, and short-term residents' property sit outside it; portfolios, private shares, and foreign property sit inside. Three forms carry the event — T1161 lists, T1243 computes, T1244 defers. Here is the property-by-property map and the filing mechanics.

Cross-Border Tax (U.S.–Canada)

Deferring the Departure Tax: How the T1244 Election Works, What Counts as Security, and When Deferral Beats Paying

September 14, 2026

Canada lets emigrants postpone the departure tax until the property actually sells — interest-free, for as long as it takes — by electing on Form T1244 and posting security above a modest threshold. For private company shares and illiquid assets the deferral is the difference between a paper tax and a cash crisis. Here is the election end to end, and the pay-versus-defer decision.

Cross-Border Tax (U.S.–Canada)

Do I Pay Departure Tax When I Leave Canada? What Triggers It, What Escapes It, and What the Bill Actually Looks Like

September 14, 2026

Canada's departure tax is a deemed sale: leave, and most of your property is treated as sold at fair market value the day you go, with the accrued gains taxed on your final return. But the biggest asset classes — your home, your RRSP, your pension — are exempt, so many movers owe far less than they fear. Here is what is in, what is out, and how the bill is computed.

Cross-Border Tax (U.S.–Canada)

Divorce Across the Border: Support Payments, Property Splits, and Retirement Accounts When the Ex-Spouses File in Different Countries

September 14, 2026

A cross-border divorce runs one settlement through two tax systems that disagree about almost everything: Canada deducts spousal support the US no longer does, the treaty referees payments that cross, property transfers roll over differently, and dividing an RRSP or a 401(k) each has its own machinery. Here is the map for separating couples with a border between them.

Cross-Border Tax (U.S.–Canada)

Do I Charge GST/HST to US Clients? Usually No — Zero-Rating for Exports, the Proof You Need, and the Traps Inside 'Usually'

September 14, 2026

Most Canadian services and goods supplied to non-resident US customers are zero-rated: you charge 0% GST/HST and still claim back the tax on your own inputs. But zero-rating is a conclusion, not a default — it depends on what you supply, to whom, and where it's used, and the exceptions bite real businesses. Here is the decision path invoice by invoice.

Cross-Border Tax (U.S.–Canada)

Do I Still File US Taxes After Moving to Canada? Yes — Here Is What the Annual Package Actually Looks Like

September 14, 2026

Moving to Canada does not end a US citizen's or green card holder's IRS filing obligation — the US taxes by citizenship, not address. What changes is the shape of the return: foreign tax credits, new information forms, and a system where you usually owe little or nothing but must file everything. Here is the annual package for an American in Canada.

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