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)

Stock Options and RSUs When You Move From Canada to the US: Sourced by Where You Worked, Not Where You Exercise

September 14, 2026

Equity compensation ignores the departure tax and follows its own rule: the benefit is divided between the countries by where the work was performed between grant and vest, whenever exercise or vesting happens. Move mid-vest and every award becomes a two-country event with withholding in both. Here is the sourcing math for options and RSUs, and the moves worth making before the date.

Cross-Border Tax (U.S.–Canada)

Do Newcomers File the T1135? Not in Year One — Here Is the Exemption, the Clock, and What Counts After That

September 14, 2026

Form T1135 — Canada's foreign property disclosure — exempts individuals for the year they first become resident. From year two, anyone whose foreign property cost exceeds C$100,000 files annually, and for arriving Americans nearly everything left behind counts: brokerage accounts, US bank accounts, rented-out real estate. Here is the newcomer rule, what is in and out, and the penalty structure that makes the form worth respecting.

Cross-Border Tax (U.S.–Canada)

Your TFSA After Moving to the US: Why the Answer Is Usually Close It Before You Go

September 14, 2026

The TFSA's magic is Canadian-only: the US taxes its income annually, contribution room freezes, non-resident contributions are penalized, and the account that was tax-free becomes a small foreign account with outsized paperwork. Here is what happens to a TFSA at the border, and why closing it pre-departure is the standard advice.

Cross-Border Tax (U.S.–Canada)

Traditional and Roth IRAs After Moving to Canada: the Treaty Election, the Canadian Contribution Trap, and How Each Is Taxed

September 14, 2026

Both IRA types survive a move to Canada, but they behave differently: the traditional IRA defers automatically like a pension, while the Roth keeps its tax-free character only if a one-time treaty election is filed — and loses it partially forever if you contribute a single dollar after becoming Canadian-resident. Here is the rulebook for each.

Cross-Border Tax (U.S.–Canada)

Transfer Pricing for Small Cross-Border Companies: the Arm's Length Rule, the T106 and 5472 Forms, and the File That Keeps Both Sides Calm

September 14, 2026

The moment your Canadian company and your US company transact with each other — services, goods, loans, a shared owner's time — both countries require arm's length pricing and annual disclosure: Canada's T106, America's 5472, and contemporaneous documentation behind the numbers. Here is transfer pricing scaled to companies with two entities and one owner.

Cross-Border Tax (U.S.–Canada)

Running a Canadian Company and a US Company: When the Two-Entity Structure Is Worth It, How Money Moves Between Them, and the Annual File That Keeps It Legal

September 14, 2026

At some point the cross-border business asks whether one corporation is still enough — and the two-company answer brings real benefits (liability walls, commercial fit, clean payroll) at the price of a permanent intercompany discipline: transfer pricing, twin information returns, and deliberate repatriation. Here is when to build the pair, how to run it, and how money actually comes home.

Cross-Border Tax (U.S.–Canada)

A US Work Assignment Under 183 Days: When the Treaty Keeps a Canadian Employee Out of the US Tax System Entirely

September 14, 2026

Article XV of the treaty exempts a Canadian resident's pay for US workdays if the pay stays under US$10,000 — or if US presence stays under 183 days in any twelve-month period and no US employer or US permanent establishment bears the cost. Get the three conditions right and a secondment produces no US return at all; miss one and payroll splits across the border. Here is the test and its traps.

Cross-Border Tax (U.S.–Canada)

The Unlimited Liability Company: the Canadian Hybrid US Planners Love, the Treaty Trap Inside It, and Where a ULC Still Earns Its Keep

September 14, 2026

The ULC — a Canadian corporation the US can treat as a flow-through — was the darling of cross-border structuring until the treaty's anti-hybrid rule stripped withholding relief from its classic dividend flows. It survives in narrower roles: US buyers acquiring Canadian targets, check-the-box planning, and structures engineered around the trap. Here is what a ULC is, where Article IV(7) bites, and the workarounds that keep the useful cases alive.

Cross-Border Tax (U.S.–Canada)

A US Business Selling Into Canada: When GST/HST Registration Hits You, the Simplified vs Normal Regimes, and the Import Mechanics

September 14, 2026

Canada's sales tax reaches non-resident vendors deliberately: digital products and services to Canadian consumers, marketplace and warehouse sales, and conventional selling with Canadian presence each trigger registration under distinct regimes. Add import GST at the border and provincial taxes on top. Here is the US seller's Canadian map.

Cross-Border Tax (U.S.–Canada)

US Casino Winnings as a Canadian: the 30% Taken at the Cage, and the Treaty Refund Most Players Never Claim

September 14, 2026

Win big in Vegas and the casino withholds 30% before you leave the floor — but the Canada-US treaty lets Canadians deduct their US gambling losses against those winnings and reclaim tax on the difference, via an ITIN and a 1040-NR. Here is which games withhold, how the refund math works, and the records that make it claimable.

Cross-Border Tax (U.S.–Canada)

US Citizenship Through a Parent: Does Your Canada-Born Child Already Have It — and What Follows If They Do

September 14, 2026

A child born in Canada to a US-citizen parent may be a US citizen automatically — if the American parent lived in the US long enough before the birth. The transmission rules decide by physical-presence arithmetic, and the answer determines whether the child has lifelong US filing obligations or a choice their parents can make. Here is the test, and what each answer means.

Cross-Border Tax (U.S.–Canada)

A US Company Hiring Canadian Contractors: the W-8BEN Instead of the 1099, and Why Remote Work in Canada Means No US Withholding

September 14, 2026

When an American company pays a Canadian contractor who works from Canada, the compensation is foreign-source income of a foreign person — no US withholding, no 1099, just a W-8BEN (or W-8BEN-E) in the vendor file proving why. The exceptions track where the work happens and what the payment really is. Here is the US payer's map, and the Canadian contractor's own side of it.

Cross-Border Tax (U.S.–Canada)

US Dividend Withholding for Canadian Investors: Why 15% Comes Off the Top, Where It Doesn't, and How the Credit Comes Back

September 14, 2026

Every US dividend a Canadian earns arrives 15% lighter — the treaty rate collected at source — and Canada then taxes the full dividend with a credit for the withholding. But the rate, the credit, and even whether withholding applies at all depend on the account it sits in: taxable, RRSP, or TFSA give three different answers. Here is the map, account by account.

Cross-Border Tax (U.S.–Canada)

US Parents Gifting to Canadian Children: the Gift Tax Belongs to the Giver — Annual Exclusions, Form 709, and the Canadian Side's Silence

September 14, 2026

When an American parent gives to a Canadian child, the US gift tax rules follow the parent: annual exclusions per child, the lifetime exemption above them, Form 709 to track it — while Canada asks the recipient nothing at all. Here is how the giving side works, what the Canadian child reports (almost nothing), and the property choices that keep it clean.

Cross-Border Tax (U.S.–Canada)

A US Person Inherits From Canada: No US Tax on the Inheritance — but Form 3520 Reporting, Basis Questions, and What You Now Own

September 14, 2026

An American inheriting from a Canadian parent owes no US income or estate tax on the inheritance itself — but bequests over $100,000 must be reported on Form 3520 with brutal penalties for silence, the inherited assets arrive with basis and account questions, and what was inherited (a house, a RRIF, a trust interest) decides the ongoing file. Here is the receiving end, in order.

Cross-Border Tax (U.S.–Canada)

Keeping Your US Remote Job While Living in Canada: Whose Payroll, Whose Taxes, and What Your Employer Needs to Know

September 14, 2026

Working a US job remotely from Canada moves the employment to Canada in the eyes of both tax systems: Canada taxes the wages first, Canadian payroll obligations attach to your employer, and the W-2 machine you left running becomes a refund-and-reconcile exercise. Here is how the taxes actually flow, and the employer conversation that makes it work.

Cross-Border Tax (U.S.–Canada)

Why Every US Bank and Broker Asks Canadians for a W-8BEN — and What Happens to Your Withholding If You Skip It

September 14, 2026

The W-8BEN is the form that tells a US payer two things: you are not American, and the treaty entitles you to reduced withholding. Signed, it drops dividend withholding from 30% to 15% and exempts most interest entirely; missing or expired, the default rates and even backup withholding apply. Here is what the form does, line by line, and its life cycle.

Cross-Border Tax (U.S.–Canada)

What Happens If I Spend More Than 183 Days in the US? The Form 8840 Door Closes and the Treaty Door Opens

September 14, 2026

Cross 183 actual days in a calendar year and the snowbird's usual fix — the closer connection exception — is no longer available: you are a US tax resident by formula, and the only route back is the treaty tie-breaker, claimed on a 1040-NR with a disclosure form, with real filing consequences either way. Here is what actually changes at day 184, and the triage if it already happened.

Cross-Border Tax (U.S.–Canada)

When Do I Become a Canadian Tax Resident After Moving? The Date, the Ties, and Why It Is Usually Arrival Day

September 14, 2026

Canadian tax residency does not start with a visa or a PR card — it starts when significant residential ties to Canada exist, which for most movers is the day they arrive to live. Here is how the CRA determines the date, what the 183-day deemed rule adds, how the treaty breaks ties for people straddling both countries, and why the exact date is worth real money.

Cross-Border Tax (U.S.–Canada)

When Do I Stop Being a Canadian Tax Resident? The Departure Date, the Ties That Hold You, and Why the CRA Looks Back

September 14, 2026

Canadian tax residency ends when significant residential ties end — usually the day you leave with your home, spouse, and dependants moved or moving. But ties left behind (a house kept available, a spouse staying, provincial health cards that linger) can hold residency open, and the departure date you claim drives the departure tax, the final return, and everything after. Here is how the date is actually determined.

Cross-Border Tax (U.S.–Canada)

Do Bare Trusts Still Have To File a T3? The Rules, the Exemptions, and Where They Stand Now

September 13, 2026

Canada's expanded trust reporting caught millions of bare trust arrangements — a parent on a child's mortgage, a joint account for convenience, a nominee on title. The CRA then exempted bare trusts for 2023 and again for 2024 while the rules were reworked. Here is what a bare trust is, why the filing rule reached it, what the exemptions cover, and what a cross-border family should do while the final rules settle.

Cross-Border Tax (U.S.–Canada)

Both Countries Auditing the Same Income: What Happens, Who Goes First, and How the Treaty Keeps It From Being Taxed Twice

September 13, 2026

When the CRA and the IRS both examine the same cross-border income, the risk is an adjustment on one side with no matching adjustment on the other. Here is how the two examinations interact, the foreign tax credit redetermination rules that follow, the treaty's mutual agreement procedure, and the sequencing that protects the taxpayer.

Cross-Border Tax (U.S.–Canada)

Can I Ask the CRA to Cancel Penalties and Interest? Yes, Under Taxpayer Relief, Within Ten Years, for Reasons the CRA Recognizes

September 13, 2026

The CRA's taxpayer relief provisions let it cancel or waive penalties and interest for circumstances beyond the taxpayer's control, CRA errors or delays, financial hardship, and other circumstances. The request is Form RC4288, within ten calendar years of the tax year. Here is what the CRA accepts, what it does not, and how a cross-border taxpayer frames the request.

Cross-Border Tax (U.S.–Canada)

A Canadian Trust With a US Beneficiary: Form 3520, UNI, and the Throwback Tax That Punishes Waiting

September 13, 2026

When a Canadian trust distributes to a US-person beneficiary, the US wants a Form 3520 — and if the trust accumulated income in earlier years, the distribution can carry the throwback tax: prior years' rates, an interest charge compounding from those years, and no capital gains treatment. Here is how UNI builds, how the default and actual methods differ, and how trustees keep distributions clean.

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