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.
September 14, 2026
Canada offers arriving Americans a menu of registered accounts, and US tax law disqualifies most of the menu's advantages. The RRSP works cleanly under the treaty; the TFSA and FHSA are tax-free only to Canada; and the wrong investments inside any of them add PFIC filings. Here is the account-by-account verdict for a US citizen living in Canada.
Read more →September 14, 2026
The classic Canadian owner-manager arithmetic — salary or dividends, roughly integrated either way — breaks when the owner files a 1040: GILTI taxes the corporation's retained profit currently, dividends lose their US character advantages, and salary becomes the mismatch-free channel. Here is the compensation math with the American overlay, and the mix that usually wins now.
Read more →September 14, 2026
US acquirers change the deal's tax texture: they push for assets or step-up structures while your lifetime capital gains exemption wants a share sale; earnouts, escrows, and rollover equity each carry two-country treatment; and the closing mechanics add withholding questions. Here is the seller-side map for the exit that crosses the border.
Read more →September 14, 2026
Sell before you leave and the principal residence exemption usually makes the gain tax-free with no process. Sell after, and you are a non-resident vendor: the exemption still covers your resident years, but section 116 clearance applies, the buyer withholds 25% until the CRA certificate arrives, and the US may tax its share. Here is the before/after comparison and the clearance process.
Read more →September 14, 2026
The US home you left behind can usually be sold with little or no tax in either country — if it sells within the right window. The section 121 exclusion runs on a two-of-five-year clock from when you moved out, and Canada only taxes gain accruing after your arrival, measured from the arrival-date value. Here is the timing math and the traps for renters-out and procrastinators.
Read more →September 14, 2026
When a Canadian sells US real estate, the buyer must withhold 15% of the gross price under FIRPTA — a prepayment, not the tax. A withholding certificate can shrink it to the real liability, the 1040-NR settles the actual gain at capital gains rates, and Canada taxes the same sale with a credit. Here is the closing-table mechanics and the refund math.
Read more →September 14, 2026
Borrowing from your own corporation is routine planning domestically and a two-rulebook problem across the border: Canada's subsection 15(2) includes unrepaid shareholder loans in income with a one-year fuse, the US imputes interest and can find deemed dividends, and cross-border configurations add withholding and PUC angles. Here is the map for owners on either side.
Read more →September 14, 2026
For Canadian professionals, incorporation's case is deferral — earn at 12%, invest the difference, pay yourself later. For a US citizen, GILTI deletes the deferral and Form 5471 adds rent, so the classic advice inverts. Sometimes the corporation still wins: liability, partners, a genuine business. Here is the decision framework run honestly, factor by factor.
Read more →September 14, 2026
Moving to Canada does not forfeit Social Security — credits stay earned, benefits are payable to Canada, the totalization agreement fills qualification gaps, and the treaty hands taxation of the benefit exclusively to Canada, which exempts 15% of it. Medicare is the opposite story: it does not travel. Here is how the retirement-benefits picture reassembles north of the border.
Read more →September 14, 2026
The federal side of snowbird life is settled by the 8840 and the treaty — but states run their own residency and source rules, and neither instrument binds them. Florida, Arizona, and Texas ask nothing; California and New York can, if a snowbird's pattern meets their tests or their income touches their soil. Here is where state exposure actually comes from and how the classic destinations compare.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
Read more →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.
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