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)

The IRS CP2000 Notice With Canadian Income in the Mix: Why the Matching Computer Is Wrong More Often for Expats, and How to Answer It

September 15, 2026

A CP2000 proposes extra tax because the IRS's information returns don't match your 1040 — and for cross-border filers the mismatch is often the computer missing your foreign tax credit, double-counting a slip, or reading gross where you correctly reported net. It is a proposal, not a bill. Here is how to read one, and the response that closes it.

Cross-Border Tax (U.S.–Canada)

IRS Penalty Relief: First-Time Abatement's Free Pass, the Reasonable Cause Standard, and How Cross-Border Filers Should Ask

September 15, 2026

The IRS waives billions in penalties annually through two doors: First Time Abate — a clean-history administrative pass for filing and payment penalties, granted almost mechanically — and reasonable cause, the facts-and-circumstances standard that covers what FTA doesn't, including the international information return penalties expats fear most. Here is how each works and how to write requests that succeed.

Cross-Border Tax (U.S.–Canada)

Land Transfer Taxes and Closing Costs: What It Actually Costs to Buy in Canada vs the US, Line by Line

September 15, 2026

Canadian buyers pay land transfer taxes that can reach 4-5% in Toronto with the foreign-buyer surtaxes on top; US buyers trade lower transfer taxes for title insurance, higher legal-adjacent fees, and property-tax proration quirks. Neither side's costs are deductible for personal homes — but every line lands somewhere: basis, expense, or nowhere. Here is the closing statement decoded, both directions.

Cross-Border Tax (U.S.–Canada)

Owing the CRA While Living in the US: Payment Arrangements, What Canadian Collections Can Reach, and the Citizen Carve-Out Running the Other Way

September 15, 2026

A CRA debt follows the emigrant south — interest compounds, Canadian-source income and accounts remain exposed, benefits and refunds offset, and the treaty lets the CRA ask the IRS to collect finally-determined debts, except generally against US citizens whose debt arose while they were US citizens. Here is the southbound debtor's map, and the arrangements that resolve it.

Cross-Border Tax (U.S.–Canada)

Owing the IRS While Living in Canada: Payment Plans, the Offer Route, and What US Collections Can Actually Reach

September 15, 2026

A US tax debt doesn't expire at the border — interest and penalties run, refunds offset, passports certify, and the treaty gives the IRS a collection arm in Canada in some cases. But the resolution menu also works from abroad: installment agreements, currently-not-collectible status, and offers in compromise. Here is the debtor's map from north of the border.

Cross-Border Tax (U.S.–Canada)

Pre-Construction Condos Across the Border: Assignment Sales, the New Housing Rebate, and Why the Flipping Rules Watch This Market

September 15, 2026

Pre-construction buying runs on its own tax rails: deposits and occupancy fees before title, GST/HST embedded in new-home prices with rebates that depend on your intentions, assignment sales taxed as business income with GST on top, and the flipping rule timing everything. Add a border — the US buyer of a Toronto pre-con, the Canadian buying Miami pre-construction — and intentions get audited. Here is the map.

Cross-Border Tax (U.S.–Canada)

Canada's Principal Residence Exemption vs America's Section 121 Exclusion: Two Home-Sale Shelters That Don't Match, and How Movers Coordinate Them

September 15, 2026

Canada exempts the designated principal residence's gain without dollar limit; the US excludes up to $250,000/$500,000 with ownership-and-use tests. For anyone who files in both systems — or moves between them — the mismatches decide real tax: unlimited vs capped, designation vs mechanical tests, and the timing windows that reward planned sales. Here is the side-by-side and the coordination playbook.

Cross-Border Tax (U.S.–Canada)

Property Flipping Rules in Canada and the US: the 365-Day Deemed Business Income Rule, the Dealer Doctrine, and Where Cross-Border Flippers Get Taxed Twice at Full Rates

September 15, 2026

Canada now deems profit on housing sold within 365 days to be fully-taxed business income — no capital treatment, no principal residence exemption — while the US reaches the same result through its dealer-versus-investor doctrine and holds short gains at ordinary rates anyway. Flip across the border and both systems' full-rate regimes meet the same profit. Here is the map, the exceptions, and the intention evidence that decides the close cases.

Cross-Border Tax (U.S.–Canada)

The Underused Housing Tax: Who Had to File for 2022–2024 — and Why It's Now Eliminated

September 15, 2026

Canada's UHT was a 1% annual tax on underused residential property aimed at foreign owners — and Budget 2025 eliminated it for 2025 and later years. But the 2022, 2023, and 2024 returns still stand, and their real teeth were always the filing rules: affected owners filed a return per property even when fully exempt, with penalties attached to the missing form. Here is the owner-by-owner sort, the exemption map, and what the elimination does and does not erase.

Cross-Border Tax (U.S.–Canada)

Unfiled Canadian Returns as a US Resident: Arbitrary Assessments, the VDP Route, and Catching Up From South of the Border

September 15, 2026

Behind on Canadian filings while living in the US — the emigrant who never filed the departure year, the non-resident landlord without 216 returns, the American with abandoned Canadian years? The CRA's toolkit includes assessments it writes for you; yours includes the VDP, late elections, and real numbers that beat arbitrary ones. Here is the northbound catch-up.

Cross-Border Tax (U.S.–Canada)

Unfiled US Returns as a Canadian Resident: How Many Years Back, Which Procedure, and What the Catch-Up Actually Costs

September 15, 2026

The American in Canada with years of unfiled 1040s faces a question with real procedural answers: streamlined's three-plus-six for the eligible, six years as the general practice for delinquent filers, and every year technically open because unfiled statutes never start. The tax usually rounds to little; the choice of route is everything. Here is the decision tree.

Cross-Border Tax (U.S.–Canada)

Passport Revocation for Tax Debt: How the IRS Certification Works, the Thresholds and Exceptions, and Getting Uncertified From Canada

September 15, 2026

Owe the IRS enough — an inflation-adjusted threshold ($66,000 for 2026) — with a lien filed or levy issued, and the IRS certifies the debt to the State Department, which can deny renewals and revoke passports. For an American in Canada whose passport is a practical necessity, this is the collection pressure that bites. Here is the machinery, the exits, and the timeline.

Cross-Border Tax (U.S.–Canada)

What Happens to My 401(k) When I Move to Canada? Leave It, Roll It, or Move It — the Three Options Priced

September 14, 2026

A 401(k) survives the move to Canada intact: the treaty defers Canadian tax on its growth, and distributions are taxed where you live when you take them. The real questions are whether to roll it to an IRA, whether an RRSP transfer ever makes sense, and how withdrawals will be taxed on both sides in retirement. Here are the three options with the tax mechanics of each.

Cross-Border Tax (U.S.–Canada)

529 Plans When the Family Moves to Canada: Still Tax-Free to the IRS, Just Another Account to the CRA

September 14, 2026

A 529 plan keeps every US advantage after a move to Canada — tax-free growth, tax-free qualified withdrawals, even for many Canadian universities. What it loses is Canadian recognition: the CRA has no category for it, and the prudent treatment taxes its growth annually on the Canadian return. Here is how families handle the gap, and when to spend, hold, or wind down.

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.

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