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)

Streamlined Fixes the Federal Years Only: The State Returns the Program Never Touched and How to Clean Them Up

September 17, 2026

A streamlined submission repairs three years of federal returns and six of FBARs — and says nothing about the state. If any covered year included US-state residency, or state-source income, the state return for that year is still missing or wrong, and the state has its own penalties, its own statute, and in most cases its own voluntary disclosure program. Here is the state layer streamlined leaves behind.

Cross-Border Tax (U.S.–Canada)

Streamlined or the IRS Voluntary Disclosure Practice? Where Willfulness Moves You From One Door to the Other

September 17, 2026

Two IRS programs fix undisclosed foreign accounts, and the line between them is willfulness: streamlined for negligence, inadvertence, and honest misunderstanding; the Voluntary Disclosure Practice for conduct that was — or might be argued to be — deliberate. Choosing wrong in either direction is expensive. Here is how the two compare, the facts that move a file across the line, and the process for the harder door.

Cross-Border Tax (U.S.–Canada)

Unfiled US Returns With Only a Salary Behind Them: Whether Streamlined Is Still the Route When No Accounts Were Hidden

September 17, 2026

Not every unfiled American in Canada has a foreign-account problem. Some simply never filed, with employment income taxed in Canada and ordinary bank accounts below every threshold. Streamlined was built around offshore assets — so does the salaried non-filer use it, the delinquent-return route, or simply start filing? Here is the sort, and why the answer depends on which forms were actually owed.

Cross-Border Tax (U.S.–Canada)

The Ways a Streamlined Submission Fails: Missing Signatures, Thin Certifications, Wrong Track, and the Fixes Before You Mail It

September 17, 2026

The IRS does not send acceptance or rejection letters for streamlined submissions — it processes them, or it doesn't, or it treats them as ordinary filings without the program's protection. The failures are procedural far more often than substantive: a form unmarked, a certification unsigned, FBARs filed the wrong way, a track chosen wrong. Here is the failure list and the pre-mailing checklist that prevents it.

Cross-Border Tax (U.S.–Canada)

An American Buying Property in Canada: the Foreign Buyer Prohibition, the 25% Provincial Taxes, and the Purchases That Are Still Possible

September 15, 2026

US citizens face a wall of made-in-Canada rules before any tax planning starts: a federal prohibition on non-Canadian purchases of residential property (in force until 2027), Ontario's 25% Non-Resident Speculation Tax, and BC's parallel regime — plus the Underused Housing Tax, now eliminated for 2025 and later years but still a legacy issue for anyone who held in 2022–2024. Here is what's actually barred, what's exempt, and how the permitted purchases get structured.

Cross-Border Tax (U.S.–Canada)

Can the CRA Collect for the IRS — or the IRS for the CRA? Article XXVI A, the Citizenship Carve-Out, and What Cross-Border Debtors Should Actually Expect

September 15, 2026

The Canada-US treaty contains something rare: a mutual collection assistance article. Each country can ask the other to collect its finally-determined tax debts with the full domestic toolkit — subject to a carve-out protecting each country's own citizens for debts that arose while they were citizens. Here is how the machinery works and who it actually reaches.

Cross-Border Tax (U.S.–Canada)

A Canadian Buying US Property: the Tax Checklist That Should Run Before Closing — Title, Future Taxes, and the Paperwork That Isn't Needed Yet

September 15, 2026

Buying US real estate as a Canadian triggers no US tax at purchase — the tax story is entirely about setup: how title is taken, what the property will do (personal use, rental, both), and which future regimes (rental withholding, FIRPTA, estate exposure) the purchase quietly enrolls you in. Here is the pre-closing checklist, item by item.

Cross-Border Tax (U.S.–Canada)

Civil Penalties vs Criminal Tax Evasion Across the Border: Where the Line Actually Sits, the Warning Signs, and When the Next Call Is a Lawyer

September 15, 2026

Almost every cross-border tax problem is a civil matter — money, penalties, interest, resolvable through the repair procedures. A small set cross into criminal territory, and the line is willfulness: deliberate violation of known duties. Knowing where the line sits, and the moments that demand privilege, protects people on both sides of it.

Cross-Border Tax (U.S.–Canada)

Double-Taxed by Canada and the US Anyway? The Mutual Agreement Procedure: When to Invoke It, How It Runs, and What It Actually Fixes

September 15, 2026

When both countries tax the same income and the credit machinery can't fix it — a transfer pricing adjustment, a residency dispute, mismatched sourcing — the treaty's mutual agreement procedure puts the two competent authorities in a room to resolve it, with binding arbitration as the backstop. Here is the relief of last resort, and how to preserve access to it before you need it.

Cross-Border Tax (U.S.–Canada)

Converting a Home to a Rental Across the Border: Canada's Deemed Disposition and Elections, America's Basis Rules, and the Conversions That Follow a Move

September 15, 2026

Turning a home into a rental is a tax event before it's a landlording one: Canada deems a disposition at fair market value with elections that can defer it and extend the principal residence years; the US resets the depreciation basis and starts the non-qualified-use and recapture clocks. Movers convert across two systems at once — and the election deadlines don't wait. Here is the conversion playbook.

Cross-Border Tax (U.S.–Canada)

A CRA Review Letter vs an Audit: Which One You Got, What Each Can Do, and How Cross-Border Filers Should Answer

September 15, 2026

Most CRA letters are not audits — they are reviews: automated or desk checks asking you to support a claim or explain a mismatch, resolved by sending documents. An audit is a different animal with different powers. Cross-border filers draw more of both. Here is how to tell them apart and handle each.

Cross-Border Tax (U.S.–Canada)

CRA Taxpayer Relief: When Canada Cancels Interest and Penalties, the Ten-Year Deadline, and Building an RC4288 That Gets Granted

September 15, 2026

The CRA can cancel or waive penalties and interest — not tax — where circumstances beyond your control, CRA delays, or genuine inability to pay caused or compounded the charges. Requests go in on Form RC4288 against a hard ten-year limitation, and outcomes track documentation quality. Here is the program, the grounds, and the request that works.

Cross-Border Tax (U.S.–Canada)

The CRA's Voluntary Disclosures Program for Cross-Border Filers: Two Tracks, Five Conditions, and Coming Forward Before They Find You

September 15, 2026

Canada's VDP lets taxpayers correct past non-compliance — unreported foreign income, missed T1135s, unfiled returns — with penalty relief and partial interest relief, if the disclosure is voluntary, complete, and meets the program's conditions. Cross-border files add a second country's fix to coordinate. Here is how the program works and how to build a disclosure that qualifies.

Cross-Border Tax (U.S.–Canada)

Short-Term Rentals Across the Border: When Airbnb Income Stops Being Rental Income, the GST/HST Registration Trap, and the Lodging Tax Stack

September 15, 2026

Short-term rental income breaks the assumptions the long-term playbooks run on: in Canada it's a taxable supply that forces GST/HST registration past the threshold and can convert the property's character; in the US it can shift from Schedule E to self-employment, and the platform's tax collection covers less than hosts assume. Here is the STR overlay for cross-border owners.

Cross-Border Tax (U.S.–Canada)

Cross-Border Mortgages: Who Will Lend, What the Interest Deducts Against, and the Structures That Waste or Save the Write-Off

September 15, 2026

Financing property across the border is two problems: getting the loan (thin credit files, cross-border lenders, the currency question) and taxing the interest (the US deducts home mortgage interest; Canada doesn't — but both deduct interest against rental income, and the tracing rules decide everything). Here is the lending landscape and the deductibility map.

Cross-Border Tax (U.S.–Canada)

Cross-Border REIT Investing: US REITs in Canadian Hands, Canadian REITs in American Hands, and the Account-Location Rules That Decide the Yield

September 15, 2026

Real estate exposure through REITs swaps property-level tax problems for securities-level ones: US REIT distributions carry their own withholding quirks (return of capital, capital gain distributions, and rates that differ from ordinary dividends), Canadian REITs are presumptively PFICs for US persons, and the RRSP/TFSA/taxable location decision moves after-tax yield by whole percentage points. Here is the map.

Cross-Border Tax (U.S.–Canada)

Does a 1031 Exchange Work for Canadian Property? The Foreign-for-Foreign Rule, Canada's Missing Rollover, and What Cross-Border Investors Use Instead

September 15, 2026

US investors defer real estate gains through 1031 exchanges — but US property is not like-kind to foreign property, so you can't exchange Phoenix for Toronto. Foreign-for-foreign works on the US side; Canada, meanwhile, has no 1031 at all and taxes the disposition regardless. Here is what survives the border, what doesn't, and the substitute strategies.

Cross-Border Tax (U.S.–Canada)

The Family Cottage With Cross-Border Heirs: Deemed Dispositions, American Children, and the Succession Structures That Actually Keep the Place

September 15, 2026

Passing the cottage down is Canada's classic estate problem — the deemed disposition at death taxes decades of appreciation with no cash to pay it — and American heirs add a second layer: rental characterization, 3520 reporting, and eventually their own US-situs planning in reverse. Here is the succession toolkit with the cross-border overlay.

Cross-Border Tax (U.S.–Canada)

A FATCA Letter From Your Canadian Bank: What It Means, What They Already Report, and the Right Order of Next Moves

September 15, 2026

The letter asking about your US status — a W-9 request, a 'US indicia' questionnaire — means your bank's systems flagged you, and under the Canada-US information-sharing agreement your account data may flow to the IRS through the CRA. The letter itself is routine; the compliance status it illuminates is the real question. Here is what to do, in order.

Cross-Border Tax (U.S.–Canada)

Florida Property Tax for Canadian Owners: No Homestead, No Cap, and the Assessment Math Snowbirds Should Run Before Buying

September 15, 2026

Florida's celebrated property tax breaks — the homestead exemption and the Save Our Homes cap — belong exclusively to permanent Florida residents, which excludes every snowbird by definition. Canadian owners pay full millage on full assessed value with a softer 10% cap, and the gap versus their homesteaded neighbors widens every year. Here is the system, the math, and what actually helps.

Cross-Border Tax (U.S.–Canada)

Holding US Real Estate Through a Canadian Corporation: the Structure That Solved a 1990s Problem and Creates Five Modern Ones

September 15, 2026

The Canadian holdco owning the Florida house was once standard estate-tax planning; today it manufactures shareholder benefits on every personal-use week, corporate FIRPTA and branch tax on exit, stacked filings in both countries, and worse rates on rental income — while the treaty credits solved the original problem for most estates. Here is why the structure persists, what it actually costs, and how existing ones unwind.

Cross-Border Tax (U.S.–Canada)

How Americans Should Hold Canadian Real Estate: Personal Title Wins, the LLC Fails Twice, and the Narrow Cases for Anything Else

September 15, 2026

The American buying Canadian property inherits the mirror of every Canadian-buying-US structuring question — and the answer mirrors too: personal title beats the vehicles. The US LLC that protects at home misclassifies in Canada; trusts import two countries' reporting; corporations stack taxes. Here is the holding-structure decision from the American side, case by case.

Cross-Border Tax (U.S.–Canada)

How Far Back Can the CRA and IRS Go? Reassessment Periods, the Six-Year Doors, and the Years That Never Close

September 15, 2026

Each system promises finality on a clock: Canada's normal reassessment period runs three years from assessment, the IRS's statute runs three from filing — and each has doors that extend to six, and conditions that suspend the clock entirely. Unfiled returns and unreported foreign assets are the classic forever-cases. Here is the limitation map for cross-border filers.

Cross-Border Tax (U.S.–Canada)

An IRS Audit While Living in Canada: What Expat Audits Actually Look Like and How to Run One From Abroad

September 15, 2026

For a US citizen in Canada, an IRS audit almost never means a visit — it means correspondence: a letter proposing questions or changes, deadlines that assume US mail speeds, and issues that cluster around the expat forms. Here is what triggers expat audits, how the process runs remotely, and the file management that decides outcomes.

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