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Guides

Straight answers, written by the people who’d file it.

1,407 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.

CROSS-BORDER A Canadian Corporation With a U.S. Shareholder
  • What applies to you
  • What it costs if you wait
  • What to do next
1,407 guides
Cross-Border Tax (U.S.–Canada)

TFSA and Roth IRA: Look-Alike Accounts That Each Country Refuses to Recognize From the Other

September 18, 2026

The TFSA and the Roth IRA are the same idea — after-tax contributions, tax-free growth, tax-free withdrawals — implemented by two countries that don't honor each other's version. A Canadian's TFSA is a taxable account to the IRS; an American's Roth IRA is protected in Canada only by a treaty election most people never file. Here is how each account is treated by the other country, the elections and traps, and what a mover should do with each.

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Cross-Border Tax (U.S.–Canada)

The RDSP After a Move to the US: Grants Stop, the IRS Sees a Trust, and Whether to Keep It Open

September 18, 2026

The Registered Disability Savings Plan is Canada's most generous savings vehicle — government grants and bonds that can exceed the holder's own contributions — and it depends on Canadian residency in ways the RRSP and TFSA do not: grants and bonds stop when the beneficiary becomes a non-resident, contributions are barred, and the US sees an account it has no treaty provision for. Here is what happens to an RDSP when the family moves, and how to decide whether it stays open.

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Cross-Border Tax (U.S.–Canada)

Wash Sales and Superficial Losses: Two Loss-Denial Rules With Different Windows, and the Trade That Trips Both

September 18, 2026

Both countries deny a capital loss when you sell and buy back too soon — the US wash sale rule and Canada's superficial loss rule — but the rules differ in scope (securities versus identical property), in who counts (a spouse and controlled corporation in the US; an expanded affiliated-person list including your own RRSP and TFSA in Canada), in what happens to the denied loss, and in whether crypto is covered. A cross-border investor harvesting losses runs both tests on every trade. Here is the side-by-side.

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Cross-Border Tax (U.S.–Canada)

What TFSA Reporting on a US Return Actually Involves, and Why Quotes for It Vary So Much

September 18, 2026

A US citizen with a tax-free savings account gets wildly different quotes for reporting it — because the work ranges from one line on Schedule B to a stack of PFIC forms, a foreign-trust position, and two information returns, depending on what the account holds and how the preparer treats it. Here is the actual work, item by item, why the range is real, and how to shrink it to the small version.

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Cross-Border Tax (U.S.–Canada)

Registered Accounts Inside a Streamlined Submission: How the RRSP, TFSA, and RESP Each Land on the Three Catch-Up Returns

September 17, 2026

A Canadian's streamlined submission is mostly about registered accounts, and each one is treated differently: the RRSP defers under the treaty with no form now required, the TFSA is a taxable account with a possible trust-reporting question, and the RESP is a taxable account the IRS may see as a trust — with grants and growth taxed to the subscriber. Here is how each account appears on the returns, the FBARs, and the certification.

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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.

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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.

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Cross-Border Tax (U.S.–Canada)

Estate Planning With Mixed-Citizenship Children: Which Assets to Leave to the American Kid, Which to the Canadian, and Why Equal Isn't Identical

September 14, 2026

When one child files a 1040 and the other doesn't, identical bequests aren't equal: Canadian mutual funds, trust interests, and TFSA-style assets punish the American heir, while US-situs assets suit them fine. Asset-matched wills leave each child what their tax system treats kindly and equalize by value. Here is the matching logic and the drafting that implements it.

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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.

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Cross-Border Tax (U.S.–Canada)

Form 3520 Penalty Abatement: The IRS's October 2024 Policy Change and What It Means for a Late Foreign Gift or TFSA Report

September 13, 2026

The IRS used to assess Form 3520 penalties automatically on late filings, up to 25% of a foreign gift or 35% of a foreign trust transaction, and taxpayers fought them afterward. In October 2024 the IRS announced it would review reasonable-cause statements before assessing the gift and bequest penalty. Here is what changed, what did not, and how to file a late Form 3520 now.

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Cross-Border Tax (U.S.–Canada)

Streamlined Filing: The Real Cost for a Canadian, and What Drives It

September 13, 2026

The cost of a streamlined submission is driven by the number of returns and the forms each year requires, not by the tax. Three returns with a TFSA, a corporation, and Canadian mutual funds cost several times three plain returns. Here is what drives the fee, what the tax and interest look like, and how the 5% domestic penalty compares. Fairlight's pricing is published; this explains the ranges.

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Cross-Border Tax (U.S.–Canada)

How Does Streamlined Filing Work for Retirees With Canadian Pensions? CPP, OAS, an RPP, and a RRIF, Each on Its Own Line

September 13, 2026

A retired US person in Canada catching up through streamlined reports four kinds of Canadian retirement income differently: CPP and OAS (taxable only in Canada under the treaty), an employer pension (taxable in both with a credit), RRIF withdrawals (pension income with basis recovery), and any TFSA the retiree opened. Here is each, with the treaty positions and the forms.

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Cross-Border Tax (U.S.–Canada)

What Happens to Your RRSP, TFSA, and RESP in a Streamlined Filing: Deferral Restored, Earnings Taxed, Trust Forms Filed

September 7, 2026

The three Canadian registered accounts are treated differently in a streamlined submission. The RRSP's treaty deferral is restored retroactively under Rev. Proc. 2014-55 and the account goes on the FBAR. The TFSA's earnings are added to income for the three years and Forms 3520 and 3520-A are filed. The RESP is the same as the TFSA with the grant taxed too. Here is each account, form by form.

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