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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)

Moving a Business From Canada to Florida: The Corporate Departure Tax, Continuance, the New U.S. Company, and the Owner's Own Emigration

October 1, 2026

A Canadian owner moving to Florida often wants the business to come too — and a Canadian corporation can't simply relocate: continuing it out of Canada triggers a corporate departure tax on its unrealized gains and an extra tax on its surplus, while leaving it in Canada with a non-resident owner creates its own issues. Here is each route — continuance, selling the assets to a new U.S. company, keeping the Canadian corporation, and winding it up — with the owner's personal departure tax alongside.

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Cross-Border Tax (U.S.–Canada)

Departure Tax Paid to Canada, Gain Taxed Again in the US? The Treaty Election That Resets Your US Basis

September 18, 2026

Canada taxes your accrued gains when you leave; the US, when you arrive, keeps your historical cost basis — so a later US sale taxes the same pre-departure gain a second time with no Canadian tax to credit that year. The treaty's departure election fixes it: you may elect to treat the property as sold and reacquired for US purposes at the same value Canada used, aligning the two countries' basis. Here is the election, which property it covers, how it's made, and what happens without it.

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Cross-Border Tax (U.S.–Canada)

Paid Departure Tax, Then the Asset Fell: The Loss Carryback Election That Refunds Part of It

September 18, 2026

Departure tax is computed on the fair market value the day you leave. If the property later sells for less — the private company that stumbled, the portfolio that dropped — you paid Canadian tax on a gain that never materialized. The Income Tax Act allows an emigrant who sells deemed-disposed property at a loss while non-resident to elect to reduce the departure-year deemed proceeds, generating a refund. Here is the election, its limits, and the sequence.

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Cross-Border Tax (U.S.–Canada)

Returning to Canada With Property You Still Own: The Election That Unwinds Your Old Departure Tax

September 18, 2026

Departure tax treats emigration as a sale — you paid Canadian tax on gains you never realized. If you come back still owning that property, the Income Tax Act lets you elect to undo the deemed disposition: the property is treated as never having been sold on departure, the tax you paid is refunded, and the original cost base is restored. Here is how the unwind works, which property qualifies, the interaction with any security you posted, and why the old departure file is the key.

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Cross-Border Tax (U.S.–Canada)

Sell the Canadian Business Before You Move or After? The Capital Gains Exemption, the CFC Rules, and the Answer That Depends on the Buyer

September 18, 2026

A business owner moving to the US with a sale in view faces a timing decision worth six or seven figures: sell as a Canadian resident and use the lifetime capital gains exemption, or sell after the move and face departure tax on the shares, US tax on the gain, and a year or more inside the CFC regime. The clean answer is usually 'before' — unless the buyer, the deal structure, or the exemption's qualification tests say otherwise. Here is the analysis.

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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.

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Cross-Border Tax (U.S.–Canada)

Deferring the Departure Tax: How the T1244 Election Works, What Counts as Security, and When Deferral Beats Paying

September 14, 2026

Canada lets emigrants postpone the departure tax until the property actually sells — interest-free, for as long as it takes — by electing on Form T1244 and posting security above a modest threshold. For private company shares and illiquid assets the deferral is the difference between a paper tax and a cash crisis. Here is the election end to end, and the pay-versus-defer decision.

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Cross-Border Tax (U.S.–Canada)

Do I Pay Departure Tax When I Leave Canada? What Triggers It, What Escapes It, and What the Bill Actually Looks Like

September 14, 2026

Canada's departure tax is a deemed sale: leave, and most of your property is treated as sold at fair market value the day you go, with the accrued gains taxed on your final return. But the biggest asset classes — your home, your RRSP, your pension — are exempt, so many movers owe far less than they fear. Here is what is in, what is out, and how the bill is computed.

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Cross-Border Tax (U.S.–Canada)

What Happens to My RRSP When I Move to the US? Keep It Growing, or Collapse It at 25% — the Real Comparison

September 14, 2026

The RRSP survives a move to the US better than any other Canadian account: no departure tax, continued deferral in both countries, and a choice worth real money — leave it growing, convert to a RRIF for 15% treaty withholding on periodic payments, or collapse it at 25%. Here is how each path is taxed and how the US measures its share.

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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.

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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.

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Cross-Border Tax (U.S.–Canada)

A US Person as Trustee of a Canadian Trust: How One Appointment Can Move the Trust's Residence — or Make It American

September 13, 2026

Naming the responsible sibling in Seattle as trustee of the family trust feels natural and can be a structural mistake: Canada locates a trust where its central management and control happens, and the US applies its own court and control tests. One US trustee can trigger a Canadian departure tax for the trust, US filings, or both. Here is how the two residence tests work and how to appoint safely.

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