Working Remotely From Another Country: A Canadian Lawyer's Five-Point Checklist

The pitch is appealing. Keep your Canadian salary, log in from a co-working space in Lisbon or Mexico City, and live a different life for a few months. Many Canadian employers, post-pandemic, will say yes. The internet says it is straightforward. But working remotely from another country touches at least five legal regimes at once, and the cost of getting it wrong falls almost entirely on the employee, not the employer.

Here are the five things every Canadian should check before working remotely from another country, written from the perspective of an Ontario-based employment lawyer who advises on cross-border arrangements.

01.Your immigration status in the host country

This is the most common mistake, and the most consequential. A tourist visa or visa-free entry to most countries explicitly prohibits work, including remote work for a foreign employer. The fact that your salary lands in a Canadian bank account from a Canadian company does not change the analysis. If you are physically present in another country and performing economic activity there, most immigration regimes treat that as work.

Enforcement is uneven. Many people travel on tourist visas and work remotely without issue for short periods. But the legal risk is real, and the consequences range from visa cancellation to entry bans that can affect your ability to travel for years.

What to check, in order:

• Duration. How long do you plan to be there? Most countries tolerate short-term remote work under tourist rules in practice, even if not formally. Stays beyond 90 days, in most jurisdictions, push you toward needing a specific permit.
• Digital nomad visa. Dozens of countries now offer specific visas for remote workers. Portugal, Spain, Italy, Estonia, Costa Rica, Mexico, and others have programs with varying income thresholds and tax treatment. These are the cleanest legal path.
• Working visa. If you intend to stay long term, a tourist or nomad visa is not enough. You will likely need a full work or residency permit, which usually requires local sponsorship or significant investment.

02.Tax residency, and the 183-day rule

The single most important number in international remote work is 183. In most countries, spending 183 days or more within a 12-month period triggers tax residency. That means the host country can tax your worldwide income, not just income earned locally. You may be in two tax systems at the same time until a bilateral tax treaty's tie-breaker rules resolve which country has the primary claim.

Canada applies a different test. The Canada Revenue Agency uses a "significant residential ties" analysis (housing, spouse, dependents) rather than purely day-counting. You can be tax resident in Canada and another country at the same time, in which case the applicable bilateral tax treaty becomes critical. Canada has tax treaties with most major countries, including the United States, the United Kingdom, EU member states, Mexico, Australia, and many others.

03.Your employment contract, and which country's law governs

The contract you signed in Canada was drafted under Canadian law, probably one of the provincial Employment Standards Acts. When you move to another country, two questions arise: does your Canadian contract still govern, and do the host country's mandatory employment laws still apply?

The short answer is that a choice-of-law clause in a contract does not always override the mandatory employment standards of the place where work is performed. European Union member states are particularly aggressive on this point. Many treat their local termination, working time, and worker protection rules as overriding any contract that says otherwise. France, Germany, and Spain are well known for this. Some Latin American countries similarly apply local labour rules to anyone working on their soil, regardless of who employs them.

For Canadian employees, this can cut both ways. You may gain protections you did not have, such as stricter limits on termination notice in EU countries. You may also lose protections you thought you had, such as the common law reasonable notice doctrine that applies across most of Canada but is not recognized in many jurisdictions abroad.

The principle works both ways: Cicale v. Swiss International Air Lines

The Quebec Superior Court's decision in Cicale v. Swiss International Air Lines Ltd., 2025 QCCS 4421 (Poulin J.S.C.), released on November 28, 2025, offers a useful Canadian illustration of the same principle. It is worth examining in some detail because it shows that the choice-of-law question is only one part of the analysis, and that succeeding on the choice-of-law point does not necessarily mean succeeding on the underlying claim.

Ms. Cicale had worked her way up at Swiss International Air Lines over more than a decade, holding successive positions in New York and ultimately being appointed Country Manager for Canada in 2012, the most senior role in the airline's Canadian operations. She rented an apartment in Montreal, paid Quebec and federal Canadian taxes, held a Canadian work permit, and worked in Montreal four to five days a week. She retained some US benefits, supervised a small US-based team, and maintained certain administrative ties to the US organization.

In June 2014, Swiss discovered that Ms. Cicale had been self-approving a second monthly housing allowance of CAD $2,500 paid directly to her landlord, on top of the CAD $2,500 housing allowance already included in her salary. Over nearly two years, this amounted to approximately $55,000 in overpayments. Swiss issued a Letter of Disciplinary Action and proposed transferring her back to New York at a slightly reduced salary in a project-based role. Ms. Cicale refused the new role and treated the situation as a constructive dismissal. Swiss treated her refusal as a resignation effective July 31, 2014.

The choice-of-law holding

The Court applied article 3118 of the Civil Code of Québec, which provides that parties cannot, by contract, deprive an employee of the mandatory protections of the State where the employee habitually carries out their work. Swiss argued that Ms. Cicale's assignment to Quebec was temporary, that her usual place of work remained New York, and that New York's at-will doctrine should govern.

The Court rejected that argument. Justice Poulin held (at paras 41-58) that Ms. Cicale habitually carried out her work in Quebec from at least August 2012 onward. The factors that mattered were the physical location of the work, the work permit, the lease, and the fact that the role was indefinite rather than time-limited. The factors that did not matter were the administrative arrangements: US payroll, US benefits, retention of some US supervisory functions, and US tax filings. As the Court put it (at para 49), "Swiss assigned Ms. Cicale to perform a new function in Quebec and it is in Quebec that she habitually carried out her work."

Notably, the Court relied on an internal Swiss HR email from August 2012 confirming that the employee "must physically be in the US for half of the year" only to maintain US health insurance, and that her presence in the US would otherwise be "principally for her personal affairs" (paras 46-47). That contemporaneous documentation was used against the employer's later position. The lesson for employers is clear: internal communications about cross-border arrangements should be drafted with the same care as the employment contract itself.

But Ms. Cicale still lost on the underlying claim

What the case is most often summarized for is the choice-of-law holding. What is less often noted, and equally important, is that Ms. Cicale's constructive dismissal claim was dismissed (paras 60-130). The Court found that Swiss's transfer-back proposal was justified and suitable in the circumstances. Although there was reduced salary ($500 a month less), reduced scope (a defined project rather than the Country Manager role), and uncertainty about her position at the end of the project, the Court held that these changes were proportionate to the legitimate disciplinary concern, which was Ms. Cicale's self-approval of $55,000 in undocumented additional housing payments over two years (paras 81-99).

Justice Poulin found that Ms. Cicale's verbal understanding with her former supervisor (who did not testify) could not displace the written terms of her assignment (paras 91-95). The Court was particularly direct in its conclusion (at para 11): "Ms. Cicale's refusal to accept Swiss's reasonable offer caused her loss. She is the author of her own misfortune."

The Court also held that even if Ms. Cicale's constructive dismissal claim had been valid, her damages claim would have failed in several respects. She delayed her job search by approximately six months after leaving Swiss (taking time to travel and practice yoga, the judgment notes at para 139), which would have reduced any award under the mitigation duty in article 1479 C.C.Q. Her claim for 24 months of notice was, in the Court's view, "exaggerated" (para 139). Her inclusion of the disputed housing allowances in her claimed compensation was "problematic" (para 140).

Ms. Cicale received only $17,460.03, awarded as legal costs for a trial postponement caused by the defendant's late-filed jurisconsult certificate, not for the dismissal claim itself.

What employees and employers should take from Cicale

The case is most useful as authority for three propositions:

• Choice-of-law clauses can be displaced. A contract that says Ontario, New York, or any other law governs will not always override the mandatory protections of the place where the work is physically performed. For cross-border employers, this is the central planning point.
• Administrative ties do not decide the question. Payroll location, benefits enrolment, tax filings, and supervisory reporting can all point away from the workplace without changing the answer under article 3118. What matters is where the work is actually done.
• Winning on choice of law does not mean winning the case. Even where Quebec law applies, the employee must still establish that the employer's conduct amounted to constructive dismissal under the Farber framework. Where an employer responds proportionately to legitimate disciplinary concerns, even significant changes to the employee's role may not cross the line.

The practical lesson for Canadian employees considering a cross-border arrangement, or for international employers with Canadian remote workers, is that the planning matters more than the paperwork. A New York or Delaware choice-of-law clause may not insulate an employer from Canadian law if the work is performed in Canada. Conversely, a Canadian employee who relocates abroad should expect that the host jurisdiction's mandatory rules may apply to whatever work is performed there, regardless of what the Canadian contract says.

What to look at in your own contract:

• The choice-of-law clause (which province or country's law governs)
• The termination clause (whether it remains valid and enforceable if work is performed abroad)
• Working time, overtime, and rest period provisions
• Whether the contract requires you to perform duties from a specific location

04.Social security: CPP, EI, and the host country's system

Canada Pension Plan and Employment Insurance contributions are tied to where you work, not where your employer is. If you work in another country, that country's social security system may claim contributions from you, your employer, or both. Without coordination, you could end up paying into two systems and benefiting fully from neither.

The mechanism that prevents this is called a totalization agreement. According to the Canada Revenue Agency, Canada has international social security agreements with more than 50 countries, including the United States, the United Kingdom, France, Germany, Italy, the Netherlands, Australia, Japan, the Philippines, and many others. These agreements allow workers to remain covered under their home country's system for a defined period (often up to five years) by obtaining a Certificate of Coverage from the CRA.

For Canada to United States moves, the relevant Canadian form is the CPT56. Each agreement has its own form number, so the right one depends on the destination country. Without this certificate, the host country may legitimately demand contributions to its own system from day one.

05.Your employer's permission, and what it actually covers

Many Canadian employers now allow remote work from another country, sometimes for weeks or a few months at a time. But "yes, you can work from Spain for two months" is not a complete answer. The legal exposure runs in both directions. Your employer faces its own risks that you should understand, because if the employer becomes uncomfortable later, the arrangement can be revoked or used as grounds for dismissal.

Specifically, ask your employer:

• Is the permission in writing? A verbal yes is not enough. Get an email confirming the dates, the country, and the conditions. This protects you if the manager who agreed leaves or changes their mind.
• What's the duration cap? Many companies have an internal limit (often 30, 60, or 90 days per year) tied to their own tax and permanent establishment exposure.
• Has the company addressed permanent establishment risk? If you have authority to sign contracts, manage a team, or generate revenue while abroad, your activities can create a "permanent establishment" of your employer in the host country, with corporate tax filing consequences. Employers who have not thought this through tend to revoke arrangements suddenly when their accountant flags it.
• Will your benefits continue? Group health insurance, disability coverage, and retirement plans often have territorial limits. Most Canadian benefit plans do not cover medical care abroad beyond emergency situations.

06.One bonus item: what happens if it goes wrong

If you are terminated while working abroad, the question of which country's law governs the termination becomes genuinely complicated. Your Canadian contract may say Ontario law applies. The host country may say its own termination rules govern because the work was performed there. Tribunals in both countries may take jurisdiction. The legal costs of resolving the conflict can exceed the severance at stake.

This is why the arrangement should be documented in writing before you go, not after. A short addendum to your employment agreement confirming the location, duration, governing law, and what happens at the end of the arrangement is the single most valuable document you can have. Most employers will sign one if you draft it. Most do not think to ask.