Employers hoped remote work would vanish with the pandemic. Employees quietly built their lives around it. Courts, meanwhile, have started defining its legal boundaries — often in ways employers never anticipated.

Across Canada, companies pushing sudden return-to-office mandates are colliding with employees who now view remote work as a contractual right — and in most cases it is.

Surveillance software has become the new battleground. Documentation — or the lack of it — is deciding dismissals. And judges are increasingly skeptical of employers who change major work terms without explanation.

This three-part package explains:

•Why remote workers keep winning in court
•How employers can stop losing these cases
•How employees can protect themselves and assert their rights

Remote work is not dying. It is maturing into one of the most consequential employment law fronts of this decade.

Canadian employers made one colossal mistake during the pandemic: they assumed remote work was a temporary indulgence. Courts took a very different view. They treated remote work as a bona fide employment term — one that employers now ignore at their legal peril.

And that is why, across the country, remote employees are quietly (and sometimes not so quietly) winning lawsuits. Not because judges prefer the work-from-home arrangement, but because employers keep forgetting the basics of employment law.

Let me explain.

Employers insist that "the office is where the magic happens," and order workers back to their desks. Legally, their rationale, however sound from a business standpoint, is totally irrelevant.

If an employee has worked remotely for a considerable period or was hired on the understanding that the job was remote, courts have repeatedly held that employers cannot unilaterally revoke that term. Doing so fundamentally alters the employment contract and triggers a constructive dismissal.

Some employers seem stunned when they learn that even a partial change — three days in the office instead of zero — can be enough of a trigger to create a constructive dismissal. But if location is integral to the bargain, which it generally is, altering it without consent is unlawful.

The argument that "everyone must return" does not revoke contract law.

In the rush to manage teams they cannot physically see, employers have embraced surveillance software with religious zeal.

Keylogging. Webcam activation. Mouse-movement analytics. Automated productivity scoring.

It has backfired.

When a discipline or termination decision is based on opaque algorithmic tools, courts are skeptical. Judges want human reasoning, not a dashboard.

Employers cannot explain how the software works, how it calculates "performance" or whether it captures context.

That lack of transparency creates a litigation gift for employees.

Never in history have employees documented their working lives so thoroughly. Remote workers save emails, Slack messages, Zoom captions, screenshots and task logs.

Documentation wins cases.

Most constructive dismissal and wrongful termination disputes come down to whose version of events a judge believes. Remote employees now arrive in court with a digital archive. Employers often arrive with… nothing.

"Performance issue."

"Poor communication."

"Lack of engagement."

Courts want proof. Employees provide it. Employers do not. The result is predictable.

Here is the most consistent pattern:

Employers are firing remote workers without warning, without progressive discipline and without contemporaneous records.

In the office, managers naturally document conversations. Remotely, they often forget. Out of sight is too often out of mind.

Instead of structured performance management, they send vague emails and then terminate for cause — a strategy which never survives judicial scrutiny.

If employers cannot prove that they coached, warned or even spoke to the employee, the court treats the termination as without cause — and awards lengthy notice, plus additional damages for asserting cause in bad faith.

Canadian courts quietly apply a "reasonableness lens" in employment matters.

Remote workers often appear more reasonable because they are:

• willing to work,
• performing adequately enough,
• following the rules of the arrangement the employer created or at least agreed to.

Employers, meanwhile, often look arbitrary when they reverse remote policies overnight.

Courts don't reward arbitrariness.

The result: remote workers keep winning — and will continue to.

Employers are losing these battles not because remote work is sacrosanct but because they misunderstand their legal obligations.

They treat remote work as an optional perk. Courts treat it as an enforceable term.

They use surveillance tech as a shortcut. Courts treat it as unreliable.

They terminate without procedure. Courts call it wrongful dismissal.

Unless employers fundamentally rethink how they manage remote employees — with proper contracts, documented expectations and real performance management — they will continue to lose.

Remote workers are not winning because they are remote. They are winning because employers are mishandling the law.

The courts have noticed.

Howard Levitt is senior partner of Levitt LLP, employment and labour lawyers with offices in Ontario and Alberta, and British Columbia. He practices employment law in eight provinces and is the author of six books, including the Law of Dismissal in Canada.