Introduction
For those who navigated the corporate world during the COVID era, the concept of “work from home” is nothing new. In 2025, a new reality is beginning to emerge: the “work from anywhere” (“WFA”) Era – where employees aren’t just working remotely but are also working across borders, time zones, and tax jurisdictions.

The WFA concept has moved from a niche perk to a mainstream policy in many industries. With employees seeking greater flexibility and companies leveraging global talent, the rise of digital nomadism and remote work across borders is accelerating.
While WFA arrangements have major advantages, such as greater talent pools, higher rates of recruitment, and increased employee satisfaction and retention, they also introduce complex legal and tax challenges that employers can’t afford to ignore.
In this post, we explore some of the key employment law, tax, immigration, and cybersecurity concerns that every employer should consider before implementing a WFA policy.
It’s important to note that this list of considerations is not conclusive – every arrangement has its nuances, and we encourage you to consult your legal and tax professionals before making any decisions.
1. Employment Law Compliance Across Jurisdictions
Say your employee, based in Toronto, wants to work remotely from Spain for 6 months. Which country’s employment laws apply – the jurisdiction outlined in the employment contract, or the jurisdiction they’re physically working in?
Spoiler alert – the laws of the jurisdiction where work is being performed often (but not always) take precedence. This means employers must be mindful of the local labour laws wherever their employees are logging in from.
When employees work remotely from different provinces or countries, employers must consider how local employment laws impact:
- Minimum wage and overtime laws: Some jurisdictions have different pay structures, which may require wage adjustments.
- Statutory benefits: Vacation entitlements, sick leave, statutory holidays, and parental leave policies vary widely by jurisdiction.
- Termination rights: Notice periods, severance pay, and dismissal protections differ by region. Even the most enforceable termination language in an employment contract could be undermined by another jurisdiction’s entitlements upon termination.
- Health and safety obligations: Remote employees are protected under workplace safety laws, requiring employers to ensure ergonomic work setups and safe work environments.
🚨 Potential Pitfall: Failing to consider local employment laws of an extra-jurisdictional WFA location may introduce major unexpected obligations (and costly considerations) for employers.
✅ Employer Tip: Ensure compliance with both the employee’s home jurisdiction and their remote work location. This approach minimizes legal risks and ensures alignment with global labour standards.
2. Tax Implications and Corporate Liability Risks
One of the most significant challenges of WFA policies? The highly complex and nuanced characterization of reportable income and taxation. And the concern is not just for employees – employers can get caught in international tax traps if they’re not careful.
Employers must consider:
- Payroll tax obligations: If an employee works in a different province or country, the company may need to withhold and remit payroll taxes in that location.
- Corporate tax exposure: If an employee’s remote work creates a “permanent establishment” of the business in another country, the company may be subject to local corporate taxes and laws.
- Social Security & benefits contributions: Some jurisdictions have mandatory social security contributions and requirements, which could increase employer costs.
🚨 Potential Pitfall: A business with even one remote worker in another country may unknowingly trigger corporate tax obligations, leading to hefty fines.
✅ Employer Tip: Consult a tax advisor before allowing employees to work internationally—even temporarily—to avoid unpleasant surprises.
3. Immigration and Work Authorization Issues
Not all WFH employees can pack up their laptops and head to another country. Many countries require proper work permits or visas, even for temporary or remote work arrangements. Some key employer concerns include:
- Work visas or permits: Some countries classify remote work as employment within their boards. This means your employee could be violating immigration laws without proper work authorization and documentation.
- Tax residency considerations: Employees staying too long in one country may unintentionally trigger personal tax residency obligations. This could create tax obligations for both the employee and the employer.
🚨 Potential Pitfall: If an employee overstays their welcome without the right visa, both the employee and the employer could face fines.
✅ Employer Tip: Set a clear policy on how long employees can work abroad and require verification and consideration of local visa and tax requirements before booking a long stay.
4. Data Privacy and Cybersecurity Compliance
With employees logging in from coffee shops, Airbnbs, and co-working spaces across the globe, cybersecurity and data privacy risks are skyrocketing. WFA arrangements introduce additional cybersecurity and data privacy risks, including:
- Cross-border data transfers: Laws such as the GDPR (Europe) and PIPEDA (Canada) regulate how employee and customer data is handled across borders.
- Cybersecurity risks: Public Wi-Fi = Hacker’s Delight. Employees connected to unsecured networks could expose sensitive company data or access to cybercriminals.
🚨 Potential Pitfall: A company could be liable for a security breach if its remote employees don’t follow strict cybersecurity protocols.
✅ Employer Tip: Require VPNs, multi-factor authentication (MFA), encrypted devices, and company-approved security measures for all remote workers.
5. Crafting a Legally Sound ‘Work from Anywhere’ Policy
If you or your company wants to offer WFA flexibility, a formal WFA Policy is a must! Among other key considerations, here’s what it should include:
- Approved locations: Clearly define where employees can and cannot work based on legal, tax, and security risks.
- Tax and compliance responsibilities: Outline who is responsible for reporting income, payroll, and tax obligations.
- Work authorization limits: Set time limits for international work to avoid visa and tax residency issues.
- Cybersecurity requirements: Mandate VPNs, secure networks, and company-approved devices for remote access.
Final Thoughts: WFA… within reason.
Giving employees the green light to work from anywhere? Amazing. Accidentally setting up a tax presence in a foreign country? Not so amazing.
A little planning today can save a lot of legal headaches tomorrow.
While WFA policies are appealing for attracting and retaining top talent, they come with significant legal and tax complexities and considerations. Employers must take a proactive approach by aligning employment contracts, tax policies, and cybersecurity measures to ensure compliance.
Thinking about updating your remote work policy for 2025? We can help you navigate the employment law considerations.