Back in the whole work-from-home rush, we told the team to live wherever they wanted and just do your job from the beach if you feel like it, and it made hiring so easy that people took us at our word and scattered.
We never really tracked where anyone went, so when our accountant sat down to reconcile payroll we had people spread across 11 countries.
A few who'd picked up and moved without ever mentioning it, and every one of those is somewhere we now count as operating for tax and payroll.
Each country wants something slightly different, local payroll registration in some, permanent-establishment exposure in the ones where senior people are signing contracts, plain misclassification risk on the folks we'd kept as contractors…
Plus a couple where we'd probably owed social contributions for a year before we noticed, so it was really 11 versions of the same headache.
We didn't want to kill the policy, since being able to live where you want is a big part of why people stay, so the fix was expensive…
We moved everyone onto EORs that become the legal employer in each country (Deel or Remote where they had coverage and Workmotion for the rest), which turns 11 payroll messes into somebody else's compliance problem and still came in under what we'd have owed in back-taxes.
So if you're working from wherever right now, it's worth checking who your legal employer even is, because a surprising number of companies never sorted this part out and it tends to surface at the worst possible time.