Approved a summer in Lisbon and spent the rest of it on calls with our lawyer

We’ve been remote-first since 2021 and I’ve never had a reason to second-guess it, so when one of our team asked to spend the summer working from Lisbon, I approved it the same day and didn’t think twice until our accountant came back with a question about her tax situation.

Turns out she’d crossed the threshold where Portugal can claim tax residency, we have zero legal presence there, and apparently one person working a couple of months from Lisbon is enough to create a permanent establishment risk.

Two other people have the same plans and I’ve already said yes, so this isn’t a one-off..
We sorted her employment side through an
EOR (Workmotion for her and probably Deel for the others), but the tax piece is still separate, with our lawyer working through it.

Still working through it and have no idea how we’re going to handle the other two people who’ve already said yes.