Working remotely for my home employer while I settle — how did you handle the grey area?

You're right to think it through rather than wing it. Generally, doing work for a foreign employer while you get your long-stay status sorted is a normal situation a lot of us have been in — but the specifics genuinely depend on the country, so don't take any one person's setup as a template. Portugal has proper routes for this; the Visa section of the guide points at the long-stay options. Getting onto the right visa early saved me a lot of stress.

Totally different in the UAE — the free-zone setup made it clean for me. The lesson that travels though: find the legitimate long-stay route for YOUR country and get on it, rather than stretching a tourist entry and hoping.

Careful, sensible question. Honest general answer: working for a foreign employer while you regularise your stay is usually fine — but "usually" is carrying a lot of weight, because the rules are country-specific and they change. The Visa section of your destination guide is the place to check the actual long-stay / nomad-visa options rather than relying on forum anecdotes, mine included. If you're staying long term, a proper long-stay visa is worth it for the peace of mind alone.

I overthought this for months and the fix was one paid hour with an immigration adviser. Cheapest anxiety cure I've ever bought — they told me in 20 minutes what six forums couldn't agree on.

Seconding "get on the real visa." The tourist-entry stretch works right up until it very much doesn't, and a border is a bad place to learn where the edge is.

OP — thank you, this is exactly the reassurance-plus-reality-check I needed. Booking the adviser hour and reading the Visa section properly this weekend.