Nope, unless your country has a special arrangement with the country you are visiting, you cannot work with a tourist visa, at all. Does not matter if the company is local or not. No work visa = no work.
I hope you're being sarcastic here, no?
Once again this has been reviewed by laywers at different companies who have deemed this risk to be acceptable.
There might be countries that will arrest you if you read your corporate mail while on holidays, however, these generally not on the green list of safe countries to travel too.
Acceptable to the company. That doesn't necessarily mean that it's acceptable to you, especially if penalties would primarily fall on you for illegally claiming the wrong immigration status.
Allowing unrestricted access to your country by remote workers will have economic impact.
There are several ways tax codes can categorize income:
- the country the person was hired in (e.g. US)
- the country for whom the work is complete for (say if US employee delivered code for a Canadian office)
- the country the company who hired the person is located in
- the country the company paying the employee is located in
- the country the person was originally hired in (same as #2)
- the country where the work is actually done
A lot of countries just look at the last one. Doesn't matter if you were hired in the US, paid in the US dollars and US taxes are taken from your pay check. If you complete your work in country X, country X wants their taxes according to their laws.
There is a separate aspect for the company. You as an employee might comply with all tax regulations - hired in the US, US taxes deducted, but you file your taxes in a separate country and pay taxes owed.
But your employer may be out of compliance as well - they may need to be registered in the that country, have obligations for employer tax and social security payments, etc.
It's mostly their own obligations companies are worried about. If the employee pisses off and breaks tax law in another country, well that's on them.
But when it's a big or noticeable deal, then things come into play. US baseball players have to file Canadian taxes when they play in Canada, and if an exposition game occurs in Japan or London, taxes are filed there, too.
If you're not trying to evade taxes, and aren't making much anyway, most places don't actually do anything, but if they decided they wanted to they could.
Skirting gray areas is fine - working while on a 3 week vacation is likely not worth chasing down.
Staying in a country for 4 months knowing that after 3 months you should pay taxes, but just pretending you're a tourist? That's pretty clearly trying to evade taxes.
I hope this is sarcasm. A VPN is a technical detail that would never stand up, legally. The only situation where I can see a VPN being useful is within your own company: if they don't want you working remotely a VPN might help cover up the fact that you are. But aside from that it won't help you.
Where are you working if you are flying above various states and countries while VPNd?
A better analogy would be if you worked remotely from a boat on the high seas on your own boat.