[throwawaycuriou]

Thanks for that scenario. Those potential ramifications are significant. In that specific case, one could imagine ponying up for a steep same day ticket from Thailand to keep up the ruse. One would expect there would be innumerable psychological tolls to live this way.

What about a subtler case? You begin working as a US based employee, but after enjoying your work and proving your mettle, you take the risky choice to move abroad without informing your company? Or, you have a US based apartment but periodically for a month here and there operate abroad unannounced?

Additional wrinkle: while the expectation is more clear informally, it's not clear to me what US based employment is from a legal standpoint. Is it merely filing your taxes from a US based address?

[wallflower]

No, don't do this in any shape or form. If you want to work remote from abroad, tell them. Set expectations as to your performance and availability. Negotiate on their concerns. Don't do it on the sly. Like you mentioned, the mental overhead of lying will impact on your life. Think of it like cheating on your significant other.

In the very slight chance you are already doing this (cannot tell), you need to come clean with your boss immediately, preferably face to face.