Yes, we have encountered this before when he was coming here for a visit, and his boss had given him paid time off. He is always asked if he intends to work when here. He has never been denied though, at immigration he has shown things such as proof of a return flight, communication from his boss approving paid time off, the fact that he has property in the UK, and also he has even printed bank statements to prove he has enough money to support his time in the US without earning additional income. He worked remote before it became as common with COVID, it always seems to raise some suspicion at immigration so he comes prepared.