there is no way for him to just go to the immigration office to do what he needs to do. He has to leave the country and re-enter. Immigration can’t help anyone who’s in this sort of situation.
Nadia Cristina Vecchione ok. Flying is always the better of the two. You’re less likely to be questioned. But still, they may ask you why you’re not on a proper visa. They may not say a word to you.
Nadia Cristina Vecchione by land? If so, you’re only able to do two land border bounces in a calendar year. Which I don’t think would be your case. Either way, back to back can cause problems. It all comes down to the immigration officer you’re going to face.