I told the player that it's up to him if he wants to be stealthy or not, but if he doesn't roll then the others might get suspicious of him. So he decided to roll (and rolled a 1, lucky).
My point with the rolls was that for me, the moment someone wants to be stealthy, he rolls stealth (unless I determine it's impossible or trivial to be stealthy, which is definitely not the case here). For me the result of this roll is also used to determine if surprise is successful, but a successful stealth roll in the context still does not lead to surprise being successful, which I think is reasonable. What I found weird is that iserith said he would not even roll for stealth, but I think hiding should be possible, even if surprise is impossible.