In our D&D 5e games, I am not sure how to handle the following situation relating to stealth:
Enemies are in a room. The rogue stays outside, stepping to the side in order to be able to hide. Now, can he attack the enemies inside the room with his bow while getting advantage and sneak attack?
In favor of sneak attacking one might say, that the enemies don't see him prepare and have little time to react to his attack.
On the other hand, they know where he is, they just can't see him.
Is the situation different with a pile of boxes, where they know he's hidden behind the boxes, but not from which end he will attack?
Best Answer
Yes, if he is truly hidden (versus their passive perception), then he will have advantage on his attack with sneak attack damage. Now, he will lose stealth when he attacks, but if he has at least two levels in rogue, then he should be able to hide as a bonus action. So if the rogue is left alone, I can see him attacking every turn (with advantage and sneak attack) followed up by hiding as a bonus action.
If his stealth roll is higher than all the monsters' passive perceptions, then they don't "know" where he is. They have suspicions, sure, but they are still going to be subject to an attack with advantage when he pops out to attack them.
As a DM, I wouldn't let this scenario play out for long. While this is what rogues do well and you should definitely allow him to do this, he needs to be challenged. After a couple rounds of him popping out and sneak-attacking things, I would send a minion or two his way. That might flush him out, and remember, if a monster is standing right next to him, he will get disadvantage on his ranged attacks.