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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?

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  • \$\begingroup\$ I had assumed you were talking about surprise rounds at first, but I'll make a note anyway that you cannot get multiple surprise rounds. In case anyone else makes that assumption. \$\endgroup\$ – Premier Bromanov Oct 12 '15 at 19:33
  • \$\begingroup\$ @LegendaryDude We don't generally close older questions as duplicates of newer questions unless there's a really good reason. \$\endgroup\$ – Miniman May 17 '16 at 23:10
  • \$\begingroup\$ @Miniman Yep, I didn't see that this one was the older of the two until I had flagged it. This one came up in the activity feed and I assumed it was recent. \$\endgroup\$ – LegendaryDude May 17 '16 at 23:13
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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.

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    \$\begingroup\$ Addendum: If the rogue didn't moved, he can hide again, but the enemies will remember where he was when he "disappeared", and probably will be the first place they will check. It is not magic amnesia like in Skyrim (i.imgur.com/hdnr031.jpg). \$\endgroup\$ – Nibelung Oct 13 '15 at 2:19
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    \$\begingroup\$ I think it'd be worth specifically referencing "Unseen Attackers and Targets" (PHB5e pp.194-95) and the sidebar "Hiding" (PHB5e p.177): they argue that the re-hiding would be rather difficult and is to be adjudicated by GM, not necessarily a straight stealth vs. perception roll-off. \$\endgroup\$ – nitsua60 Nov 21 '15 at 2:59
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    \$\begingroup\$ In addition to sending a minion out to the last known location of the hidden rogue, have a couple of enemies ready an action to attack as soon as the rogue reappears. \$\endgroup\$ – LeHill Jul 19 '16 at 18:28
  • \$\begingroup\$ Jeremy Crawford touches on a similar topic here, and Mike Mearls comments on similar questions here, here, and here. \$\endgroup\$ – V2Blast Jun 6 '18 at 7:43
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I'd let him do it once, the first time during an encounter. After that, it's no longer a Sneak Attack. Despite the fact that he is hidden, the enemy is aware of his location and that he is hostile. If there were two doorways and the defender was uncertain which he might attack from, I might be more tempted to allow it.

Just disappearing from sight does not allow for advantage. From PHB Chapter 7, Hiding:

In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you. However, under certain circumstances, the Dungeon Master might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack before you are seen.

This indicates that the defender needs to be unaware of your general position in order to get advantage, and thus the sneak attack bonus. If you are firing from the only place you can fire, and the enemy knows you are there, it's unlikely that they would be surprised enough for a attack to have advantage.

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    \$\begingroup\$ Sneak attack doesn't rely on surprise. It relies on advantage and/or having an allay adjacent to the target. (PHB: p96) If you successfully hide, you gain advantage, and thus trigger sneak attack damage. If you adjudicate that the character is in fact NOT hidden, that changes the argument. \$\endgroup\$ – Ruthaford May 18 '16 at 15:30
  • \$\begingroup\$ Thanks. I've edited my answer to put the emphasis on gaining advantage, and to tie it more closely to the quoted rule. \$\endgroup\$ – keithcurtis May 18 '16 at 16:56

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