Strahd vs. Pale Horse & Co.
Sneak Attacks, How do they work
There were some questions about when a sneak attack can be performed, including ranged vs. melee.
Kelley did some research and I will summarize here and make some rulings.
Here's the final ruling, and below my explanantion:
Sneak attacks can be performed by a rogue in 2 broad circumstances:
1. When an enemy of the target is within five feet of the target and is not incapacitated, and the rogue does not have disadvantage for some reason. (note it is an enemy of the target, not necessarily an ally of the rogue).
2. When the rogue would have advantage on the roll anyway.
Commonly used advantages are:
- When the rogue is flanking an enemy (this would invoke Rule #1 anyway).
- When the rogue is behind the enemy and the enemy cannot turn to face him (has already used its reaction).
- When the rogue is Hiding (this can only be done once before the rogue must break line of sight and Hide in a new spot).
So Rule #1 is pretty simple, but the 2nd can be tricky, especially in the last condition re: Hiding. If you attack from a hidden position, then you get advantage. If a rogue hides, and attacks, then he should get advantage and thus a Sneak Attack opportunity.
However, this could lead to, say, the rogue finding a boulder, ducking behind it on a bonus action (after they get Cunning Action) and attacking from that spot the same round. The first time this happens, this is fine, but it seems silly for the rogue to keep ducking behind the same spot every turn, and the enemies somehow are unaware of where he keeps going even after they seem him pop out from the same rock over and over and over.
Thus I am inclined to limit Sneak Attacks to only when the enemy cannot see, or is not looking at, the rogue at the time of the attack. So popping out from cover in the line of sight of the target, and/or from a spot previously used, does not give a Sneak Attack nor advantage. Using cover still confers defensive advantages, so the pop in and out thing is still useful.
If you can get to a new spot away from the target's facing without being seen, and pop out from there, then you're good. So, (given Cunning Action) you can hide behind a boulder (bonus), move with a successful Stealth check to a new boulder (move), and pop out, then you'd get a Sneak Attack (attack/normal action).
It is important to note that none of this is necessary if the enemy is fighting with someone else in melee range, because then you will be invoking Rule #1 and you get a Sneak Attack anyway.
My logic (I hope) can be best illustrated by imagining just the rogue and just 1 enemy in a room with some cover objects. It doesn't make sense that if the rogue ducks behind cover and the enemy sees him and knows he is right behind that desk that if the rogue pops out, and the enemy sees the whole thing, he gets a sneak attack.
However, if the rogue can somehow fool the enemy into thinking he is behind the desk, but he is really somehow behind the curtain, then you get a sneak attack. Or, if the rogue goes behind the desk, Stealths behind the bad guy without it seeing, and then attacks, he get a SA.
For Merric's case specifically, this becomes pretty easy, because he can hide behind cover, pop his hood on, get advantage on the Stealth check to move to a new spot or behind an enemy, and then Sneak Attack. Note – moving while stealthed cost double move points.
And one more time, if you are attacking a target that is already engaged, none of this matters because of Rule #1.