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Am I able to combine the Sneak Attack (Rogue 9) and Volley (Ranger 11) class features to basically create a wall of arrows and death while hidden inside a bush, sneak attacking a mass of enemies, and get automatic criticals from Assassinate?
I've read pages 90–93, 95–97 of the D&D 5e PHB.
Yes, you can combine Volley with Assassinate, but not fully with Sneak Attack.
Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack (PHB 96 on Sneak Attack)
Volley only lets you make multiple attacks with a single Action. It does not let you bypass the once per turn limitation of Sneak Attack. You can only add the bonus damage to one of your hits.
You have advantage on attack rolls against any creature that hasn't taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a criticai hit. (PHB 97 on Assassinate, emphasis mine)
This feature has only one limitation: that the target did not have a turn yet. If you have multiple attacks, each of them will benefit from this feature if your target has not acted yet.
Sneak Attack
[...] Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll. The attack must use a finesse or ranged weapon.
You don't need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn't incapacitated, and you don't have disadvantage on the attack roll.
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Volley
You can use your action to make a ranged attack against any number of creatures within 10 feet of a point you can see within your weapon's range. You must have ammunition for each target, as normal, and you make a separate attack roll for each target.
You can only Sneak Attack once per turn. With you volley, you would either require advantage on the attack OR another enemy of the target standing 5ft next to it to apply Sneak Attack.
So, you can combine it, if the conditions of Sneak Attack are fulfilled, but only on one target!
