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Message: <blockquote data-quote="Jediking" data-source="post: 6824719" data-attributes="member: 6803126">It depends on the situation and what the ambush is trying to accomplish. If ALL people were asleep in the wilderness, I'd probably just let the enemies ambush them. If all the PCs were in an inn and had no real reason to expect danger, that's a bit more of a 'gotcha' so would ask for a roll (although disadvantage/etc comes into play). [MENTION=12283]Illithidbix[/MENTION] has good points and that seems fair.Personally, if someone was on watch I'd count that as actively looking (paying attention/guarding) and have them make a roll against the enemy Dexterity (Stealth) check (one Stealth check for the enemy group), but using the Passive Perception is also completely logical to use. If others are sleeping, I would not even call for a roll. On a fail the ambushers would get a surprise round on everyone, then combat as normal. If the watcher managed to spot the ambushers, he could whisper or yell out a warning.I would count an elf to be watching as well. If he was staying up with another person and they were talking, maybe I'd use their Passive Perception. If the elf was in the midst of the trance, I might give him disadvantage.</blockquote>