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Message: <blockquote data-quote="DEFCON 1" data-source="post: 7231538" data-attributes="member: 7006">For me, I'd look at the narrative story of the situation to figure out what the intent is, and then only apply any rules if there's a question.So if the party of PCs have made the plan "So-and-so will go to the enemies and bring them back to us so we can ambush them..." the characters who stay back know that when So-and-So returns, he's going to have the enemies with him (unless of course he just walks back casually and calls out "It didn't work guys!  They aren't here!" or whatever).So no... when the remaining party sees So-and-So return, they have prepared their ambush for the enemies.  They are not Surprised because the purposes of this encounter, So-and-So is a member of the other group.  Now as was mentioned above... if the enemies were trying to sneak along as they traveled just in case, they would get to make DEX (Stealth) checks (either individually or as a group depending on how the DM chooses to rule it) and those are compared to the party's Passive Perceptions.  By the same token... the party of PCs would probably also make DEX (Stealth) checks (again, either individually or as a group) and those would be compared to the enemies Passive Perceptions.  Although in this case... if the enemies Passive Perception was less, then they WOULD be Surprised for the first round, because they weren't expecting So-and-So to be leading them into an ambush.So in my ruling as the DM... once initiative is rolled, the PCs get to go in the 1st round regardless, because they are not surprised (having seen So-and-So and knowing he's brought the enemies with him.)  Any enemies whose PP was higher than any party member's Stealth check are also not surprised, and would also get to go in the 1st round.  And then finally... once each party member and enemy has chosen their target for the 1st round, I'd compare each Stealth check of the attack versus the PP of the target, and anyone whose Stealth was higher would get Advantage on their attack due to being Hidden.(And as an addendum... when comparing Stealth checks to PP, because the PCs have more knowledge than the enemies do that ambushes are nearby-- because So-and-So is the red flag telling the PCs the enemies are here-- I probably would have the enemies receive Disadvantage on their Passive Perception to denote the difference.  It's not necessarily necessary to do this, because the bonus the PC are already getting is that some enemies are going to lose their 1st round due to Surprise anyway... but if the ambush is really that good or So-and-So did a fantastic job in setting the enemies up (say perhaps a really good Deception check), then maybe I'd give that additional bonus to the PCs so that even more enemies will end up Surprised.)</blockquote>

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