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Message: <blockquote data-quote="Amaroq" data-source="post: 5061337" data-attributes="member: 15470">That's exactly what I would rule, too.The PHB rule is pretty explicit: "Some battles begin with a surprise round. A surprise round occurs if any combatants are unaware of enemy combatants’ presence or hostile intentions. For example, if you fail your Perception check to notice concealed enemies, you’re surprised. Or if supposed allies spring an attack and you failed your Insight check to notice the attackers’ traitorous intentions, you’re surprised. But if any of your allies made their Perception or Insight checks, they’re not surprised.When any combatants achieve surprise, they act in initiative order during the surprise round. Surprised combatants don’t act at all during the surprise round."For your situation, I'd say you initiate the combat not by "unleashing the Cloud of Darkness", but by starting to draw a weapon/implement, etc. We roll opposed Bluff/Insight checks to see if the other NPC's are surprised; we've previously determined that only one of the PC's is "clued in", great.Say the NPC's all fail their Insight checks; you've got the drop on them.You and your PC friend roll Initiative; one of you goes first. It might even be him. Either way, that character only gets a single standard action. . . . Its kinda like a gunslinger saying "I shoot him". The surprise round actually starts when he begins reaching for his holster ... presumably he has the "Quick Draw" feat, being a gunslinger ... so his standard action in the Surprise round is to actually draw and fire his weapon. He may not successfully get the shot off before somebody else (who isn't surprised) does ... if that person rolled better Initiative than him. . . . Incidentally, if there was a tense standoff between the two hostile sides who are fully aware of each other, I'd have ruled that neither member of either party could be surprised when hostilities broke out.</blockquote>

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