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Message: <blockquote data-quote="Planesdragon" data-source="post: 1686750" data-attributes="member: 11133">Surprise is usually handled by DM's judgement.  However, there are two important things to note:  1: Each character in a combat is essentially surprised until they take their first action--they're "flat footed."   A rogue that gets initative on someone can start the fight with a sneak attack, even if it's just throwing a dagger at the enemy wizard from 30 feet away.  2: "Surprise rounds" are often best done by use of the Listen skill.  Barring no other situations, a DC 5 for each quiet party (-1 per member) Listen check should be enough to notice them.  Only those that roll poorly will fail--and if the other side is talking or fighting, the base DC would be 0--meaning that, barring exceptional concealment or distance, there wouldn't be any chance of failure.  You could also have the PCs and the NPCs make opposed listen checks, with the highest roll being the first to notice the other side.</blockquote>