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Message: <blockquote data-quote="Maxperson" data-source="post: 8789783" data-attributes="member: 23751">When he says he's taking the shot, he takes the shot if the target doesn't know that he is there.  Surprise  happens, initiative is rolled and the best the target can hope for is to win and turn it into a normal shot by noticing the assassin right before the trigger is pulled on the crossbow or something.  If he loses, the assassin PC gets advantage and crit if he hits.Now if the target makes his perception roll, then he knows the assassin is there prior to initiative being rolled. When initiative is rolled if the target wins, then he gets to act first as normal and the assassin might not want to take the shot on his turn.  There's no reason to hold the assassin to the action of taking a shot when it was predicated on surprise which isn't there.</blockquote>