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Message: <blockquote data-quote="Monk55" data-source="post: 6691207" data-attributes="member: 6800273">Trying to stay within the rules as written, please tell me where I'm wrongFirst, we have the assassin, stealthing merrily along until he meets up with a target. The assassin attempts to stay stealthy/hidden and makes a stealth roll. The stealth roll exceeds the passive perception score of the target. The assassin is stealthy/hidden. Then the assassin declares an attack. At this point, the DM decides who is surprised. Since the assassin is stealthy/hidden and the target failed to notice him, the target is surprised. Those surprised cannot move or act on their turn, but they can react after their turn. Everyone rolls initiative, including those surprised (I would interject that as DM I would award advantage on the initiative roll to the assassin for being stealthy/hidden and disadvantage to the target for not noticing the assassin). If the surprised target wins initiative, then the assassin's attack roll will not gain advantage from assassinate, since the target will have already taken a turn in combat (in spite of the fact that the target could do nothing on that turn). As far as I can tell, anytime prior to the attack the target is surprised. Winning initiative does not negate surprise. Nothing in the rules negates surprise except a successful or failed attack. So on a successful attack roll (remember, the assassin does not have advantage on the attack roll from assassinate, however, he should probably be given advantage because he is invis and that condition gives advantage), the assassin would auto-crit, since the target is surprised, even if the target wins initiative over the assassin.</blockquote>

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