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Message: <blockquote data-quote="redrick" data-source="post: 6677034" data-attributes="member: 6777696">Hmm, wait so you are ruling that the Drow is surprised — by the Bard — but not by the Wizard?This issue came up in conversation, though never in practice, at my table when a player rolled up an Assassin. Can an Assassin "surprise" the target, even if other players have already entered combat? And, the short answer, by the rules and by my ruling is, absolutely not. A character is either surprised or not surprised. There's no "surprised by..." Otherwise, the assassin can sneak alongside a group of adventurers clomping along in heavy armor, obviously alerting their prey, but jump out and say, "But I surprise!" That's not how the rules work. Otherwise, how do you handle taking or not taking actions on your turn? When the target is alerted, they don't have to know the exact makeup and position of the attacking force, just that somebody is coming and they should prepare for combat. The hidden attacker would still get Advantage for attacking from hiding, and sneak attack if a rogue, but no benefits from being surprised. This forces a party to make a choice — send the Assassin up ahead to take advantage of a sneak attack, but risk leaving that Assassin exposed without heavily armored backup, or send the whole party forward in a full frontral assault.However, I did house-rule the following exception. If two parties are engaged in combat, and a third enters combat, from hiding, and from an entirely different direction, where the target would not be paying any attention, the target can be considered surprised with regards to that third party. This would bring Assassinate into play, and also mean that the target can take no actions against said third party for that round, nor reactions until the end of their turn. I also made it very clear that this would be awarded entirely at my discretion. It never actually happened in play. The one time the Assassin tried to pull it off, the Ranger swept around so that she was line of sight with the target and where the Assassin was hiding, and then fired, drawing the target's attention in that direction. (I think she had a good reason to do this, but it did cause some heated conversation between the two of them.) In retrospect, I probably wouldn't use this house rule again, as I don't know that there's any need to encourage even more Lone Wolf behavior from Assassins.</blockquote>

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