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Message: <blockquote data-quote="Chaosmancer" data-source="post: 9429171" data-attributes="member: 6801228">If the DM decides the Ruffian is not taking the search action, then it would be passive instead of rolling a d20. This is also why the DC 15 is there, to give a baseline for when you don't want the target to roll. I don't know why the ruffian's reaction or action matter here, what matters is what the rogue is doing next. If the rogue just wants to slip past the ruffian, then unless the ruffian is standing in the doorway the rogue wants through the Rogue can dart from cover to cover and get past the Ruffian into the next area. If the Ruffian has a high enough passive to spot the rogue, well, Surprise and/or initiative might be appropriate, but it depends. IF the rogue decides to tell the Ruffian he has a message for the boss, and deceptions his way past, there would be no need for initiative. If he wants to just stab the guy, initiative. You haven't entered into turns yet, so no one has taken any turns or actions in the turn order yet. Initiative would determine what was happening next, but I would not give the rogue surprise or the invisible condition, because combat is starting due to them being spotted.</blockquote>