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Message: <blockquote data-quote="iserith" data-source="post: 7231619" data-attributes="member: 97077">No, that would be just the one Dexterity (Stealth) check. I don't see a reason to roll twice.Your situation is different though because of the specific context. I would rule no surprise is possible (and there is no ability check), but gaining the benefits of hidden (to the extent the environment allows for it) might be an ability check. I would likely not separate it out this way though. I don't see any upside to the play experience for making things more complicated. Whether the PCs succeeded on the ambush they're trying to lay would, in my ruling, probably be tied to how the infiltrating PC did on his or her tasks with success meaning the PCs get the jump on the monsters later when said PC leads them into the ambush.</blockquote>