Quote Originally Posted by NecessaryWeevil View Post
From your description of the rogue's methods, you should be rolling Deception vs Insight instead.
The surprise is not the rogue's presence, but their intentions.
Seconding on this - it's detecting the motive. Note you should also look at this initially - passive insight, unless someone questions the motive.

My other thought is Perception vs Sleight of Hand (concealing the move), but that's basically one Dex check or another.