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Hrm!  So, after Petra tells you about the intruder, you can either tell her to watch the cameras to try to narrow down where he'll be, or you can tell her to go to whichever location you think he'll be at, and lay a trap.  If the first place you tell her to go ("Watch the gym") happens to be where the intruder turns up, then that should trigger the achievement.  If you're wrong (he was actually at the Office that night, instead), then it's not your first try anyone, and you don't get the achievement.

Does that match up with what you did?   The very first time you actually told her to go watch a specific location, he happened to be at that location that night?

Yep, told Petra to watch R&D the first time (I did reload a save tho) when I was prompted and was told the next day the intruder was caught, visited the Sec Office and did the whole thing until the transformation. Still nothing.

I even went for a second playthrough after my first and in the middle of some casual fourth-wall breaking Mason mentioned I did have the achievement, checked but it's still greyed out.

Hmm! We'll look into that one. There is a cheevo for transforming him as well (and that's the one that the skip uses), but it should go off if you get him on the first shot. We'll check it out!