This is a missable achievement in Episode 2 of Trials and Tribulations, titled "The Stolen Turnabout".
You'd need to examine two or three items that are connected to the legendary security guard, Wendy Oldbag. This achievement, when it was first released in the iOS, was glitched in such a way that even though the achievement description revealed exactly which items to examine, the achievement wouldn't unlock. Instead, another item not mentioned in the description was the trigger.
This time round, the items aren't mentioned in the description, but if you follow old guides, you'd probably not unlock it too.
So, here are the items to examine for this version of the game:
1. DeMasque's Hideout
Examine the fish tank at the back left of the room. This was part of Oldbag's security costume from a previous case.
2. Security Room at KB Security
Examine the bottom left corner of the room that has a printed pink bag of sorts. This is Oldbag's seat.
3. Security Room at KB Security
Examine the command list above Oldbag's seat - it's a white poster kind of thing that tells Larry to make coffee for her, or something. (credit to AGGY AggressoR)
The achievement should unlock once you examine these. They can all be done on Part 3: Investigation of this mission. It's best to make a save at the security room before attempting this.
PS: If all else fails, examine everything in the security room.