Clearly the lowest profile movie on this list, but a couple of well-known physical security measures (and attempts to circumvent them) earned it a spot. Protagonist Milo Hoffman, working for a company called NURV, intentionally gets himself nabbed by security chief Bob Shrot as he conspicuously tailgates another employee, who was going into a restricted area of the building and had swiped his RFID badge. While Hoffman is detained in Shrot's office, a makeshift explosive that Hoffman planted in a broom closet earlier goes off. As alarms begin to wail, Shrot bolts from his office, leaving Hoffman behind, to go investigate.
Hoffman then executes his intended plan, which is to duplicate a badge -- belonging to an employee with higher access privileges than himself -- and tamper with the video surveillance watching over the mysterious "Building 21" on another part of NURV's campus. He switches out the live feed for archived feed so when he breaks into Building 21 later that night, it will appear on the monitors that all's quiet.
The embarrassing part here isn't so much that Hoffman switched the feeds and got away with it, as it is a somewhat plausible scenario (though it is unlikely that a guard even slightly paying attention wouldn't notice the he's watching archived feed). Rather, the bigger issue here is that Hoffman was left unattended in the office of the head of security after he was just caught for violating security protocol. Oh, and Shrot made sure that important security software that provides access to both badge creation and video surveillance was left open on his computer before doing so.