Cunnings was a pawn of a conspiracy plot by Daniel Shaw and Clyde Decker to destroy Chuck Bartowski and his spy firm, Carmichael Industries. She is known for her extended torturing skills, although she "prefers to think of it more as an art form". Her favorite interrogation technique has been electrocution with a device she dubs as "The Toy".
Cunnings planned on using Ellie and Awesome as leverage in order to get the Omen Virus that was recovered during "Chuck Versus the HackOff" by Team Bartowski, and the thought of his family being harmed sent Chuck into a protective yet irrational mode, falling back on his previous behaviors, instead of letting the team come up with a plan of action to get the Awesomes back. Chuck went out on his own to free his family which ended up backfiring because Cunnings got her hands on the virus and unleashed it. She was about to kill Awesome and Chuck when the rest of Carmichael Industries swooped in. Sarah was not too happy with her husband going on the rescue mission solo.
While in captivity at Castle, Robin reveals to General Beckman that she is indeed part of a conspiracy against Chuck - but has no knowledge of who the mastermind is. To getting this info, she is ironically interrogated using her own torture device.
Cunnings was incarcerated by the CIA.
Chuck: I can handle anything you throw at me.
Robin Cunnings: They all say that - so sad. [to her men] Bring out the Toy!
Chuck: Whoa, whoa. Really? That's the Toy? I don't think children should be involved with that in any way shape or form.
- Agent Cunnings is played by Rebecca Romijn, who is known for having portrayed Mystique in the first three films of the X-Men trilogy.
- At 5'11" Rebecca Romaijn was delighted to join “...such a great cast! Such a tall cast which is great for me! I'm glad I'm here to finally round out the tallest cast in Hollywood.”