During Day 5, Jack Bauer, with the help of CTU analyst Chloe O'Brian, infiltrated Wayne Palmer's penthouse to search for evidence of who framed Jack for David Palmer's assassination.
The authorities were notified of Jack's presence at the scene. Just as Jack escaped to his van, Jennings and several other agents began a search of the parking garage. Agent Jennings called for Bauer to show himself, but Chloe sped the van out of the garage. Jennings was among the agents who chased after her, and Chloe was quickly stopped. After ordering her to get out of the van, Jennings had his men search the vehicle, only to find that Bauer had escaped. After LAPD officers Moreno and Powell took Chloe to Jennings, Jennings called Bill Buchanan at CTU, who instructed the FBI agent to bring Chloe back to CTU.
Jennings and another agent entered the holding facility and took Walid to a nearby restroom. He and the agent acted hostile toward Walid, which made the other inmates sympathize with the latter. While in fact, it was only a cover to place a wire on Al-Rezani. Jennings then showed Walid a PDA displaying the name "Abu Fayed," and told him to feign allegiance toward the terrorist mastermind.