Simon invites Annie to accompany him on his business trip to Cuba. She asks Lena for permission to go. While Lena couldn't authorize the trip, she encourages Annie to use her vacation time and helps her get a passport. In Cuba, Annie tracks Simon to a Cold War era listening site and reports her finding to Lena. Simon's business associate, Hector, is suspicious of Annie and he knows about Danielle. Annie and Simon make passionate love after deciding to leave the next day. Before leaving, Simon and Hector take Annie to a factory. Instead of killing Annie, Simon slits Hector's throat. Annie and Simon part ways at the airport.

Joan is suspicious about Annie's sudden vacation and approaches Lena about it. Lena denies any knowledge of Annie's whereabouts, but Joan doesn't buy it.

Auggie believes that Jai's father, Henry Wilcox, knows more about Jai's death. Auggie visits Henry in prison, but he refuses to talk. Auggie is persistent and returns again. This time, Auggie is able to get through to Henry, who reveals the location of Jai's safe house.

Arthur continues in his quest to be named Ambassador to China. Joan comes around on the idea and offers to host a dinner party for an influential Senator. When the Senator suggests that Arthur is a shoo-in for the post and it's the perfect time to get out of the CIA, Arthur explodes. He doesn't want to leave his mess for another to clean up.

Annie makes it home and meets with Lena. Lena reveals that Simon is in love with Annie and they can now use that to make him do what they want. Annie didn't seem to like that idea.