When Kourtney and Kim discover that Khloé has been hanging out with a new crowd, they intend to dig deeper into her life. Kris and Kim's arguments about Kim's wedding causes her to move out.

Kim attempts to prove that her skills go beyond the world of beauty and fashion as she makes a speech at a conference.

Khloé travels to Napa with Kourtney and Kris, where she needs to make a decision about her divorce; Scott tries to rid himself of the alleged Kardashian Curse.

Kim, Kourtney and Khloé travel to to the once-restricted country of Cuba. Originally, they were going to watch Kendall walk in the Chanel show, but she had to drop out due to a schedule conflict. The sisters turn it into a family trip and bring Kanye, Malika and the kids along to absorb some culture. They tour the sites of Havana and are so taken by the Cuban capital that Kanye says he'd like to shoot a music video there. Meanwhile, back in Calabasas, Kris is lonely without her eldest daughters, so she focuses all her attention on Kylie. At first, Kylie feels harassed, but she comes around to enjoying the quality time with her Mom.

After an uncomfortable confrontation with her ex at True's first birthday, Khloé must figure out how to coexist with her ex. Kim accuses Kourtney of copying her style. Kim searches for answers regarding a frightening medical diagnosis.

Kourtney and Scott seek parenting advice, but Corey's input causes an argument. Khloé plans a wine-tasting trip to Napa to check in with Kylie. The family is fed up with Kim's new intense security protocol, so they take matters into their own hands.