Cassie has settled into Middleton and is busy making a home of Grey House. Her boyfriend, Sheriff Jake Russell, and his kids are happy to have Cassie in the neighborhood, but she has yet to gain the trust of some people in town. Before long, a stranger rolls into town with papers entitling him to legal ownership of Grey House. Before she knows it, Cassie is left without a home and is convinced Middleton isn’t where she belongs. Ultimately, everyone will learn holding on too tightly to something can make it more likely that thing will slip through your fingers.

Mal struggles with her new celebrity life as the girlfriend of King Ben, putting a spell on her hair making it blonde, and maintaining a princess-like personality that she is uncomfortable with. She admits her issues to her friends Evie, Carlos, and Jay, but they are content with their new lives in Auradon and do not wish to return to the Isle of the Lost. Evie scolds Mal for relying on her mother's spell book to solve her issues. Carlos, wishing to ask Jane to the upcoming Cotillion dance, turns to Mal for help to be honest with her. Mal gives him a sweet that will make him speak the truth, but his dog Dude eats it, magically speaking the truth in English and very frankly as a result.

Ethan Wate longs to escape his small southern town. He meets a mysterious new girl, Lena Duchannes. Together, they uncover dark secrets about their respective families, their history, and their town.

The teenagers of Disney's most infamous villains return to the Isle of the Lost to recruit a new batch of villainous offspring to join them at Auradon Prep.