With the help of Bonnie (Kat Graham) and Kai (guest star Chris Wood), Damon (Ian Somerhalder) and Elena (Nina Dobrev) set forth a plan to rescue Damon's mother Lily (guest star Annie Wersching), who is trapped in the 1903 prison world. Meanwhile, when Caroline's (Candice Accola) plan for Stefan (Paul Wesley) backfires, she is left to pick up the pieces. Elsewhere, back at Whitmore College, Enzo (Michael Malarkey) and Alaric's (Matt Davis) attempt to reel Caroline back in doesn't quite go as planned when they realize they're outmaneuvered. Lastly, an unexpected gift from Bonnie leaves Damon shaken to his core.
