S6, E17: With the help of Bonnie and Kai (recurring guest star Chris Wood), Damon and Elena set forth a plan to rescue Damon’s mother, Lily (recurring guest star Annie Wersching), who is trapped in the 1903 prison world. Meanwhile, when Caroline’s plan for Stefan backfires, she is left to pick up the pieces. Elsewhere, back at Whitmore College, Enzo and Alaric’s 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.