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With the help of Bonnie and Kai, Damon and Elena set forth a plan to rescue Damons mother Lily, who is trapped in the 1903 prison world. Meanwhile, when Carolines plan for Stefan backfires, she is left to pick up the pieces. Elsewhere, back at Whitmore College, Enzo and Alarics attempt to reel Caroline back in doesnt quite go as planned when they realize theyre outmaneuvered. Lastly, an unexpected gift from Bonnie leaves Damon shaken to his core.