More powerful than ever, Kai holds Elena captive while he learns to control his newly acquired magic. At the Salvatore mansion, Liv and Alaric try to prepare Jo for the impending merge ceremony with Kai, but they quickly realize Jo is weaker than they thought. After bringing Sheriff Forbes home from the hospital, Caroline travels with Stefan to North Carolina in search of a cure for her mother's cancer. Meanwhile, Stefan, who has his own intentions for traveling to North Carolina, is caught off guard when Enzo shows up demanding to know what Stefan is hiding. Lastly, when Damon discovers Elena has been kidnapped by Kai, he is forced to rethink his strategy after an unexpected visitor throws a wrench into his plan.

Determined to celebrate Bonnie’s birthday, Elena convinces Jeremy that it’s what Bonnie would have wanted. After piecing the broken ascendant back together, Elena, Jeremy and Damon attempt to send Bonnie a message, but the situation turns dire when they make an unsettling discovery. Meanwhile, after uncovering Stefan’s secret about his great-niece Sarah Salvatore, Enzo enlists a reluctant Matt to help interfere with her life. Elsewhere, Stefan keeps a close eye on Caroline as she unconventionally attempts to cope with everything going on around her. Lastly, realizing it might be time to move on with his life, Jeremy contemplates leaving Mystic Falls for good.

It’s Jeremy’s last day in Mystic Falls and Elena puts on a brave face as they reminisce about their past. Stefan and Caroline find themselves growing closer as they prepare Caroline’s family cabin for her mother to live out her final days. While packing up her office, Sheriff Forbes turns to Damon for help solving one of her remaining open cases involving Elena’s parents. Elsewhere, when a violent confrontation with Enzo leaves Jeremy wondering whether he should leave or not, Matt finds his own life on the line after Enzo lures him and Sarah Salvatore into his dangerous plan. Lastly, Caroline rushes to the hospital after learning her mother has taken a turn for the worse.

After shutting off her humanity following the death of her mother, Caroline gives her friends an unexpected ultimatum. Not knowing how to handle the new Caroline, Stefan’s attempt to intervene sets off a dangerous chain of events, leaving him and Elena in a race against the clock. Meanwhile, after seeking answers from Kai about the prison world, Damon’s world is turned upside when he learns some devastating news about his mother Lily. Elsewhere, Enzo finds himself becoming increasingly intrigued by Sarah Salvatore, and Bonnie begins to struggle with the effects of being back in the real world.

With the help of Bonnie and Kai, Damon and Elena set forth a plan to rescue Damon's mother Lily, 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.

With their humanity turned off, Stefan and Caroline begin wreaking havoc at Whitmore, leaving Damon to come up with a risky plan involving Lily. After rushing to help Jo treat victims of Stefan and Caroline’s latest killing spree, Elena discovers Jo is pregnant, prompting her to reevaluate her own life as a vampire. Meanwhile, when Sarah boldly turns the tables on an unsuspecting Enzo, he is forced to open up about his tragic past. Lastly, at Scull Bar, a twisted round of karaoke leaves Tyler and Matt in a dangerous situation.

After learning that someone from Stefan’s past may be Damon and Enzo’s next target, Stefan, Bonnie and Caroline head to North Carolina. There, Bonnie takes drastic measures in an attempt to break Enzo free of whatever has a hold over him. At the Armory, Alaric and Georgie stumble upon a mysterious symbol that may be related to the supernatural force controlling Damon and Enzo. Finally, Caroline gets an unexpected surprise from Stefan.