The Saltzmans find themselves in the prison world and are confronted by Sebastian. Lizzie realizes Alaric lied to her. Alaric stabs Sebastian and then leaves to look for his crazed brother-in-law Kai Parker, who has been trapped here for years. Sebastian convinces Lizzie to explore this empty world and enjoy it to the fullest. Alaric and Josie encounter the three students Alaric and Emma also trapped here after they slaughtered a group of humans in the woods: a vampire named Jade, a werewolf named Diego, and a witch named Wendy. Anyone banished to this world doesn't stay dead, but the same isn't true of the Saltzmans. The banished students plan to make Alaric pay for putting them in this world. Kai appears to save Josie from Jade, but it turns out they're all planning on escaping the prison world together. Josie gives Kai a necessary ingredient to get out, and he leaves, planning on escaping himself. However, he learns that Josie tricked him and never had the ingredient in the first place. Luckily for him, Josie has told him all about Malivore and the monsters, so he plans to jump into the pit in this world, eager to escape no matter what. He calls Josie and tells her that she can make her own way out, provided she smashes the Mora Miserium and absorbs all the dark magic. Since she only has a few seconds to remember this before Kai leaps into Malivore, Josie throws the hourglass on the floor. Meanwhile, Lizzie has the time of her life with Sebastian, before he reveals that he plans to stay here forever and wants her to stay as well by becoming a vampire. When she refuses, he tells her that he has already slipped her his blood in the wine, so the turning process has started. Lizzie is driving back to Mystic Falls when she loses consciousness because Josie is absorbing the dark magic. Kai climbs out of the Malivore portal in the real world and meets the Necromancer.
- Big Bad Duumvirate: The ending seems to hint that Kai Parker and the Necromancer will join forces.
- The Bus Came Back: Kai, last seen trapped in an eternal hell, is back and worse than ever.
- Crazy Enough to Work: When his original plan to escape the prison world fails, Kai decides to try to jump into the Malivore pit in the prison world, hoping that it will allow him to return to the real world. Surprisingly, it works, although it's possible Malivore allowed him to return in order to use him as a tool against Hope.
- Evil Uncle: Kai Parker to the Saltzman twins. He doesn't regret killing their mother in the least and even admits he was actually trying to kill them. He has no qualms about lying to them and leaving them in the prison dimension and takes a special joy in telling Josie that, in order to escape, she has to become a monster like him.
- Fate Worse than Death: Anyone trapped in the prison dimension considers this to be the trope, as the dimension always replays the same day, and no one banished there can die permanently. Averted for Sebastian, who considers this world to be perfect, since he doesn't have to deal with the modern world's hectic life and the cacophony he hears every day due to his enhanced hearing.
- Freudian Slip: In desperation to try to convince Lizzie to stay with him, Sebastian calls her "Cassandra", making her realize that she was always a stand-in for his lost love.
- Gone Horribly Wrong: The party in the woods. Jade took Diego and Wendy there to meet her human friend Inez and a bunch of students from Mystic Falls High. However, it turns out that it was a freak party, so the trio of supernaturals turn around and start to leave, when a football jock insults them and throws a football at Diego's back. Enraged, Diego attacks the jock and rips his arm off. The blood splatters on Jade, causing her to go into ripper mode. Wendy panics during the chaos and when trying to prevent another townie calling for help accidentally incinerates her with her magic.. By the time the dust settles, all the human students in the area are dead. Wendy incinerates all the bodies in order to hide the evidence, but misses a key piece of it that leads Alaric to them. Jade is initially horrified at what she has done before suppressing all those emotions and becoming cold and unfeeling.
- Meanwhile Scene: The whole episode is one compared to the previous one, which takes place simultaneously but in the normal world.
- My God, What Have I Done?: Alaric when he realizes how he ignored the signs of Jade and the rest in trouble and sent them to a prison world when they needed help and understanding.
- Nice Job Breaking It, Hero:
- Kai had been trapped in his eternal hell with no escape...until all those students Alaric sent to the prison world freed him out of nothing but boredom and allowed him to run around loose.
- Jade, Diego, and Wendy weren't bad kids, just a bit misguided who lost their cool in the massacre. Sending them to a hellish prison has warped each into true monsters which Alaric recognizes.
- The only reason Kai was able to escape the prison world is because Josie decided to tell him all about Malivore.
- Resurrective Immortality: No one banished to the prison world dies for long, coming back to life after a few hours. This doesn't apply to the Saltzmans, however, since they aren't magically bound to this place.
- The Reveal: Alaric and Emma banished three students to the prison world after they slaughtered a group of humans in the woods. It also turns out that Alaric didn't have the whole story and the slaughter was largely an accident, but Alaric was too focused on his daughters to see that the students were troubled.
- Sadistic Choice: Kai gives one to Josie as payback for tricking him: she can either stay trapped in the prison world forever, along with her sister and father, or she can break the Mora Miserium and use her newfound power to open a way out, but she will become a monster in the process, just like her uncle. Even worse, Kai leaves her no time to make a decision, as he's about to jump into Malivore, which means Josie will forget this entire conversation. She makes the latter choice.
- Title Drop: Spoken by Wendy when she learns that Kai abandoned them and plans to leave the prison world by himself. Echoed by Kai when he learns that Josie tricked him and didn't give him the right spell ingredient.
- Unwitting Instigator of Doom: 10 years ago, Josie freed Jade, Diego, and Wendy from detention so they'd like her, which resulted in a massacre in the woods.
