Following on from realizing that Alaric is in the armory below the Salvatore Boarding House, Diego and Wendy go to investigate. Diego finds Alaric's jacket on the floor and, despite a warning from Wendy, he picks up the jacket to find his arm stuck in a bear trap. He becomes increasingly angry and Alaric warns him to calm down before ultimately stabbing him, temporarily killing him. Wendy creates a wall of fire between her and Alaric to protect herself and runs back upstairs, however Alaric is able to catch her when she trips. He is thrown across the room by Jade
, however, who wishes to feed on him and a fight ensues between the two. Jade stops fighting all of a sudden, however and apologizes for everything before passing out; a direct effect of Josie's magic. When Alaric questions what Josie did, she replies that she fixed her.
Hope dreams about walking into the hall of the Salvatore School, where she is met by children who chant "a new hero rises, and he will take flight but when the arrow finds him, a new hero dies" continuously. She tells the children to be quiet and they disappear, revealing Landon lying on the ground with a stab wound to the stomach. When she awakens at Alaric's desk trying to piece together the ascendant, she goes to check on Landon. She finds he is making a thought board, attempting to find out how he levitated the previous night. It is revealed that he attempted to fly by jumping off the garage roof, however he hurt his wrist in the process.
Someone knocks at the door of the Salvatore School and when Dorian answers, it is revealed to be Kai. He pretends to be someone called Joshua, and tells Dorian that Alaric promised him asylum at the school should he ever be in town. Dorian questions how he knows Alaric, and Kai reveals that he was at his wedding and brought quite the gift. When Dorian tells him that Alaric is not home and to call back another time, Kai reveals that he is aware that things have been hectic at the school and Dorian may have forgotten to take his vervain. With this, Kai compels him to find someone who can invite him into the school.
Alaric rushes Lizzie to the hospital given she has suffered a gash across her stomach in the car crash she and Sebastian experienced. Josie reveals that the dark magic is making her worse and she will not make it. Alaric begs Josie to do something and she reveals that she can, but will be unconscious for a while. With this, Josie siphons some of the magic from Lizzie and collapses. Jade arrives shortly after, revealing that Josie helped turn her humanity back on, and was training as an EMT prior to being trapped in the Prison World; she tells Alaric that he must do as she says, however as she cannot be near the blood.
Landon brings Hope tea as she is trying to figure out how to repair the ascendant. Hope reveals that the ascendant is spelled and therefore every time she tries to repair it, it breaks again. Dorian enters shortly after with Kai — who he introduces as Joshua — revealing that he is an expert in Prison Worlds. Kai tells the group that they have the wrong ascendant, and taking a look, he reveals there is a linking spell on the ascendant. He tells Hope that Alyssa sent the Saltzmans to a dangerous Prison World and that she will need his help to rescue them.
Jed, Kaleb and MG are searching for the perpetrator that stole from the armory. Jed and Kaleb get into a heated argument and MG believes this to be a manifestation of the previous rivalries between vampires and werewolves. It is eventually revealed that Jed is acting up because MG had a date with Alyssa, and MG tries to convince him that he doesn't care about Alyssa. Nevertheless, Jed is angry that Alyssa only talks about MG, and it is revealed that both Jed and Kaleb are into Alyssa. They eventually see the zombie from previously and begin following it.
Hope reveals that the only way to know if the Saltzmans are still alive, is to astral project there. Landon tells her that it is a bad idea, as she may get lost and not find her way back; despite this, Hope tells her that she must try. Dorian tells Hope and Landon that "Joshua" did research and has found a rare flower extract that forces people to tell their deepest secrets and, giving it to Alyssa, will force her to reveal the location of the ascendant. Landon leaves to find the flower with Dorian whilst Hope prepares to astral project.
Back at the hospital, Alaric is performing emergency surgery on Lizzie, guided by Jade. Jade points him to a "Laughlin Clamp" on the tray, and Alaric remarks that Lizzie's mother invented it. He is able to stabilize Lizzie, and Alaric thanks Jade. Josie awakens shortly after, and Jade questions what happened, Josie reveals that she can't remember and someone is missing from her memory. With this, Jade hands Josie the letter from Kai, and upon reading it, she realizes that the person missing must've been consumed by Malivore. Josie casts a spell that puts the three of them into a sleep-like state.
Kai, meanwhile, uses the crystal — the same one Josie and Lizzie had used previously — to contact the Necromancer. The Necromancer warns that he underestimates Hope, however Kai tells him that he has a plan. Kai questions if the Necromancer still has the golden arrow and, if given time, he will soon have Josie and all of the magic. Meanwhile, Dorian knocks Landon out instead of taking him to the falls to search for the flower.
Kai visits Alyssa in her cell, telling her that he is a big fan of hers, and questioning how she feels about teaming up with her.
At the Salvatore Boarding House, Alaric awakens and questions where Lizzie is. Josie reveals she is sleeping, and further reveals that the Prison World is made of magic, and therefore can be siphoned. Jade, Wendy and Diego arrive and reveal that they're all civil, just wanting to return home. Josie, however reveals that she cannot take everyone and someone must remain behind in the Prison World to be the anchor; she suggests Diego, however Alaric dismisses her and tells her they're not leaving anyone behind. Josie's dark magic takes over and she reveals someone is coming. Hope arrives shortly after in astral form, however only Josie can see her. Alaric tells her to warn Hope about Kai, but Hope reveals that Kai is already at the school pretending to be someone else. Alaric tells Hope that Kai is dangerous and should be led away from the school as soon as possible, and Josie reveals that they must leave the Prison World as soon as possible. Alaric tells Josie that he will remain behind so the others can return home.
When Hope returns to the physical plane, Kai is waiting for her. He asks how it went, but Hope tells him that she couldn't reach them. Kai finds the ascendant hidden within one of Alyssa's teddy bears, and tells Hope that all she needs is something equal to the power of a celestial event. Hope reveals she knows something, but they must go off-campus to find it. Hope brings them Hope tells Kai to look for a box with the Salvatore logo on and whilst he is looking, she attempts to stake him, but he is able to block her with magic. A fight ensues, but Hope realizes that Kai is distracting her. Kai reveals that Alyssa is casting a spell to cut the ties between Kai and the Prison World, which means the Prison World will implode. Kai reveals that he compelled Landon to walk into the path of a golden arrow, and that they will see if the prophecy is true. Kai tells her that she can't save them both and must make a choice between the Saltzmans and Landon.
Jed, Kaleb and MG are able to track down the zombie, and in an abandoned trailer, MG finds Rafael tied up.
In the Prison World, Josie reveals how the spell to siphon the magic from the Prison World works. She expresses the fact that when the spell begins, she cannot stop until it is complete therefore they must leave when the doorways open. Lizzie begs Alaric not to remain behind, given Sebastian will come for him, however he promises that he will be fine and they can find a way to bring him back later. Sebastian awakens shortly after.
Dorian is dragging Landon through the Woods, and it is revealed that he has been compelled. Landon asks what he has been compelled to do, and Dorian reveals that he has been compelled to hold him while he is shot with the golden arrow.
Alyssa is performing the spell when Hope rushes in to stop her, revealing that if she performs the spell, she'll kill everyone inside. Alyssa tells Hope that Kai didn't mention that, and Hope tries to explain to her that she doesn't want to be responsible for someone's death, and Alyssa stops the spell. The ascendant begins spinning, however and Alyssa is startled, but promises that she isn't the one performing the spell. Wendy and Jade return to the real world, but Diego has other intentions and attacks Alaric, citing that he will never forgive him. Sebastian intervenes, however, and snaps Diego's neck. Sebastian tells Alaric to take care of Lizzie, and uses his vamp speed to force Alaric to go through the portal back to the real world. Sebastian asks how the deal goes down, and Josie tells him that when he touches her, he will become the anchor. Sebastian asks Josie to tell Lizzie "something a better man would say", and with this, he becomes the anchor and Josie returns to the real world, free from the dark magic.
Dorian is holding Landon whilst the hooded figure aims the arrow. Dorian is able to break the compulsion, however, and when the hooded figure sends the arrow, Dorian turns his back and is shot with the arrow instead. Landon tells Dorian he will get help, however Dorian tells him that he won't make it. Believing himself to be close to death, Dorian tells Landon it isn't his fault, but to always be a hero.
Josie and Hope arrive at the clearing and Josie questions what happened. Hope tells her that she had to make a choice, and she didn't choose Landon, but it will be alright because he will be fine. He emerges later flying through the sky with flaming, phoenix wings. Hope is startled and Landon is revealed that he has finally figured out how to fly.
It is revealed that Jade, Wendy and Alyssa have been confined to the Old Mill via a boundary spell. Jade tells Josie that Lizzie should rest for a day or two, and tells Josie that she is glad to have the real Josie back.
In the Prison World, Sebastian drinks alone, and it appears that the world is unstable. Lizzie astral projects to see Sebastian, and she reveals that the world will not last much longer. Lizzie tells Sebastian to jump into the Malivore pit in Fort Valley, however Sebastian fears he won't make it in time. Sebastian apologizes to Lizzie, but sarcastically tells her that he warned her to stay away when they first met. With this, Lizzie's astral projection fails, and Sebastian remarks that he would've liked the Prison World.
Back at the school, Rafael reveals that the last thing he remembers is being abducted and locked in the trailer. Kaleb asks about Dorian, and Alaric reveals that he is in the hospital. They all share a drink and wish for tomorrow to be a better day.
Hope and Landon lie together, and Hope apologizes for not choosing Landon. Nevertheless, Landon tells her that the decision to save six lives over one was the right choice, and he isn't sure he would've been able to make the same decision. Hope remarks sarcastically that she can't fly, though, and asks Landon what it is like; he promises to take her for a flight someday, but she is already asleep.
Lizzie witnesses the ascendant break, and is visibly upset, and she and Josie embrace. Kai is still tied up as a result of Hope's magic, but is able to use the crystal from before to summon the Necromancer. He asks for someone to free him, however the Necromancer refuses, citing that he knows Kai betrayed him. Alaric arrives shortly after, decapitating Kai and killing him for good.