When a series of events leads Josie (Kaylee Bryant), Lizzie (Jenny Boyd) and Alaric (Matthew Davis) to the prison world, they come face to face with the twins’ evil uncle Kai (guest star Chris Wood).

Hope (Danielle Rose Russell) finds herself in a race against the clock as the threat of the prophecy looms and the pressure to rescue the Saltzmans grows. Meanwhile, Alaric’s (Matthew Davis) attempt to keep his family safe leads him to make a difficult decision. Aria Shahghasemi, Kaylee Bryant, Jenny Boyd, Peyton Alex Smith, Quincy Fouse and Chris Lee also star.

Emma suggests the students participate in the group simulation, and Hope, Josie, Lizzie, and MG learn they must confront their conflicts head-on or face the consequences.

When things take a dark turn on the twins’ 17th birthday, Lizzie (Jenny Boyd) is left to make a difficult decision. Meanwhile, Hope (Danielle Rose Russell) takes drastic measures when she and Alaric (Matthew Davis) clash over how to handle an issue involving Josie (Kaylee Bryant). Finally, Rafael (Peyton Alex Smith) makes a heartbreaking discovery.

In a race to save Josie (Kaylee Bryant), Hope (Danielle Rose Russell) infiltrates her subconscious and finds herself in a fairytale world filled with dark magic. Back at the Salvatore School, Alaric (Matthew Davis), Lizzie (Jenny Boyd) and the Super Squad commit to their own risky plan to get Josie back despite the potential consequences. Aria Shahghasemi, Quincy Fouse, Peyton Alex Smith and Chris Lee also star.

In order to get a handle on some urgencies at the school, Alaric (Matthew Davis) sends the students off-campus for their first-ever field day. But when a medieval monster arrives with a challenge, the students are left scrambling to guess which one of them may be a worthy opponent. Danielle Rose Russell, Aria Shahghasemi, Kaylee Bryant, Jenny Boyd, Quincy Fouse, Peyton Alex Smith, Chris Lee and Ben Levin also star.

The Super Squad pull out all the stops when they learn some devastating news involving one of their own. Alaric (Matthew Davis) turns to Sheriff Mac (Bianca Kajlich) for help getting some timely affairs in order. Danielle Rose Russell, Aria Shahghasemi, Jenny Boyd, Quincy Fouse, Peyton Alex Smith, Chris Lee and Ben Levin also star.

The Super Squad pull out all the stops when they learn some devastating news involving one of their own. Alaric (Matthew Davis) turns to Sheriff Mac (Bianca Kajlich) for help getting some timely affairs in order. Danielle Rose Russell, Aria Shahghasemi, Jenny Boyd, Quincy Fouse, Peyton Alex Smith, Chris Lee and Ben Levin also star.

The students prepare to put on a musical about the founding of the Salvatore School at the behest of their mysterious new guidance counselor. Meanwhile, as Landon (Aria Shahghasemi) throws himself into writing the musical and Lizzie (Jenny Boyd), Josie (Kaylee Bryant), Kaleb (Chris Lee) and Jed (Ben Levin) dive into their roles, Hope (Danielle Rose Russell) distances herself from the musical.

After one of their own goes missing, Alaric (Matthew Davis) suggests Hope (Danielle Rose Russell) turn to the therapy box, which thrusts her into a twisted game set in a summer camp slasher flick. Meanwhile, Lizzie’s (Jenny Boyd) attempt to spend some time with MG (Quincy Fouse) doesn’t go quite as planned, and Josie (Kaylee Bryant) makes a big decision about her future. Aria Shahghasemi, Chris Lee, Leo Howard and Ben Levin also star.

After a sudden mass exodus of the school’s student body, Alaric (Matthew Davis) and the squad desperately try to recruit new students to keep the school afloat. Hope (Danielle Rose Russell) agrees to help Lizzie (Jenny Boyd) with the new student orientation. Josie (Kaylee Bryant) enjoys a fresh start on her first day at Mystic Falls High, while MG (Quincy Fouse) begins his semester of “no.” Chris Lee, Leo Howard and Ben Levin also star.