Jake and Rosa assimilate to their new lives behind bars, but both are coping in very different ways. Jake bonds with his cellmate, Caleb, and is forced to join a prison gang led by notorious inmate Romero, in order to gain his protection. Meanwhile, in the women's prison, Rosa puts Holt and Terry to the test by having them complete outrageous favors for her. Back in the precinct, Amy and Charles are doing all they can to exonerate their colleagues.
|Andy Samberg||...||Jake Peralta|
|Stephanie Beatriz||...||Rosa Diaz|
|Terry Crews||...||Terry Jeffords|
|Melissa Fumero||...||Amy Santiago|
|Joe Lo Truglio||...||Charles Boyle|
|Chelsea Peretti||...||Gina Linetti (credit only)|
|Andre Braugher||...||Captain Ray Holt|
|Dirk Blocker||...||Michael Hitchcock|
|Joel McKinnon Miller||...||Norm Scully|
|Lou Diamond Phillips||...||Jeff Romero|
|Toby Huss||...||Warden Granville|
|Sarah Chaney||...||Visitation Guard #2|
|Winston James Francis||...||Tank|
|Chiquita Fuller||...||Visitation Guard #1|
|Matt Leonard||...||Alan Wilson|
|Faruq Tauheed||...||Gang Leader|
- Gina Linetti is absent from this episode, but mentioned in Boyle's dream (but not outside of it) to be on maternity leave.
- The woman that Hitchcock is seen visiting at the woman's prison is played by Danielle Aubuchon who is the real life wife of Dirk Blocker.
- Jake has grown a beard, despite previously stating that he cannot grow facial hair.