"Maximum Security" is the 21st episode of Season Three of the FOX television show Brooklyn Nine-Nine. It is originally aired on April 5, 2016 to 2.71 million viewers.
In an attempt to get information on a criminal operation, Amy has to go undercover at a women’s prison and befriend one of the prisoners. Meanwhile back at the precinct, Holt and the team plan a fake funeral in an attempt to catch a hitman.
Continuing from the last episode, the core group has decided to bring Jimmy "the Butcher" Figgis down after Pimento went into hiding. They only know two key factors; there's a hitman in the FBI with a scar on his right hand, and that Figgis has a sister, Maura, who is in a maximum security prison in Texas. They need someone to go undercover and befriend Maura, and while Amy volunteers, the group chooses Rosa since she's tougher.
Back in Holt's office, Holt discusses a way to lead the hitman to them. They'll fake an investigation to find "Pimento's" body, and hold a "funeral" for the deceased. Using Gina's suggestion, they use Hitchcock as a body double for Pimento, forge the coroners signature, and notarize it, making it look like a real investigation.
Meanwhile, Rosa is going over her undercover alias with Jake and Boyle. She will be "Isabelle Cortez" a pregnant inmate who is being transferred, while Jake and Boyle will pose as the prisons OBGYN doctors to brief with her when possible. They go down to the Texas and let Rosa into the prison, but when she gets inside, a convict she arrested long ago recognizes her immediately. With her cover blown, Jake turns to Amy and asks her to become "Isabelle".
Amy/"Isabelle" enters prison, and soon makes a name for herself as a supplier for objects from the outside (burner phones, drugs, porn etc.). This catches the attention of Maura, who threatens "Isabelle" if she doesn't stop. When "Isabelle" steps up to her, Jake pulls her into the doctor's room and warns her that she might be in danger and tells her to take it slow. Amy does keep a bit of a slow pace around Maura, but Jake keeps pulling her back into the doctors' office with ridiculous excuses.
Back in Brooklyn, the rest of the squad initiate the fake funeral for Pimento. Gina and Holt greet the mourners with high-fives (it was originally handshakes, but they needed to find the scarred person), but things go slow. They do find a suspect wearing black gloves and corner him but find out he's only a pickpocketer. With the funeral almost over, Rosa gives a eulogy saying that there's nothing that can bring back Pimento. Terry reminds her however that they will not stop until Figgis is arrested and then Pimento will come back.
Back in the prison, Amy intentionally pushes Maura out of the frustrating orders, and she and Jake argue about his orders. Jake admits that he isn't strong enough to be here and watch Amy undercover surrounded by violent inmates, and wanted her safe. It's decided that Jake will take himself off the case, and the couple stages a beat up in front of the inmates. As Jake heads back to Brooklyn, Boyle watches the camera feeds and sees Maura invite "Isabelle" into her team.
|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|
|Andre Braugher||...||Captain Ray Holt|
|Dirk Blocker||...||Michael Hitchcock|
|Joel McKinnon Miller||...||Norm Scully|
|Aida Turturro||...||Maura Figgis|
|Carrie Armstrong||...||Roena Luesto|
|Nicole J. Butler||...||Sylvia Dunnes|
|Josh Feinman||...||Mystery Guest|
|Paul Mabon||...||Officer Lou|
|Ken Narasaki||...||Li Ongoing|
- Amy Santiago goes undercover in this episode as a pregnant woman. In reality, Melissa Fumero was actually pregnant with her first child during filming.