Season synopsis
Contains spoilers for this season and earlier seasons.
Jake and Rosa enter season five behind bars after Lieutenant Hawkins frames them, and they have to learn different ways to survive prison. Holt finds proof against Hawkins, but getting the detectives released comes with a cost: he owes mobster Seamus Murphy a favor. Once they return to the Nine-Nine, Jake struggles to resume field work, while Rosa ends her relationship with Adrian Pimento. She also tells her family that she is bisexual, a vulnerable conversation that the squad backs her through.
Outside the precinct, Gina returns from maternity leave, Charles tries running a food truck, and Amy passes the sergeant's exam. Jake and Amy's relationship moves toward marriage when he proposes during their latest Halloween heist and she says yes. Holt, meanwhile, learns he is being considered for NYPD commissioner. The squad helps him manage Murphy's demands without letting the captain knowingly break his moral code, but Murphy uncovers the scheme and threatens Kevin.
Jake stays with Kevin in a safe house while the Nine-Nine tracks Murphy's operation. Kevin ultimately helps bring the mobster down, freeing the squad from Holt's dangerous bargain. Amy and Jake's wedding plans then collapse when a bomb threat forces everyone away from the venue. They still marry outdoors beside the precinct, with their friends gathered around them. At the reception, Holt receives the commissioner decision, but his unreadable expression leaves the result uncertain.