The always unwelcome Vulture pops back into Jake and Amy’s lives, threatening to swoop in and take something important away from them. Meanwhile, Boyle and Rosa must track down “Sergeant Peanut Butter,” the kidnapped NYPD horse that Charles envies, and Holt challenges Terry to be less image-conscious.

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Season 05, Episode 01 – “The Big House Pt.1”
In the Season 5 premiere, Jake and Rosa assimilate to their new lives behind bars, but both cope in very different ways. Jake bonds with his cellmate and is forced to join a prison gang led by a notorious inmate. 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.

Season 05, Episode 02 – “The Big House Pt.2”
When the warden asks Jake to investigate Romero’s drug smuggling operation, Jake and Caleb find themselves caught between the loyalty Jake has sworn to both of them. Meanwhile, Amy is offered a deal by a local mobster who claims he can prove that Hawkins is guilty, but Holt and the rest of the gang think they have a safer plan.

Season 05, Episode 03 – “Kicks”
Now that he’s officially back at the precinct and desperate to solve a real case, Jake finds a loophole to get out of his temporarily designated desk duty. Unfortunately, that loophole rests on his ability to pass an official evaluation performed by Holt. While Charles provides Jake with moral support, Terry and Amy help Rosa, who believes Pimento may be cheating on her.

Season 05, Episode 04 – “HalloVeen”
The Nine-Nine embarks on its fifth annual Halloween Heist and, as usual, everybody has a plan and no one is safe. Relationships and friendships are tested as the title “Amazing Human Slash Genius” must be snagged by midnight, leaving everyone pitted against each other.

Season 05, Episode 05 – “Bad Beat”
To track down the infamous arms dealer Dan “Daniel” Valdano, Jake and Terry go undercover at an illegal gambling club, but when Holt gets involved to coach the two in the art of poker, his addiction resurfaces. Meanwhile, Boyle buys a food truck that was formerly used in a brutal string of murders without telling his investor, Amy, and Hitchcock and Scully challenge Rosa to a “Butt-lympics”.

Season 05, Episode 06 – “The Venue”
The always unwelcome Vulture pops back into Jake and Amy’s lives, threatening to swoop in and take something important away from them. Meanwhile, Boyle and Rosa must track down “Sergeant Peanut Butter,” the kidnapped NYPD horse that Charles envies, and Holt challenges Terry to be less image-conscious.

Season 05, Episode 07 – “Two Turkeys”
Jake and Amy attempt to get their parents to bond over Thanksgiving dinner, but their first holiday together as a family does not go well. Meanwhile, at the precinct, Holt and Kevin’s special Thanksgiving pie is stolen from his office and Holt searches through the ranks for the possible culprit.

Season 05, Episode 08 – “Return to Skyfire”
When Terry’s favorite author, DC Parlov, returns to the precinct because his latest manuscript was stolen, Terry and Jake convince Rosa to go undercover with them at a fantasy fiction convention to find the culprit. As drama ensues between Parlov and another writer, Terry admits that he’s been writing a book of his own. Back at the precinct, Holt, Amy and Charles take a forensics course, but Charles’ big mouth gets him in trouble.

Season 05, Episode 09 – “99”
While the entire precinct attends a funeral in L.A., Holt learns that he is in the running to become Chief Commissioner of the NYPD. But after missing their flight back home, Jake must devise a variety of ways to get Holt back in time for the interview. Forced to stay with some estranged members of the Boyle family, Amy tries to convince everyone that she can be laid-back; Terry panics about losing his first-class flight; and Charles uncovers some new information about Rosa’s personal life.

Season 05, Episode 10 – “Game Night”
In the Season 5 fall finale, Rosa begs Jake to help her break some big news to her parents, but her plan is thrown off when they wrongly assume the two are dating.

Season 05, Episode 12 – “Safe House”
After Seamus threatens Kevin, Holt devises an elaborate plan to hide him in a safe house, with Jake as his guard. Kevin is miserable as the 99 works overtime to find Seamus and take him down.

Season 05, Episode 13 – “The Negotiation”
Jake is called upon to negotiate a hostage situation with a jewel thief, only to discover that the culprit seems to be a familiar face. Amy and Gina help Charles with the high demands of his new food truck, and Holt panics when a member of the Police Commissioner selection committee decides to interview Hitchcock about Holt.

Season 05, Episode 14 – “The Box”
Jake embarks on an all-night long interrogation to elicit a confession out of a suspect. But when Captain Holt skips the opera in order to stay back and help, the two cops clash over how to get him to talk.

Season 05, Episode 16 – “NutriBoom”
Jake and Charles realize that they’ve been suckered into the cult-like NutriBoom pyramid scheme, and must find a way to sever their contracts.

Season 05, Episode 17 – “DFW”
Then, Jake invites his newly discovered half-sister to stay with him in New York, but when he and Amy realize she’s a bit of a nightmare, they must find a way to get her back home to Dallas.

Season 05, Episode 18 – “Gray Star Mutual”
When a fire destroys Charles’ food truck, Pimento shows up to the scene as the insurance agent. Meanwhile, Rosa helps Amy to see that it’s okay to get excited about picking her wedding dress, and Gina and Terry coach Holt in the art of social media.

Season 05, Episode 19 – “Bachelor/ette Party”
Charles plans an elaborate scavenger hunt for Jake’s bachelor party, but the day goes awry when the guys decide to take some short cuts instead. Meanwhile, Amy’s bachelorette party escalates when the ladies realize she previously slept with a member of her soon-to-be wedding band.

Season 05, Episode 20 – “Show Me Going”
When Rosa responds to an active shooter alert, the rest of the squad is forced to stay back, desperately fearing for her safety. Feeling helpless, Jake frantically brainstorms ways to offer his assistance, Terry faces an existential crisis and Gina and Amy try to make themselves useful by fixing Rosa’s broken toilet.

Season 05, Episode 21 – “White Whale”
Rosa and Amy team up to take down their “white whale” suspect—a ruthless killer who has managed to elude them for seven years—while Terry helps Jake tackle his wedding planning chores. Then, Captain Holt and his rival, Olivia Crawford, try to convince each other to step down in the campaign for commissioner.

Season 05, Episode 22 – “Jake & Amy (”
In the Season 5 finale, Jake and Amy’s wedding day is threatened, and Charles and the whole squad rush to help save it. Amidst the chaos, Holt hesitates to open the email that will indicate if he has won his campaign for commissioner, despite Gina’s encouragement. Meanwhile, Terry gently pushes Rosa towards a potential love interest.

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