J.R. finds himself in financial hot water and must broker an extension of his loan.

The trap door opens into the basement, which he equipped with a steel core door and titanium kick plate. The two are attacked by three vampires and one gets the drop on Bobby, but he is saved by Benny. Agent Adams is looking for Rufus. J.R.'s counter-revolution brings the oil wells back under private control, which reconciles him with the cartel. Lucy gets a modeling job, further upsetting Mitch. Bobby, how many value of big deal no.3? Bobby and Dean leave Sam in the room, and take the Impala to the address they have been given. He gives Sam beer laced with it when Sam is possessed and Ellen has to drink a holy water shot after she escapes the demon attack on the Roadhouse.

While they are tracking investigating the deaths they also encounter Rufus, who joins in the hunt. Bunny complied and asked Bobby to take care of her daughter if anything ever happened to her. She admits that she came from Purgatory. Bobby enters a deal that will get Ewing Oil back into the cartel, but for which he doesn't have the promised capital. He carries multiple cell phones around, presumably like Bobby's phones and gives advice like Bobby did, wears one of Bobby's old hats sometimes and uses some of Bobby's old phrases. When Sam disappears to work a case on his own, Bobby encourages Dean to trust him in spite of his continued mental lapses. EWen Crowley arrives, he tells his agreement with Dick to Dean and Sam and gives sample of his blood. Bobby is in favor of telling the truth, insisting that Sam will find out the truth eventually, and he deserves to hear the truth from them. Dean tries to comfort by saying that at least he got to see his wife again. Distressed, Bobby insists that the one thing they must do is keep this timeline intact. Crowley gives Dean Death's scythe in order to kill Death and also reveals that he gave Bobby back the use of his legs in their deal. In the aftermath of Castiel's transformation, Bobby, after a moment's pause, gets down on his knees to appease the angel, and orders the Winchesters to do the same.

Castiel stops them, and tells Bobby to stand, because they only fear him, and do not love him. Following the customary montage of the season, the episode opens with Crowley having just been summoned to Sucrocorp and imprisoned beneath a digital devil's trap. They find the remains of a deputy forest ranger, and call his supervisor, who then uses his radio to call back-up.

Crowley vanishes, and Castiel kills Raphael. He leaves, and when they later pray for his return, Bobby traps him in a circle of holy fire. Miss Ellie tells J.R. that she won't stand for any mudslinging and attends the hearing to see if he obeys. Dean, however, is less than certain. They go to the local museum, and research the house, while Bobby attempts to move a lamp. No information He kisses her on the cheek, and she smiles. Annie and Bobby watch a more experienced ghost, Haskel Crane, move a chair effortlessly at a bar, and decide to ask for pointers. Later, when Ellen suggests that the ship needs to be sunk, Bobby reveals her fate, and admits that he does not want to lose her. Bobby finds the brother squaring off with Dick, and they all start heading for the door. Miss Ellie's resentment of Ray's relationship with Jock grows.

When Sam and Dean try to go after Lilith without him, Bobby tells them "Family don't end with blood, boy  and more than once Dean tells Bobby he's like a father to him. On Earth, Sam casts a spell and releases Bobby's soul towards Heaven, but his soul is intercepted by Crowley who intends to take him back to Hell. Bobby makes sure that he will still have the use of his legs before releasing him from the Devil's trap. Dean comments that they've never actually seen the spell Bobby taught them work. The spell requires Sam to commit patricide...but he does not need to kill his blood father; a surrogate father will do. Bobby quotes the poet: "a man's reach should exceed his grasp." Two leviathans spot the ambulance, and start running toward it.

They are told that in order to move objects they must either achieve a Zen calm, or uncontrollable rage.

In the end, Bobby says, "As fate would have it, I adopted two boys and they grew up great. She gathers the family, including Gary and Val, to explain what it means. Bobby tries to look after Dean in the wake of Sam's death, but Dean pushes him away in anger. Bobby tells Sam and Dean about a string of supernatural activity along I80 which has culminated in murders in Sandusky, Ohio. Dean and Sam also burn Bobby's flask so his ghost can rest in peace. They leave the room and he performs a spell to return the spirits to rest. "Bobby" leads Sam to a house in the woods where he says what Sam needs to move on is before being killed by "Dean" who tries one last time to convince Sam to fight. Thanks to Benny sacrificing himself to hold off more vampires, Sam escapes to Earth with Bobby's soul. Lucifer works his way into Heaven. His neighbor Marcy Ward expresses an interest in him, but a messy incident with an okami ends any possibility of a relationship. With John held captive by the demons, the boys turn to Bobby for help. Bobby later puts Enochian sigils on the windows of his home to keep out Castiel, but there are some errors in the marks. In her distress she drops her wine glass and steps on the fragments, cutting her heel. When he learns that the okami might be after her, he breaks down her door with a shotgun, scaring her, but drawing out the okami, which had been waiting in her bedroom to kill her. The adult Bobby looks at the boy, and tells him that he'll bury the body in the salvage yard.

They find. He cannot reach it, but something moves the sword toward to him, allowing him to continue the fight and kill the creature. Quickly, he writes down a series of numbers that he knows he must get to the boys. Bobby finds that they are Egyptian, and associated with Osiris. Dean calls Chuck who tells Dean the confrontation between Michael and Lucifer will take place at Stull Cemetery near Lawrence in Kansas, where the boys first lived. Rufus tells him to seek out his worst memory, because if he faces it, he can wake up.

When Sam confesses that his killing Lilith freed Lucifer, Bobby coldly tells him that once the hunt is over, he wants nothing to do with Sam.

Miss Ellie discovers Jock is one of the backers of a development she's been campaigning to stop.

Dean informs Sam and Bobby about his deal with Death to return Sam's soul if Dean can wear his ring and perform his duties for a full twenty four hours. Sue Ellen toys with cheating with an old college beau named Clint Ogden. After Dean dies, seemingly for real, on the Wednesday, Sam becomes obsessed with finding the Trickster, while ruthlessly hunting other evil across the country. Bobby sends the brothers off to Frank Devereaux, who can make them new fake IDs.

While Bobby was interrogating the crossroads demon, Marcy Ward rang his doorbell with a homemade peach cobbler. Olivia also began to kill her family out of disgust towards them and their greed. Bobby angrily dismisses the idea, saying they had just talked Dean out of consenting to possession by Michael. Garth mentions the theory again to Sam at their motel room, and Sam admits that after Dean's beer disappeared shortly after Bobby's death, he too suspected that Bobby might be around. Bobby suggests that they find a away to get his flask inside the building so that he can look around, but the Winchesters decline. Bobby stays with Sam to work the phones and watch the younger Winchester while Dean goes to investigate a case. Dean manages to convinces Bobby he is only dreaming and he awakes. Inside his mind, Bobby has returned to the memory of Sam and Dean arguing over movies and snacks.

Meanwhile, Bobby has been getting flak from Dean, who feels like Bobby is being selfish because he doesn't have time to listen to his worries about Sam. As the most dangerous episode in the history of the Cold War, the Cuban missile crisis has inevitably attracted the attention of many diplomatic historians.

After killing the demon, Bobby answers phones and backs up other hunters posing as various law enforcement until Rufus knocks on his door. Bobby determines that it is made of human skin. He then takes the boys to meet an old friend, the psychic Pamela Barnes, who is blinded during a séance by Castiel. Omens lead Sam, Dean, Bobby and Castiel to Detroit, where Lucifer had always predicted Sam would say yes. He keeps seeing a child running through his memories. When he wakes, Bobby asks what the sigil was for, and Castiel reveals that it wards off angels. Sam later calls Bobby and asks him how he took control of his body when he was possessed by a demon in 5.01 Sympathy for the Devil. His research also suggests that Osiris can be made dormant if stabbed with a ram's horn. Bobby closes the kitchen doors. Bobby enters a deal that will get Ewing Oil back into the cartel, but for which he doesn't have the promised capital. As cremation is not undertaken in the Jewish tradition, Rufus is buried, in what is obviously a Jewish cemetery, rather than given a Hunter's Funeral Pyre. Bobby has extensive knowledge of the supernatural, and is well-known and generally well-regarded by other hunters such as Gordon Walker, Kubrick, Rufus Turner, Olivia Lowry, Isaac and Tamara among others. Bobby's mother is nervously putting food on the table, and his father looks angry. They find the place abandoned and rusting.

Bobby works with the boys and Bela Talbot to track down Jeremy Frost. Bobby tells Dean that he watched Sam save almost a dozen people back at the warehouse and he never let up for even a moment. He is hunting the Leviathan-made zombie in the woods with Sam and Dean, and realizes that this has already happened, and that something is terribly wrong. Olivia didn't see Bobby's mercy as a good thing due to being locked up and wanted revenge on him by killing Sam and Dean since Bobby was dead. The two hunters stalk each other through the house. The demon suggests that he knows a spell that will help, but he needs to make a deal for Bobby's soul to be able to work it. However, after becoming vengeful spirit temporarily, he asked Sam and Dean to put him to rest, which they did. After giving her location to the boys, they obtain Ruby's knife and prepare to leave to go after her.

Death comes to Bobby's town of Sioux Falls and raises the dead, including Karen, Bobby's dead wife. They give him a pen, and he scrawls the numbers on Sam's hand. After the boys leave for Ohio, he is test firing the Colt, when Ruby appears, and offers to help turn it back into a demon-killing weapon.

J.R. tries to take advantage of Sue Ellen leaving the Southern Cross to arrange the funeral to kidnap John Ross back but is foiled by Dusty. He wants to know Crowley's true name - the name he had as a human before he died and became a demon in hell - so he tortures the demon by using a blowtorch to singe its bones. Mitch's mother and sister, Afton, arrive in town for the wedding.

After finding the message from Bunny's lawyer on Bobby's old cellphone, Sam and Dean go to claim his inheritance and discover his history with Bunny and Olivia. Once Bobby has the information he needs, he burns the demon's bones, killing it and its host. Pan warns their mother not to trust Cliff. They argue, and when a cloud of demons appears Sam, Dean, and Bobby flee at Castiel's insistence.

Pam goes missing. According to Jo's Journal, Bobby frequented the Roadhousefrom around 1993. Ray proposes to Donna. Sam and Dean struggle to understand what exactly the Word of God mean. Bobby, Sam and Dean standing over Rufus' grave. J.R. starts a new plot to blackmail the Farlows into making Sue Ellen leave by buying up all the available crude oil to destroy their refinery. Sam and Dean make a plan to storm Dick's company building and kill him once and for all, with help from Castiel and Meg. Sam tries to prevent Dean from getting Death's ring, which was buried on Bobby's property, but Dean gets there first. He heals Dean and resurrects Bobby. Friends/Allies Bobby tortures a demon for information on Crowley's whereabouts, and cautions Sam and Dean that while Castiel has helped them in the past, they may be dealing with a "a Superman who's gone darkside."