Kevin is sleeping when he hears Crowley talking to him. Crowley says that he knows Kevin is working with the Winchesters and advises him to give up. Kevin looks around but Crowley is nowhere to be seen on the boat, and Crowley says that he's in his head. The demon warns Kevin that he lost a finger the last time the crossed paths, and Kevin hallucinates every bone in his body breaking.
Later, Sam and Dean arrive in response to Kevin's call. He lets them in, wielding a frying pan, and tells them that he's been hearing Crowley in his head. The brothers assure him that if Crowley knew where he was then he'd already be there, and Kevin explains that he deciphered the second trial. Kevin tells them that to pass the second trial, someone must go to Hell, rescue an innocent soul, and take it to Heaven. Dean figures that they need an expert and the brothers go to a crossroads and cast the ritual. A demon appears and, upon seeing them, immediately tries to leave... only to discover that they've drawn a devil's trap around the road.
The brothers take the crossroads demon to a safehouse and torture him with holy water. They demand that they tell him how to enter Hell uninvited, and the demon says that it's forbidden. Unimpressed, Sam pours more holy water on him and the demon finally tells them for a price, a rogue Reaper will smuggle someone into anywhere, including Hell. Once he's spoken, the demon begs them to kill him rather than let Crowley find him. Dean agrees... once the demon tells them everything.
Sam and Dean drive to a club and talk to the taxi driver outside. They know his name, Ajay, and tell him that they know what he does. Ajay points out that they're flesh and blood, and says that no one wants to go to Hell. He agrees to take them, but only agrees if they will promise him a future favor. When they wonder how he knows them, Ajay explains that he was the Reaper who took Bobby to Hell. They don't believe him but Ajay says that Bobby was on Crowley's black list. Dean asks for two tickets there and three back, and Sam draws him off to the side. When Dean points out that Sam hasn't been on top of his game and they need to get Bobby back, Sam assures him that he'll find Bobby and rescue him. The brothers go back to Ajay, who explains that Sam will be back in exactly 24 hours. He tells Dean to be back then and then leads Sam off into an alleyway... while nearby, a homeless man watches the entire encounter.
Ajay leads Sam into a dead-end alley and tells him to take his hand. The ground shakes and the graffiti opens up to reveal a glowing portal that sucks them back in. They're transported to Purgatory and Ajay explains that Sam has to go on to a portal, a back door to Hell. Ajay refuses to go, pointing out that smuggling a Winchester into Hell is a major danger to him, and tells Sam that he'll be back to get him in 24 hours. As Sam takes out the demon-killing knife, Ajay tells him that it's a good thing that he brought it because Purgatory isn't an easy place, and then disappears.
Dean returns to the ship with food and Kevin emerges from hiding. Kevin wants to move out before Crowley arrives, but Dean tells him to chill out and offers him a burger. Once the teenager reluctantly emerges to take the food, Dean tells him that it won't ever end because people like them have to carry some extra weight. Kevin says that he can't take it but Dean tells him that he can do it, and all he can do is suck it up and push through. After thinking about it, Kevin takes Dean's pie and goes to his room.
Ajay returns to Earth and gets into his taxi, and Crowley is waiting in the back seat. The demon locks the doors and asks Ajay if he has anything to report. When Ajay says that he doesn't, Crowley points out that one of his operatives saw Ajay leave with Sam. Ajay admits that he moonlights as a freelancer, but Crowley tells him that he doesn't freelance with the Winchesters. The Reaper explains that he took Sam to Hell and reluctantly tells Crowley when Sam is coming back. Once he's satisfied he knows everything Ajay can tell him, Crowley kills the Reaper with a demonic blade.
Sam makes his way through Purgatory and a creature attacks him. They fight and Sam decapitates it with its own weapon, and then continues on. He finally comes to the portal and finds it blocked, and pries the rock away. When Sam enters it, he finds himself in a dark hallway in the bowels of Hell. After marking the portal with his wristwatch, Sam enters the labyrinth. Tortured souls cry to him, begging for him to release them. One woman says that she's been praying forever for Sam to come.
Continuing on, Sam enters a cell and finds a man standing against the wall. He turns and Sam realizes that it's Bobby... and Bobby punches him. He tells Sam to get out, figuring that it's a demon in disguise. Sam tries to prove he is who he claims and tells him some personal things that nobody else would know. They hug and Bobby explains that the demons keep sending Sams and Deans with black eyes to torment him. Sam explains that he's there to rescue him and gives Bobby the demon-killing knife.
Crowley calls in his new assistant demon and tells her to find out what's going on. He orders her to find Kevin and the half-tablet that he has.
Dean makes breakfast for Kevin and calls him out. Kevin finally comes in from outside and made a preemptive move: he hid the tablet temporarily. He refuses to tell Dean where he hid it, and then goes into his demon-warded closet. Naomi appears in the room and introduces herself to Dean. Dean knows about what she did to Castiel, and Naomi points out that she rescued Castiel from Purgatory. Unimpressed, Dean notes that she brainwashed Castiel but Naomi says that all she's been doing is trying to keep Castiel stable. The angel admits that she told Castiel to get the angel tablet at any cost, but she was just doing her job. Dean doesn't trust any angel, but Naomi points out that he didn't ward the ship against angels. She wants them to work together to seal Hell, and then tells Dean that Ajay took Sam through Purgatory to get to Hell.
Sam leads Bobby back to the portal but they're forced to hide when a demon comes by. Sam attacks it and Bobby uses the knife to kill it. Another demon attacks and Bobby kills it, but a third demon appears disguised as Sam. Forced to choose, Bobby finally kills one Sam, and fortunately gets the right one.
Dean goes back to the taxi and discovers Ajay's corpse in the taxi.
Sam and Bobby go through the portal back into Purgatory. Bobby is less than thrilled to discover where he is.
Dean calls Benny and asks how he's been. Benny says that he's been getting by and is glad to hear from Dean, and Dean asks him for a big favor.
As Sam leads Bobby to the earth portal, he explains what is happening. Bobby says that he'd be glad to help, but Sam points out that they burned Bobby's bones and that he has to go to Heaven to complete the trial. When he hears the news, Bobby says that he figured that once he dead, that'd be an end. He agrees to head to Heaven, but tells Sam to get him out if they figure out a way to bring him back. Sam reaches the spot and realizes that it's the proper time, but there's no sign of Ajay... and they have no way out.
The next morning, Benny meets Dean, who explains what's going on. He asks Benny to go back, and Benny points out that Dean would have to behead him to send him there. When Dean admits that he hasn't been there for his friend, Benny immediately agrees to do it. Touched, Dean says that he owes him and Benny says that he wants a break from Earth. He doesn't belong with vampires or humans, and it's starting to wear on him. Dean promises to fix it when he gets back, and tells him to ride back with Sam. Benny tells him to get on with it and Dean takes out a knife. First he shakes Benny's hand and hugs him. He then steps back and decapitates his friend.
As they wait, Bobby wonders what Sam went through to try and rescue Dean. He quickly works out that Sam didn't try to rescue Dean despite their agreement. Before they can pursue the matter, more monsters attack them. As they struggle, Benny arrives and helps them, ripping out their attackers' throats. Sam stops Bobby from killing Benny, who explains that Dean sent him. Bobby doesn't believe it and figures that the brothers really lost it while he was gone.
Dean drives away and Crowley's homeless demon takes note.
As they walk back to the portal he used before, Benny explains that he's a disgrace to his own people. They prepare to go through, and Bobby tells Sam that he figures that he'll see him again someday. They cut their arms and recite the ritual to let Bobby enter Sam's blood. Sam turns to Benny and says that it's his turn, but three vampires arrive. Benny tells Sam that they want him and asks him to tell Dean he said goodbye. Before he goes, Sam tosses him the weapon he took earlier. As Benny fights the vampires, Sam turns back and sees them tearing the vampire apart.
That night, Dean drives to Maine to the spot where he appeared before. Sam comes through and the brothers embrace, and Sam explains that Benny chose to sacrifice himself to save them. When Sam says that Benny probably wouldn't have come back anyway, Dean admits that he's probably right and says that it's time to put Bobby where he belongs. Sam cuts open his arm and recites the ritual, and Bobby's soul floats up... and stops. Crowley appears and says that Hell is too good for Bobby.
When the Winchesters come at him, Crowley easily casts them back and prepares to destroy Bobby. However, Naomi appears and stops him. Crowley warns that the Winchesters will lock them both away, but Naomi figures that she'll let them seal Hell and deal with the rest later. Crowley insults her and teleports away, and Naomi sends Bobby's soul on to Heaven. She tells Dean that she can trust him and teleports away, and Sam recites the last part of the trial. He clutches at his hand in pain as it glows, and the pain slowly fades away.
Back at the ship, Kevin is putting up angel wards on the windows when he hears Crowley in his head, taunting him. The ship starts to vibrate and the windows shatter, and Crowley teleports into the room. He explains that he found Kevin's mother and tortured her. When she didn't give the location, they killed her and got the address from her smartphone. Crowley dismisses mortal as nothing compared to him and begins torturing Kevin.
As they drive back, Dean explains that he didn't burn Benny's bones in the hopes he can find a way back. Sam admits that Benny was different from what he thought and says that Dean should leave the vampire a choice. They get to the ship and Kevin doesn't respond to their calls. When they turn on the lights, they discover that all of his notes are coming. Dean assumes that Kevin freaked and made a run for it... and they have no idea where.