Sheriff Jody Mills goes out on a blind date, unaware that it's actual Crowley. Jody is surprised at how readily they hit it off, and Crowley says that he can sense that she's had a great loss in her life. She breaks into tears, apologizes, and goes into the restroom to touch up her makeup. As she does, Crowley sets up a hex on the table and casts it, and Jody starts coughing up blood as she chokes to death. Dean calls to tell Crowley that they're giving in and will stop the trials as long as he stops killing the people they've saved. Crowley demands that they hand over the demon tablet as well, but Dean only agrees after the demon concedes to handing over the angel tablet that he has.
Later, Dean and Sam meet with Kevin, who digs up the tablet from where he's hidden it. Once they explain what they have planned, Kevin assures them that they're doing the right thing.
In Houston, Castiel and Metatron watch a bartender, Dwight Charles, as he sweeps up outside his bar. The two angels talk about God, and Metatron assures his friend that it was necessary that he kill the nephilim. He assures Castiel that the next trial won't involve killing anyone. Within the next 24 hours, Cupid is scheduled to visit Dwight and make sure that he falls in love with someone. Metatron needs the Cupid's bow to complete the second trial.
In Sioux Falls, Sam and Dean meet Crowley at a junkyard and prepare to make the exchange, tablet for tablet. Once they each prove that they have what the other wants, Crowley rolls out a contract to seal the arrangement. Sam offers to read it but Dean insists, saying that he'll take care of things.
Naomi receives a visit from one of her angels, Nathaniel. He tells her that a freelancer has found Castiel in Houston... and that Metatron is with him.
As Dean read the contract, Crowley can't resist taunting them, pointing out that they always lose because they're human and he's not. Dean steps forward to sign the contract... and handcuffs himself to Crowley. When Crowley tries to teleport away, he discovers that the handcuffs have devil's traps drawn on them. He punches Dean, who punches him back and says that he'll be glad to keep beating on the demon as long as it takes. The brothers tell Crowley that he's the third trial.
Castiel and Metatron go into the bar and order drinks. When Dwight comes over, Castiel tries to find out about his romantic interests without much success. Naomi and her angel squad teleport in and grab Metatron. When Dwight tries to interfere, an angel knocks hi out. Metatron tells Castiel to back down and then surrenders, and Naomi's angels teleport away with the Scribe.
The Winchesters take Crowley to consecrated ground: an abandoned church. They seal him within a devil's trap and manacle him, and then talk outside to review the purification ritual. Sam needs to inject Crowley with his purified blood once an hour for eight hours, and then feed him the rest. Dean reminds Sam that he'll have to purify his blood and lists off the many things that Sam has to confess about. Sam cuts him off and goes inside to the confessional booth. Meanwhile, Castiel teleports to the church and asks Dean to help him rescue Metatron, explaining that he's been trying to seal off Heaven while the Winchesters seal off Hell.
Naomi takes Metatron to her office and straps him into a chair. He reminds her that she was one of the archangels that tried to debrief him when God disappeared, forcing him to flee Heaven. As she prepares a skull saw, Naomi wonders why Metatron emerged from hiding after so long, but he merely quotes the Bible to her and she goes to work.
Castiel tells Dean what he's doing, and Sam over hears them. He tells Dean to go with Castiel and that he'll handle curing Crowley to complete the third trial. Dean reluctantly agrees, telling him to complete the ritual in eight hours whether he returns or not. Once Dean and Castiel leave, Sam goes inside and gives Castiel the first injection. Unimpressed, Crowley simply smiles smugly, while Sam's arms glow with the energy of the trials.
At the Letters base, Dean and Castiel meet with Kevin and give him the angel tablet. He refuses to translate, explaining that he is done being the Prophet now that he gave them the answer to the trials. Furious, Castiel slams against the wall and tells him that he'll be a Prophet until he dies, and that he has a duty. Kevin reluctantly goes to work while Dean and Castiel leave.
At the church, Sam gives Crowley the second injection. As he does, Crowley bites him on the arm. Shocked and disgusted, Sam goes to the Impala to get a bandage. As soon as he's gone, Crowley spits out the blood and uses it to cast a spell so that he can beg any demons that can hear him to come and help.
Dean and Castiel go to Dwight's bar and Dean enjoys free drinks from Dwight, who figures that Castiel saved his life earlier. Dean wonders if Castiel is sure that locking himself in Heaven with the other angels is a good idea, given what he did to them earlier, and Castiel admits that they'll probably kill him. A deliverywoman, Gail, comes in. She talks with Dwight, who introduces her to the other customer in the bar, Rod. She touches the two men and leaves, and Dwight and Rod abruptly fall in love. Dean and Castiel realize who Gail really is and go after her.
Crowley continues resisting the purification process and mocking Sam. He's interrupted when the church shakes and a crack in the floor breaks the devil's trap. Abaddon bursts in through the doors and tells Crowley that she's there to rescue him, and that she didn't need backup. Crowley is satisfied that a knight of Hell is there to help him, and Abaddon telekinetically tosses Sam out the window. However, when Crowley orders her to release him, she slaps him.
Dean and Castiel intercept Gail outside and Cupid demands that she give him her Bow. Dean stops him and says that they should talk things out first.
Abaddon beats Crowley and tells him that she doesn't care that Sam is trying to shut down Hell. When he tries to get to Sam's gun, Abaddon tosses it away and tells him that they're going to talk about a change in rulership. However, Sam comes back in and douses her with gasoline, and then sets her host body on fire. The demon essence leaves the body and flees outside.
Gail admits that she hasn't returned to Heaven since the civil war because everything there has been breaking down. Castiel assures her that he can fix things there and she willingly offers him the Bow tattooed on her hand.
Despite Naomi's torture, Metatron remains defiance. She asks what he's doing and he finally explains that he's angry with the angels for driving him from his home after God fled, after he sat at God's feet as the Scribe. Metatron assures her that they'll be payback for what they've done. When Naomi teleports out, Metatron sees the skull saw lying on the nearby table.
Crowley is surprised to discover that Sam is resealing the devil's trap, and point out that he delayed Abaddon long enough for Sam to defeat her. The demon starts quoting Girls and begging Sam for love, and Sam realizes that the cure is taking effect. Crowley says that he heard Sam confessing earlier and asks what he can do to get forgiveness. Sam holds up the syringe and says that it's the start, and Crowley willingly bares his neck.
As they leave the bar, Dean calls Kevin to see what he can find out about the angel trials. Naomi appears and assures Castiel that she's not there to fight. She explains that she's seen into Metatron's mind and knows that the trials are to gather the components for a spell. Metatron plans to use the spell to get revenge and cast all of the angels out of Heaven. She admits that the angels forgot their mission to protect Earth, the mission that God gave them. Naomi warns them that she also learned from Metatron that when Sam completes the third trial, he'll die. She begs Castiel to stop the trials and that they'll willingly take him back on peaceful terms. She teleports away and Dean asks Kevin if the angel was telling the truth. Castiel is sure that she was, but Dean tells him to take him back to Sam.
Sam prepares to feed Crowley his purified blood.
Castiel and Dean arrive outside the church, and the angel says that he's going to go fix Heaven. Once he teleports away, Dean runs in and yells at Sam to stop.
In Heaven, Castiel arrives in Naomi's office and discovers that Metatron has killed her with the skull saw. He puts the saw to Castiel's head and says that his friend should have listened to Naomi after all.
Dean tells his brother that Metatron lied and that the trials will kill Sam. Sam shrugs and admits that he's been expecting to die all along.
Metatron straps Castiel to the chair he previously occupied and then takes some of his essence. He heals the wound and explains that Castiel's essence is the last component of the spell he needs. The Scribe tells Castiel to have a good life as a human on Earth and, when he dies, he can tell Metatron his story. He then touches Castiel's forehead and teleports him away.
Sam insists that he has to finish the trials to save everyone that the demons will kill in the future, and admits that he confessed that he had sinned by letting Dean down in the past. He refuses to fail yet again when they're so close, but Dean insists that he needs Sam at his side to take on the demons. When Sam reminds Dean that he turned to a vampire, Dean insists that he needs Sam and that he has never put anything in front him. He begs Sam to see that, and Sam finally asks him how to stop. Dean tells him to let it go and binds his wound, assuring his brother that they'll figure it out. As they hug, the energy filling Sam fades away... and then he collapses in agony. Dean hauls him outside, saying everything will be fine, and calling to Castiel.
Castiel wakes up in the forest.
Kevin is preparing to leave when all of the scanners in the Letters base light up and alarms go off.
A storm spreads across the land as Castiel walks out of the forest.
Dean looks up at the sky and Crowley senses something is happening.
Kevin finds a map of the world that shows red lights spreading everywhere.
Dean looks up at the sky as angels start falling from the sky, their wings burning off them as they slam into the ground. When Sam wonders what's happening, Dean tells him that the angels are falling.