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[[Dean]] and [[Sam]] are driving through the night from [[Pamela]]'s funeral and Sam tells Dean that [[Ruby]] is going to meet them after tracking some leads. Dean says he doesn't care and is feeling guilty and becoming tired of losing all of their friends. Sam tells him to get angry, not tired. They check into a motel and find [[Uriel]] and Castiel waiting for them. Dean snaps at them and Uriel is less than sympathetic. Castiel expresses his sympathy but Uriel puts him in his place. He then informs the brothers that seven angels have been killed and they don't know how the demons are doing it. They want Dean to interrogate [[Alastair]], their captive. Dean refuses but Uriel tells him they're not asking. The [[angels]] disappear with Dean, leaving Sam behind.
Castiel shows Dean Alastair, bound within a [[devil's trap]] in an empty warehouse. Dean tries to leave but Uriel blocks him. Castiel says they have no choice but to ask and Dean asks to speak to Castiel alone. Uriel leaves and Castiel warns that his superiors are beginning to doubt him because of his sympathies toward humans. Dean warns that Castiel won't like what walks out if Dean goes in to torture Alastair. Castiel assures him he'd give everything for Dean not to have to do it.
Dean goes into the chamber alone. Alastair starts singing as Dean starts preparing prepares a collection of torture instruments. Alastair laughs and wonders if Dean is scared. Dean denies it and Alastair points out Dean left part of himself back in the pit. He suggests Dean might want to get revenge -- if not for how Alastair tortured Dean, then for everything he did to [[John Winchester]].
Ruby arrives at the motel and doesn't see the problem, but Sam warns that Dean can't get the job done. HeDean's not strong enough any more, but Sam says he'll be strong enough to do itinstead.
Alastair boasts of what he did to John but admits he never did break him the way he broke Dean. Dean tells him that he could still dream in Hell, and he dreamed of torturing him. He started starts with a syringe filled with holy water. Outside, Castiel listens to Alastair's screams of pain.
At the motel, Ruby conducts a ritual while burning a map to locate Dean. Sam says he "needs it" and it's been weeks. Ruby tells him it'll be okay, then cuts herself on the her arm. He Sam eagerly sucks the blood from her. Dean coats the [[Ruby's Knife|demon-killing knife]] with [[holy water]] and Alastair asks if the torture will give him closure. Dean plunges the knife into Alastair, but the [[demon]] still boasts of how he changed Dean and there's no going back. Dean admits he's right, but now it's his turn. He's unaware that a water valve is moving by itself and water is dripping on the devil's trap.
Outside, Castiel sees the lights flickers flicker and realizes that [[Anna]] has arrived. She's created a duplicate of her human body. Castiel warns that he still has orders to kill her, but she's sure confident he won't. She asks why they're letting Dean do this and questions if torturing is God's work. Castiel refuses to question the will of God, but Anna questions whether the orders are coming from God. Anna She points out that he's feeling doubt and insists the orders are wrong. She suggests they can act together, but he insists that he's nothing like her. He tells her to go and she disappears.
Alastair still refuses to give the angel-killer's name. He explains that [[Lilith]] had a particular reason to get Dean, but Dean shuts him up by pouring [[salt]] in his mouth.
As Sam drives through the night, Alastair explains that John was supposed to bring it on but it turned out that it was Dean. He describes how the first person Dean tortured was the first seal. When he broke, it broke. Alastair points out that when they summon the Apocalypse, it'll be Dean's fault. Alastair focuses on the water pipe as it continues to drip on the seal. Dean figures that Alastair is telling the truth but warns he won't be there to see it. When he turns, Alastair is free and attacks Dean. The demon hits him repeatedly until Castiel arrives, plunging the demon-killing knife into his shoulder. Castiel twists the knife but Alastair manages to pull it out and lunges at the angel. The two fight while Dean lies unconscious on the floor unconscious.
Alastair slams Castiel back onto a hook, then admits all he can do is send Castiel back to Heaven. The demon starts to recite an incantation as Castiel glows with white light. Suddenly Alastair chokes and falls back as Sam arrives, using his powers to pin Alastair to the wall. Sam demands the name of the angel-killer and tortures him. Alastair says he doesn't know and finally admits the demons are not killing the angels and Lilith wouldn't stop at just seven angels. Alastair dares Sam to send him back but Sam tells him he can kill demons now. He focuses his powers and destroys the demon once and for all. Castiel just stares at Sam in shock.
Sam gets Dean to the hospital and sits at his bed side. Castiel meets him outside and Sam tells him to heal Dean. Castiel apologizes, saying the trap shouldn't have broken. Sam insists that Alastair wasn't lying and they need to find out who or what is killing the angels.
Uriel is in an empty park when Castiel arrives. Uriel says he's received revelation that they've re to stop hunting the demons. Even Uriel realizes something is wrong in Heaven and they wonder who could be responsible. Castiel wonders if God is punishing them, or if God isn't giving the orders any more. Uriel disappears, saying he won't wait to be gutted.
That night, Castiel calls out to Anna and she comes. He admits he's considering disobedience but she warns that it gets worse as he exerts his independence. He flinches when she touches him, but Castiel begs her to tell him what to do. Anna refuses, telling him it's time to think for himself. He looks at a nearby drinking fountain and sees a water valve.
