A young woman, Anna Milton, is confined at a mental hospital as her psychiatrist tries to get her to explain what she did. Anna says that she tried to warn everyone of what she now knows to be true: that the Apocalypse is coming. Anna tells her psychiatrist how a demon, Lilith, is going to free Lucifer by unlocking 66 of the 600 Seals, and that even the angels can't stop him. Once Lucifer is freed, the Apocalypse will arrive and they'll die.
That night, an orderly brings Anna her medication but Anna recoils in terror, seeing something beneath his normal face. His eyes turn black and he admits he's there to kill her. Anna uses some power to shove a metal case into the orderly and crush him against the door. She then slips out and escapes.
Sam is at a bar, drunk and playing pool. Dean tries to discourage him but Sam isn't as drunk as he looks and hustles his opponent. However, he breaks off the game when he and Dean see Ruby at the bar. Dean doesn't trust her but she informs them that Anna escaped and the demons want her back alive. Dean doesn't trust Ruby but Sam does and they leave to check out the story. En route, Dean questions Sam's involvement with a demon and Sam refuses to talk to him about it. When Dean pushes it, Sam asks him to talk about his time in Hell and Dean shuts up.
Six months ago: Sam tries to summon a crossroads demon and offer his life in return for Dean's. The demon refuses and Sam pins him to a metal barrel by his hand, using the demon-killing knife. The demon still refuses to bargain, saying that Dean is in Hell and that's exactly where Lilith wants him.
Dean and Sam talk to Anna's psychiatrist, who says the orderly was attacked from behind as part of Anna's planned escape and doesn't remember anything. They don't believe it and ask what happened to Anna. The psychiatrist explains that Anna, the daughter of a church deacon, just flipped one day and started talking about hearing voices and seeing demons, so her father had her institutionalized. The brothers go through Anna's papers and finds drawings of the two Seals they've dealt with, the Raising of the Witness and the freeing of Samhain. They go to see Anna's parents but they're dead: the demons got there first. Dean spots a photo of Anna's church and recognizes the windows from her drawings. They go there and find Anna in hiding. She know them, saying she's heard the angels talk about them. They confirm that she can overhear angels talking, and she first received her "gift" on the day that Dean was taken from Hell.
Ruby barges in and warns them that a big-time demon followed them from the house to the church. They hide Anna in a closet as a statue of Jesus starts crying tears of blood. Over Dean's objections, Ruby warns that Sam will need to use his powers. The demon, possessing a male body, bursts in and it proves immune to Sam's powers. It throws Sam down the stairs and stops Dean from stabbing it with the knife. It knocks the knife out of Dean's hand asks if he remembers him. Ruby gets Anna out of the church and Dean finally realizes who the demon is: his tormentor in Hell. Sam climbs up the stairs and stabs the demon with the knife, but it's only injured. They're forced to leap out a window, leaving the knife behind.
At their motel, Sam and Dean tend to their wounds. Sam wonders who the demon is and Dean hides his knowledge. Dean is concerned about where Anna is and whether Ruby can be trusted. Sam still trusts her and figures she's keeping Anna hidden and can't risk telling them without the demons following them again. Dean wonders why Sam trusts Ruby and Sam admits that Ruby saved his life.
Six months ago: Sam returns to his motel room after a night of drinking. Two demons, male and female, attack and restrain him. The female says she's Ruby and Lilith has given her chance to redeem herself. Sam tells her to go ahead and kill him and Ruby uses the demon-killing knife to stab... her partner. She tells Sam they have to go and they hit the road. She explains that she's now a fugitive and went through unspeakable torture at Lilith's hands. Sam, unimpressed, wants to know if she can help save Dean and she admits there's no power strong enough to do so. He pulls over and tells her to abandon the living host she's inhabiting, or he'll kill her.
A Jane Doe is dying in a hospital and the doctor signs the death certificate as she passes away. The body suddenly comes to life and asks for food. Ruby finds Sam and shows him the death certificate, then says she can help him kill Lilith. He wants to go after the demon right away but she says that once he sobers up they'll need to work out plan and take things carefully.
Sam practices his powers on a captive demon but is unable to send it back to Hell. Ruby disposes of it with the knife and says she understands from when she was human what it means to lose someone. She starts to kiss Sam and he shoves her away, but she refuses to back off and they end up making love.
Dean tells Sam that's more information then he needs to hear. Sam skips on to how he found signs of Lilith...
Five months earlier: Sam prepares to go after Lilith but Ruby warns they're not ready. When he ignores her, she figures he's trying to kill himself out of grief and guilt. Sam leaves and goes to the house where he's traced Lilith. He finds a little girl but she's normal: two demons have used the girl as bait. They capture Sam and take the knife. They prepare to kill Sam but Ruby arrives, grabs the knife, and kills one of them. The other one overpowers her and prepares to kill her with the knife, but Sam uses his powers successfully and expels it from the host body and sends its essence back to Hell.
Sam explains that he couldn't have survived without Ruby, who inspired him to live... just the way Dean would have. A made knocks on the door and delivers towels, but then says she's Ruby temporarily in a new host body. She gives them an address and leaves, and the brothers slip out the back. They go to the cabin where Ruby is hiding Anna. Dean apologizes to Ruby for distrusting her, and Anna wants to call her parents. Sam finally tells her what happened and Anna starts to break down, but then says "they're coming." They try to fortify the place and have to explain to Ruby they've lost the knife.
There's a knock on the door, which then bursts in. Castiel and Uriel stride in and demand to know where Anna is. The brothers wonder exactly what they're for, and Castiel explains that they have been told to kill the girl.
(to be continued)
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