Uriel and Castiel confront the Winchesters and Ruby, and Uriel tells them to step aside: they're here to kill Anna. Dean accuses them of being heartless and Castiel agrees, but warns that Anna is far worse than a mere demon. When the brothers refuse, Uriel attacks ruby and smashes her aside. Dean attacks him and isn't able to inflict any harm, while Castiel renders Sam unconscious with a touch. Castiel reaches for the door leading to Anna's room but suddenly there's a burst of white light and he and Uriel are sucked away. Once everyone recovers, they check on Anna and find that she's used her own blood to draw a mystic symbol on a mirror, which cast the spell. She says she doesn’t know how she remembered the symbol or where it comes from.
Figuring the angels must consider Anna a threat for more than her ability to hear their conversations, the Winchesters get Anna to Bobby' s "panic room." Ruby gives them hex bags that will hide them from angels and demons. Dean thanks her, to her surprise, and compares notes with Sam. Sam has determined that when Anna was two and a half years old, she had hysterical outbursts where she claimed that her real father was angry at her. However, the incidents soon faded. Anna arrives and tells them to ask her rather than talking behind her back. They ask her what Castiel meant and she says she doesn’t know why they consider her such a threat.
The Winchesters need help and go get Pamela Barnes, the psychic who lost her sight to Castiel while helping them. She's eager to get revenge against the angels and uses hypnotic regression to take Anna back to her childhood. Anna insists that Rich Milton was her father and refuses to go back any further. When Pamela tries to continue, the panic room door slams shut and electricity fills the air. Dean tries to help Anna, who slams him into the wall. Pamela brings her out of her hypnotic state and Anna thanks her, saying she now remembers who and what she is: she's an angel.
Anna explains that she was a commander in the forces of Heaven, but disobeyed and ripped out her grace, her personal energy. She was then thrown down from Hell, where she reborn in her human mother's womb as a human child. As she grew older in human form, she forgot her memories of Heaven and who she was. Ruby explains they're in trouble: the demons want an angel to torture and Heaven can't risk her falling into infernal hands.
Anna says that if she can get her grace back, she can regain her powers and protect them. Sam figures she literally fell to Earth and does the research. He finds a report of a meteor that fell to Earth over Anna's hometown nine months before she was born, at the same time another meteor landed in Kentucky. They figure it's Anna's grace, and Sam starts trying to figure out where it landed. Ruby apologizes for telling them about Anna, since she was unaware it would stick them between the armies of Heaven and Hell. In private she talks to Sam and admits that she's frightened of Alastair, the demon leading the hunt for Anna. Ruby then notes that Sam will have to use his special abilities to stop Alastair, and that he's out of practice. He refuses and Ruby says that if he doesn't, they're doomed.
Dean returns after taking Pamela home. Anna is out in Bobby's junkyard and suggests that the Winchesters abandon her to save themselves. Dean admits they're not that smart, then asks why the angels pulled him out of Hell. Unfortunately, that happened after she fell and the angels aren't talking about it now. He wonders why she decided to become human and she talks about how she was "perfect" as an angel, but had no emotions or feelings. She hates what she was and doesn't want to go back. Worse, she explains that only four angels have seen the face of God and she wasn't one of them. She served for two thousand years on Earth, blindly obedient and taking her Father's existence on faith without ever receiving word of what he wanted or if he approved. Dean admits that he can sympathize.
Sam tracks down a story of an oak that grew almost-instantly in a field in Kentucky after the meteor was spotted. They head for Kentucky and find the oak, only to discover that her grace is no longer there.
They take shelter in a barn and Anna says she's receiving a new message: a "recording" saying that if Dean doesn't turn over Anna, he'll be cast into Hell. With time running out and no chance of finding a weapon, Anna talks to Dean outside and thanks him for his help. She then says that she heard the angels discussing what Dean did in Hell and he needs to forgive himself. Dean still refuses to discuss it. She says that when he does talk about it, his friends and brother will be there for him. Anna kisses him and they end up making love.
Ruby looks at the sleeping Sam and then somewhere far away. She burns her hex bag and Alastair appears behind her. He has the demon-killing knife and asks what she wants. She offers Alastair the girl, Anna, in return for freedom for her and the Winchesters. Instead he has his minions grab her and says he has an offer of his own.
Dean finds himself in a dream with Uriel, who tells him their time is up. Dean claims that Anna recovered her grace but Uriel reveals that he has it in a vial on a chain around his neck: they couldn't let her get it back and void her punishment. Dean refuses to turn her over and dares Uriel to throw him back into Hell. Uriel hesitates, and then says that there are other ways to force Dean to talk.
Alastair tortures ruby using the knife. As he talks about hating the cold and damp on Earth, he removes her gag and gives her a chance to talk. She refuses to give away Anna's location since he'll kill Ruby as soon as he gets what he wants. However, she does offer to show him where Anna is.
The next morning, Dean is drinking heavily as Sam wonders where Ruby is. Uriel and Castiel burst in and Sam realizes that Dean betrayed their location to the angels. Anna realizes what happens and explains that Uriel forced Dean to choose between her and Sam. She forgives him and kisses him, then tells the angelic duo that she's ready. Anna confronts them and says to do their worse, and disregards Castiel's attempt to apologize.
Alastair and his two demon minions arrive along with the bleeding Ruby. Alastair looks almost sadly at Dean, noting that he "had promise." Uriel tells him to get out and launches an attack when they refuse. Uriel dispatches one of the two minions while Castiel tries to sear Alastair's soul... and discovers his angelic powers have no effect. Alastair starts to chant an infernal ritual in Latin, telling Castiel it's time for him to leave, and Dean interrupts with an attack. Meanwhile, Uriel disposes of the second demon minion but Anna takes advantage of his distraction and grabs the grace from around his neck. She smashes it to the floor and the white energy flows back into her body. She tells everyone to close their eyes and then she and Alastair disappear in a blast of white light.
In the aftermath, Dean suggests the angels go find the now restored Anna. Uriel is ready to finish it but Castiel holds him back and the two disappear. Ruby comes over and it turns out Sam's plan was for her to give Alastair Anna's location, while Dean pretended to give in to Uriel. They hoped, rightly, that the two forces would be too busy fighting with each other. Sam figures that Anna is now happy as her old angelic self, but Dean knows better.
Later, the guys are drinking beer and Dean asks if Sam is curious about what Alastair said. Sam leave sit up to Dean to talk, and Dean explains that due to time distortion, he was actually in Hell for 40 years, not the four months that passed on Earth. Each day Alastair tortured him, flaying him down to nothing, then restoring him and doing it again... and again... and again. All Dean had to do to avoid his fate was take the knife and torture others. Dean, crying, explains that he held out for 30 years... and then took the knife. He tortured countless other souls to spare himself. Sam says that he held out longer than anyone else could have, but Dean admits that he'd rather not be able to feel anything rather than suffer with the memories of what he did.
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