Having grown to hate her life as an angel, Anna decided to cut out her grace and Fall which would allow her to be born as a human. Anna's grace landed separately to her in Union, Kentucky where it created a beautiful tree. At some unknown point, the grace was collected by Uriel who kept it in a vial around his neck. Anna was born to human parents Richard and Amy Milton who had believed themselves unable to have a child. Remembering her life as an angel, Anna was afraid that her father would come after her for her actions, but eventually forgot any other life she lived other than that of a human.
On September 18, 2008, Dean Winchester was raised from Hell by the angel Castiel. For the first time since Falling, Anna heard the angels again, hearing them state that "Dean Winchester is saved." Anna then regained the ability to tune in to "angel radio" and learned a great deal about the Winchesters and the Apocalypse. Anna's ramblings about the end of the world got her committed to Connor Beverly Behavioral Medicine Center where she was diagnosed with schizophrenia. While there, Anna made a sketchbook pertaining to the 66 Seals and tried to convince others of the very real threat of Lilith breaking them to no avail. However, word of her ability to listen in on the angels got to the forces of Hell who sent Alastair to capture Anna so they could torture her information. Heaven also learned of Anna's state and dispatched Castiel and Uriel to kill her.
Shortly after Anna tells her psychologist about the 66 Seals, a demon possessing an orderly enters under the guise of delivering Anna's medication. As Anna faces him, she is able to see the demon's true face and he turns his eyes black as he taunts her. As the demon locks the door, Anna manages to telekinetically slam a dresser into the demon, slamming him against the door and knocking him out. Terrified, Anna quickly flees her room and the hospital. The demon leaves his vessel afterwards, leaving the man with no memory of his possession.
The next night, while hustling pool at a bar, hunters Sam and Dean Winchester are approached by the demon Ruby who is working with Sam to hunt Lilith. While Dean is skeptical and untrusting of Ruby, she tells Sam about the demons going after Anna. While Ruby doesn't know why they want Anna, she knows that "real heavy-hitters" are going after her and the order is to capture her alive, causing Ruby to think it might be something the Winchesters would be interested in. While Dean is uninterested, Sam insists upon them taking the case even though its a three day drive away.
Arriving at the Connor Beverly Behavioral Medicine Center where Anna had escaped from, the Winchesters learn from Anna's psychologist that they believe Anna planned the escape and ambushed the orderly who has no memory of even entering the room. The psychologist tells the Winchesters how until two months before, Anna was a normal girl before her schizophrenia came on and hands them Anna's sketchbook. The Winchesters are shocked to find sketches mentioning the Rising of the Witnesses and the raising of Samhain. The psychologist also informs them about how Anna believed that Lucifer would rise and end the world, further shocking them with the depth of information Anna apparently has access to about what the demons are up to.
Deciding to see if they can learn anything from Anna's parents, the Winchesters visit the Milton's home only to find Richard and Amy Milton dead on the floor with their throats slit. Finding sulfur, they quickly realize that the demons had beaten them to the Milton's and killed them. Looking at the pictures on the mantle, Sam finds one of the family in front of the church Richard was a deacon at and notes that the stained glass window of the church matches a window drawn repeatedly in Anna's sketches. Seeing this, the Winchesters suspect that the religious, scared girl being chased by demons fled to her church.
In the attic of the church, the Winchesters find Anna who recognizes their names from what she has overheard the angels talking about. Anna explains to the Winchesters that she can sometimes hear what the angels are discussing and have been able to since she heard "Dean Winchester is saved" on September 18th though Anna doubts the angels even know she exists. The Winchesters realize that the demons are after Anna as with her ability to overhear "angel radio", they can learn what the angels are up to.
As Anna asks about her parents, Ruby bursts in, scaring Anna who can see Ruby's true face. Ruby warns that a demon "big-timer" is coming and they have to flee. Dean is skeptical due to the timing, believing that Ruby had led the demon to them, but Ruby states that the demon had followed them from Anna's house and they must go now. However, Sam notices that a statue of the Virgin Mary is weeping blood and Ruby realizes that its too late to flee. Sam hides Anna in a closet, but when he draws a flask of holy water, Ruby tells Sam that he has to use his powers to exorcise the demon right away. While Dean doesn't like the idea, Ruby insists that if Sam doesn't use his powers on the demon right away, they will die.
When the white-eyed demon bursts into the room, Sam attempts to use his power to exorcise him, but it has no effect on the demon. The demon taunts that Sam doesn't have "the juice" to take him on and telekinetically flings Sam down the stairs. Dean attempts to attack the demon with the demon-killing knife, but the demon easily restrains him and disarms Dean. As the demon beats on Dean, Ruby gets Anna out of the closet and flees with her. The demon pins Dean to a support beam and beats on him and expresses surprise that Dean doesn't recognize him despite the demon wearing a pediatrician. After the demon comments that "we were so close, in Hell", Dean recognizes him as Alastair to Dean's horror. As Alastair taunts Dean, Sam grabs the demon-killing knife and stabs Alastair in the chest with it. However, the knife fails to kill Alastair who tells Sam that he will "have to try a whole lot harder than that" to kill him. Alastair shoves Sam away and is left in great pain from the knife which he quickly removes. As Alastair is distracted by his knife wound, Sam grabs Dean and they jump out the stained glass window of the church. Alastair watches him them go once they are out the window, making no move to stop them and is left with the demon-killing knife.
After the fight at the church, the Winchesters retreat to a motel room where they treat Sam's cut arm and Dean's dislocated shoulder. Sam recognizes that killing them would've been no problem for Alastair and he let them go to follow them to Anna. Sam is insistent on waiting for Ruby to find a safe way to contact them and is forced to explain to Dean what happened while Dean was in Hell that has caused Sam to trust Ruby so much.
Moments after Sam finishes his story, a maid enters. The maid gives a confused Sam the address she is at and orders them to go out the bathroom window and not stop or take their car as there are demons in the hallway and parking lot. Sam realizes that the maid is possessed by Ruby who tells him that her usual vessel is "slowly rotting on the floor" of the cabin she left Anna at. She orders them to go before departing herself.
The Winchesters are able to reach the cabin safely where they find Anna with Ruby in her usual vessel. Anna now trusts Ruby who she recognizes as not being like other demons since Ruby saved her life. As Dean awkwardly attempts to make amends with Ruby, Anna asks to be able to call her parents and let them know that she's okay. As Sam tries to find a way to tell her that they are dead, Anna realizes what happened to them from Sam's reaction to her question and breaks down in tears.
Anna suddenly senses something and announces that "they're coming." As the lights flicker, Dean has Sam take Anna into the cabin's backroom while Ruby secures the doors. As the Winchesters arm up, Ruby discovers that the demon-killing knife is gone to her anger. Moments later, one of the doors bursts open and to the group's surprise, instead of demons, the angels Castiel and Uriel enter. Uriel is disgusted to see Ruby due to his hatred of demons and Castiel states that they are there for Anna. To the shock of the Winchesters, Castiel states that the angels are not there to help Anna but to kill her, that "she has to die."
The Winchesters are shocked by the demands of the angels and are ordered out of the way by Uriel who promises to "kill her gentle." Castiel is unmoved by Dean calling them heartless and states that Anna is "far from innocent." Uriel calls Anna worse than Ruby and demands that they give them Anna. Dean refuses and Uriel asks who will stop the angels: them or Ruby who he throws across the cabin into a window. Dean attempts to attack Uriel as he goes to smite Ruby, but Uriel easily stops the blow and starts beating on Dean. With Uriel handling Dean and Ruby, Castiel makes his way towards the backroom and puts Sam to sleep when he gets in the way. Before Castiel can get into the room where Anna is located, he and Uriel are suddenly banished from the cabin.
Recovering, the Winchesters and Ruby enter the backroom where they find that Anna has slit her wrists and drawn an angel banishing sigil on the mirror. Anna tells Dean that she didn't kill the angels but sent them "far away." She also has no idea how she knew how to make the sigil, stating that it just popped into her head. "I don't know how I did it, I just did" a confused and dazed Anna explains. As Ruby tends to Anna, the Winchesters discuss the situation and how the angels obviously want Anna for more than her ability to hear them and her blood spell is serious magic. Realizing that something is going on with Anna, Dean orders Sam to see if he can find out anything while Dean takes Ruby and Anna someplace safe before the angels return.
Dean takes Anna and Ruby to Bobby's house in order to use his demon-proof panic room to protect them. Ruby is also able to provide the group with hex bags to hide their location from everyone, including demons and angels. In the meantime, Sam retrieves the Impala and gets Anna's psychiatric records. Sam shows Dean that when Anna was two and a half, she had a psychiatric episode where she insisted that Richard Milton wasn't her father and that her real father was angry enough to kill her before eventually getting better until she started hearing "angel radio." Having overheard the conversation, Anna angrily confronted the Winchesters over not simply asking her and going behind her back. Recognizing that Anna is right, Sam asks if she knows what the angels are talking about when they say that she is guilty of something, but a distraught Anna has no idea. Sam then suggests bringing in psychic Pamela Barnes to help them find the answers.
Dean is able to get Pamela to come as Pamela is excited to do anything that will "dick over an angel" as Castiel burned her eyes out. Inside the panic room, Pamela places Anna under hypnosis and asks how she can hear the angels and knew how to perform the banishing spell, but Anna doesn't know. Pamela questions Anna on her father and after Anna names Richard Milton as her father, Pamela asks Anna to look back to when she was two years old and tell them her real father's name and why he she believed he wanted to kill her. After some resistance, Anna looks back and suddenly starts screaming in a panic that her father is going to kill her, causing all of the lightbulbs in the room to shatter, the door to close and lock and for Anna to knock Dean backwards so hard he destroys a chair upon landing. Pamela is able to quickly calm Anna and awaken her from the hypnotic state. Upon awakening, Anna thanks Pamela for her help, stating that Pamela has helped Anna remember who she is. "I'm an angel," Anna tells her stunned and confused audience.
Moving to Bobby's study, Anna reassures the group that she is not like the other angels, though it doesn't make Pamela or Ruby feel better. Anna recognizes Castiel and Uriel as the ones who are chasing her and reveals that she used to be their boss but the angels now want her dead as she disobeyed and Fell. Anna and Pamela explain that it means that Anna cut out her grace and fell to Earth where she was born as a human. While she initially remembered her true nature, the older she got as a human, she repressed those memories until Pamela awoke them again. A panicked Ruby tells Anna that she's completely screwed: Heaven wants Anna dead while Hell wants her as she is a flesh and blood angel they can torture for information. Anna acknowledges the truth of Ruby's statement and tells the others that she has decided to reclaim her grace and become an angel again. However, Anna doesn't know where to find her grace as she was falling from the sky too fast. After Anna confirms that she was falling in a way that the human eye could see, Sam decides to look for comets or meteor that may have been spotted around the time Anna fell for clues. Wanting nothing more to do with the situation, Pamela has Dean take her home.
Sam is eventually able to find records of a meteor spotted in the part of Ohio that Anna was born in March, 1985. As this was nine months before Anna's birth, Sam suspects this was Anna. Sam is able to find a record of another meteor at the same time in Kentucky that he believes is Anna's grace. Sam shows his findings to a skeptical Ruby who apologizes for bringing this problem to him, feeling that she has brought them into an impossible situation where either the angels or the demons will get them. Ruby reveals that she fears Alastair more than she does the angels, calling him the "Grand Inquisitor" of Hell and "Picasso with a razor." Ruby tells Sam that he needs to use his abilities to throw Alastair back in the Pit and states that he has been getting "flabby" from not using them. Sam refuses to do something that he needs to do to get his abilities working right again and Ruby tells him that he'd "better hope that Anna gets her groove back or we're all dead."
Returning from bringing Pamela home, Dean asks Anna about why the angels brought him back, but Anna doesn't know as the angels aren't talking about it and the order was given after she left. Anna reveals that she hated being an angel and envied humanity's ability to feel things, especially emotion and its why she Fell: she wanted to be able to experience the things humans can. Anna tells Dean that only four angels have ever actually seen God and the other angels have to act on faith that he exists which they are killed for not doing. Anna describes her life as an angel, causing Dean to see parallels between his own life and hers and to sympathize with her situation.
As Dean and Anna finish talking, Sam approaches with the news that he has found something. On a map, Sam shows Dean, Anna and Ruby a location outside of Union, Kentucky where in 1985, there had been an empty field before a full-grown oak tree that appears at least a century old grew over the course of six months. Anna recognizes that its possible for the grace to have caused this as "grace Ground Zero" is "pure Creation" instead of destruction. Arriving at the oak tree the next day, Anna is able to sense that it is in fact where the grace touched down. However, when Anna approaches the tree and touches it, she is able to sense that the grace is no longer there and that someone had taken it.
That night, after retreating to a barn in the area, Sam, Dean and Ruby argue over what to do now. Dean suggests retreating to the panic room once again protected by their hex bags, but Ruby feels that while they can fight either Heaven or Hell and maybe win, if they try to fight both they will lose. Anna interrupts them to alert the others that there is a message playing on "angel radio" on a loop: "Dean Winchester gives us Anna by midnight or we hurl him back to Damnation." Sam asks Anna if she knows of any weapon that can kill an angel, but she tells him that there's not one they can get to right now. Dean suggests calling Bobby back from his vacation for help, but Sam feels that Bobby can't tell them anything that they don't already know. Dean insists that they need to come up with something to protect Anna.
Later that night, as Dean examines lore by lantern light on the Impala, Anna visits him to thank Dean for trying to help her. Anna expresses doubt about whether or not she deserves to be saved, comparing her actions to Lucifer's. Dean consoles her and Anna reveals that she knows what Dean did in Hell. While Dean is unwilling to talk about it, Anna tells Dean that he needs to forgive himself for his actions and that when he is ready to talk, there will be people there ready to listen. Anna kisses Dean and the two end up having sex in the backseat of the Impala.
At the same time, as Sam sleeps, Ruby leaves and goes to a crossroads where she burns her hex bag. Alastair appears almost immediately, disgusted by the idea of a demon protecting an angel. Ruby acknowledges that she "hasn't exactly been Employee of the Month," but states that she never wanted to get in the middle of a conflict between angels and demons. As a result, Ruby offers a deal: to give up Anna to Alastair if he leaves her and the Winchesters alone in exchange. Instead, Alastair has Ruby apprehended by two henchman so he can make her "a counter-offer."
As Dean sleeps, he is greeted by Uriel in a dream of the barn. Dean quickly realizes that he is dreaming and that Uriel has entered his dreams to talk to him, something Uriel confirms. Uriel states that Castiel is not there as Castiel has a weakness in that he actually likes Dean. Uriel states that their time is up, but Dean claims that Anna has regained her grace and is an angel once more. An amused Uriel reveals that he has Anna's grace in a vial around his neck because "we can't let Hell get their hooks into her." Dean asks Uriel to simply return Anna's grace to her, but he refuses as Anna has committed a crime and must be punished. An amused Uriel realizes that Dean has had sex with Anna and demands Dean hand her over or get thrown back into Hell. Dean refuses, knowing that the angels need him for something. Uriel claims that the situation with Anna is even bigger than their plans for Dean and he can be replaced, but Dean defiantly tells Uriel to go ahead and throw him into Hell if he wants. An amused Uriel realizes Dean means it and when Dean states he won't break easily, Uriel tells him that he just need to find "the right pressure."
At the same time, Alastair brutally tortures Ruby with the demon-killing knife for the location of Anna. When he removes the gag preventing her from "smoking out," Ruby refuses to tell him as she knows he will then kill her. Instead, Ruby promises to show Alastair where to look.
The next morning, Sam nervously wonders what's taking Ruby so long while Dean drinks heavily from a flask. As they wait for Ruby, Castiel and Uriel enter and Castiel reveals that Dean gave Anna up. Anna realizes that the angels gave Dean an ultimatum: either allow them to kill Anna or they would kill Sam instead. Anna gives Dean her forgiveness and kisses him before facing the angels, saying that she's ready. Castiel offers his apologies to Anna, but she tells him that he's not really sorry as he doesn't know the feeling. Castiel acknowledges this, stating that they have a history but "orders are orders. I know," Anna finishes. She asks Castiel to make it quick.
Before the angels can kill Anna, Alastair, his two henchmen and a heavily-injured Ruby appear behind the Winchesters to interrupt the confrontation. The angels and demons face off with Uriel and Alastair exchanging insults. Alastair promises to leave if they give him Anna and to "make sure she's punished, good and proper." Castiel demands once more that Alastair leave or the angels will lay the demons to waste, but Alastair is willing to take his chances.
With the demons unwilling to leave, Uriel starts a fight by attacking one of Alastair's henchmen and slamming him up against a wooden support beam. Though the other demon tries to intervene, Uriel effortlessly knocks him to the ground. Castiel attacks Alastair, but his punches have no effect. Castiel then attempts to smite him, but the demon proves to be immune and mocks Castiel before knocking him to the ground. As Uriel smites the henchman he had been grappling with, Alastair begins casting a spell upon Castiel. Before Alastair can complete the spell, Dean whacks him in the face with a crowbar, pulling Alastair's attention away from Castiel but not otherwise harming him. Alastair tells Dean that he is disappointed as Dean "had such promise." As Sam stares at his brother in shock, Alastair causes the Winchesters to clutch their chests in pain.
As Uriel smites the second henchman, Anna takes the opportunity to snatch the vial of her grace from around his neck and smash it to the ground. Yelling at everyone to shut their eyes, Anna reabsorbs her grace and begins glowing from within. As the Winchesters and Ruby cover their eyes, Anna explodes into a blast of white light with a yell. As Anna explodes into white light, Alastair walks into it and is disintegrated, apparently killing the powerful demon.
Retrieving the demon-killing knife from where it was left on the ground when Alastair was disintegrated, Dean challenges the angels to go after Anna unless they're scared. While Uriel angrily claims that it isn't over, he's held back by Castiel and the two angels depart. After the angels are gone, its revealed that Sam's plan to protect Anna was to bring the angels and demons together and let them fight it out amongst themselves. While Sam thinks that Anna must be happy to be "some big-time angel" again, Dean knows that this isn't the case at all.
While Alastair is believed to have been killed by the light Anna gave off when she reabsorbed her grace, he is later revealed to have survived, telling the Winchesters that only his vessel was disintegrated while the demon himself survived.
While Anna becomes an angel again, she remains on the run from the other angels, though she later reappears to help Castiel against Uriel and to warn the Winchesters that Jimmy Novak is in danger. After being captured when Castiel turns her in following his own punishment, Anna tries to avert the Apocalypse by preventing Sam from ever being born and is killed by the archangel Michael.
- During this fight, Anna introduces the angel banishing sigil by using it on Castiel and Uriel. This sigil goes on to become a common defense against angels. It is ironically later used against Anna herself by Sam Winchester.
- This is the first time the Winchesters have fought against angels. As a result, they don't know what they are doing or how to properly fight them. The Winchesters later gain ways to banish, trap and even kill angels.
- Of the combatants in this fight, only the Winchesters themselves don't end up becoming enemies for at least a time on the show. Alastair, Ruby, Anna, Castiel and Uriel all show up as antagonists at some point or another.
- Uriel smiting two of Alastair's Henchmen during the barn fight is the first on-screen smiting on Supernatural. Castiel smote two demons off-screen in Lazarus Rising.