Anna Milton

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Name Anna Milton
Actor Julie McNiven
Dates
Location no fixed address
Occupation Angel
Episode(s) 4.09 I Know What You Did Last Summer
4.10 Heaven And Hell

Anna is an Angel who, dissatisfied and frustrated with being an angel, chose to relinquish her grace and be reborn human.

4.09 I Know What You Did Last Summer

Anna Milton is being held in a psychiatric institution (Connor Beverley Behavioral Medicine Center) because she has been trying to warn people the apocalypse is coming and she hears voices. She actually does hear voices - those of the angels. She knows that Lilith is trying to break The 66 Seals and release Lucifer. When a demon tries to kill her she manage to escape, seemingly using some form of psychic power in the process. She takes refuge in the church in which her father was a deacon.
Ruby alerts Sam and Dean to her plight and they track her down, after finding her parents dead. She recognises them, and says she has heard the angels talking about Dean, as the one who may save them. She reveals that some of them don't like Sam. The demon Alistair then appears. He is immune to Sam's powers, and beats Dean, who had encountered him in Hell. In the chaos, Ruby takes Anna to safety, even though Anna is scared because she can see Ruby's demon face.

Later, Sam and Dean meet up with Ruby and Anna. Castiel and Uriel arrive at their hideout to take Anna, with Castiel announcing "She has to die."

4.10 Heaven And Hell

With the help of Pamela Barnes, Anna is revealed to be an angel, a former superior of Castiel and Uriel, who chose to rip out her Grace and fall to Earth, where she was reborn as human. This disobedience is why the angels want to kill her.
Anna suggests that if she has her Grace restored she will be able to protect herself. Sam locates where Anna's grace fell to earth, but when they get there they find it has been taken. Anna then gets a messages from the angels demanding that she be turned over to them by midnight or Dean will be returned to Hell.
She speaks to Dean of her frustrations with being an angel, particularly the blind obedience to God and the lack of emotion. She reveals that she knows what Dean did in Hell and encourages him to forgive himself. She then kisses him, and they have sex in the Impala.
Later Uriel appears to Dean in a dream and reveals the he is carrying Anna's grace in a phial around his neck.
When Castiel and Uriel appear in person, it appears that Dean has betrayed Anna and is handing her over; however, it is part of a ruse to bring the angels and demons (in the form of Alistair and his henchdemons) together to rid the Winchesters of both. A fight ensues, during which Anna steals her grace back from Uriel. During her transformation back into an angel, which involves an overpowering white light, Alistair disappears. When the light subsides, Anna is also gone, presumably back to Heaven, where Dean imagines she is not happy.

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