|Title||I Know What You Did Last Summer|
|Episode #||Season 4, Episode 9|
|First aired||November 13, 2008|
|Directed by||Charles Beeson|
|Written by||Sera Gamble|
|On IMDB||I Know What You Did Last Summer|
|Outline||Sam and Dean meet Anna, a psychiatric patient who can hear angels and fight to protect her from demons.|
|Timeline||Two months after 4.01 Lazarus Rising|
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The episode begins with an interview between Anna Milton and her psychiatric counselor at the Connor Beverley Behavioral Medicine Center where Anna is being held because she hears voices and has attempted to warn people that the Apocalypse is coming. She states that there are over 600 seals, and Lilith only needs to break 66 seals to release Lucifer. When a demon tries to kill her, she manages to escape, using some form of psychic power in the process.
Ruby informs Sam and Dean that a woman called Anna Milton is being pursued by demons and they take off to find her, despite Dean's reluctance. They speak to her doctor at the hospital, and find out she had been talking about demons and the apocalypse. Her sketch book reveals she knew about the breaking of the seals. After finding her parents dead, the brothers track her to a church. Anna recognizes them, the voices she hears are those of the angels and she has heard them talking about Dean, as the one who may save them. She reveals some of them don't like Sam. Alastair 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. She can see the real face of every demon.
Dean demands Sam tell him why he trusts Ruby. In flashback we find out that Sam tried to trade himself for Dean with a crossroads demon. Lilith then released Ruby from Hell, on the condition that she kill Sam. She instead kills the demon with her and tells Sam she is there to help him. A grief-stricken Sam rejects her help, and demands she vacate the body she is possessing.
Ruby then possesses the body of a woman in a coma who is brain dead, and whose soul has left her body, and returns to Sam. She offers to help Sam use his powers so he can take revenge on Lilith and he accepts. He is unsuccessful at first in exorcising demons, and becomes even more despairing. Ruby tells him things will get better with time, and seduces him. After that, Sam finds omens that lead him to Lilith and he pursues her despite Ruby's warning not to. Sam walks into a trap, and he's attacked by two demons until he is rescued by Ruby. She kills one with her knife and Sam successfully exorcises the other. Ruby saved his life, Sam tells Dean.
Back in the present, Ruby possesses the body of a maid at the hotel where Sam and Dean are staying in order to warn them that demons are closing in on them. She passes them the address of the cabin where she left Anna, tells them to exit through the bathroom window and to leave the car, then departs. Shortly thereafter, Sam and Dean meet up with Ruby and Anna at the cabin. When they sense someone approaching they assume it is Alastair, and Ruby asks Sam and Dean where the knife is -- they have to admit that it was lost in the previous fight with Alastair. However, to their surprise, instead of a demon, Castiel and Uriel appear and demand that they hand over Anna, with Castiel announcing, "We're here for Anna... she has to die."
- "The Blues Won't Let Me Be" by Left Hand Frank and His Blues Band
- (plays while Dean tries to stop Sam from betting)