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===[[4.10 Heaven and Hell]]===
[[File:Alistair with Death's weapon.Jpg|300px|thumb|right|Alastair in his new [[meatsuit]], preparing to break one of [[the 66 Seals]].]]
Alastair appears again to [[Ruby]] at a [[crossroads]] where she tries to make a deal with him: giving him [[Anna Milton]] in exchange for allowing her and the Winchesters to go free. He then makes her a counter offer, capturing and torturing her with her knife. He later has a showdown with [[Castiel]] and [[Uriel]] in which he overpowers Castiel, but is distracted from harming him by an attack from [[Dean]]. The fight is interrupted when Anna reacquires her [[grace]] from Uriel, she and Alastair then both disappear in a flash of bright light with Alastair leaving behind only Ruby's knife.
[[File:Alistair with Death's weapon.Jpg|300px|thumb|left|Alastair in his new [[meatsuit]].]]
===[[4.15 Death Takes a Holiday]]===
Alastair is attempting to break one of [[the 66 Seals]] by killing two [[reaper]]s under a solstice moon. He confronts [[Dean]] and [[Sam]] in a cemetery, and injures Dean, but Sam is resistant to his powers and fights back. Alastair reveals that while his [[meatsuit]] was destroyed by [[Anna]], he himself survived. He flees when Sam tries to [[exorcise]] him with his powers and later returns in yet another meatsuit. When the boys become non-corporeal, and therefore subject to [[ghost]]ly weaknesses, they track Alastair down at a funeral home and he traps them with an iron chain. He kills one [[reaper]], but the boys rescue [[Tessa]]. Later as he confronts Dean, Alastair is captured by [[Castiel]].
[[image:Supernatural-04x16-OnTheHeadOfAPin.jpg|300px|right|thumb|Alastair being tortured by [[Dean]].]]
===[[4.16 On the Head of a Pin]]===
Alastair is captured by [[Castiel]] and [[Uriel]] and imprisoned in a [[devil's trap]], but he refuses to tell them anything about the slain [[angel]]s. [[Dean]] is recruited as an interrogator because he was formerly Alastair's student during his time in [[Hell]]. After extensive torture, Alastair breaks free Uriel having sabotaged the devil's trap to prevent his role in the angelic deaths being revealed. He almost kills Dean, but is stopped by Castiel, who throws [[Ruby's knife]] and embeds it in Alastair's chest. Alastair pulls the knife out and fights Castiel. He manages to trap him against a pillar, and admits that while he is unable to kill the [[angel]], he will send him back to [[Heaven]]. Alastair begins to chant, but he is stopped by Sam, who has become strong enough to overpower him with ease. Sam forces Alastair to talk, then kills him via his abilities.
|[[File:AlastairKnife416.jpg|thumb|400px|Alastair survives being stabbed with [[Ruby's knife]].]]
|[[File:AlastairKilled.jpg|thumb|400px|Alastair is killed by [[Sam]].]]
===[[4.21 When the Levee Breaks]]===

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