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===[[4.09 I Know What You Did Last Summer]]===
Sam Alastair leaves [[Hell]] and [[Possession|possesses]] a pediatrician to capture and Dean find interrogate [[Anna Milton]] hiding in her church. He follows [[RubySam]] appears and tells them [[Dean]] from Anna's house to run because a powerful the church Anna is hiding at. [[demonRuby]] tries to get Sam, Dean, and Anna to leave as quickly as possible to avoid Alastair, but realizes that it is approaching. Suddenly too late when signs of the demon's his approach break out, including a statue of the virgin Mary weeping blood. Alastair arrives. Although she convinces Sam attempts to exorcise him Alastair with his powers, but to no they have little effect. Dean fights with on Alastair, who asks if uses [[telekinesis]] to fling Sam down the staircase before attacking and overpowering Dean recognizes him{{Quotation|title=|text= '''Alastair:''' Hello again, He taunts Dean. Come onabout their "closeness" in Hell, prompting Dean. Don't you to finally recognize me? OhAlastair,I forgot -- I'm wearing a pediatrician. But we were so close... In Hell.<br>'''Dean:''' Alastair.|author= Alastair and even in his [[Deanmeatsuit]]|source= [[4.09 I Know What You Did Last Summer]]}} Sam stabs the [[demon]] returns to stab Alastair with [[Ruby's knife]], but he is unharmedmuch to the Winchesters' horror, the [[demon]] does not die. As Alastair pulls the knife out, Sam and Dean escape flee from him by jumping out the church windowand he allows them to escape so that he can use them to lead him to Anna again.
===[[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 tells [[Sam]] that Alastair is "practically the Grand Inquisitor" in [[crossroadsHell]] where and that she tries to make a deal with him: giving more scared of him than even [[angels]]. She suggests that he resume drinking [[Anna Miltondemon blood]] so that he can exorcise Alastair, but Sam refuses. Later on, Ruby fulfills her part in exchange for allowing Sam's plan by letting Alastair find her and the Winchesters to go free. He then makes Alastair derides her for protecting Anna, an [[angel]], when she is a counter [[demon]], and rejects her offerto trade him Anna for the safety of herself, Sam, and [[Dean]], instead capturing her and torturing her with [[Ruby's knife|her own knife]] to force her to tell him where Anna is. He later has a showdown While torturing her, Alastair reveals that he actually vastly prefers Hell to Earth (which he loathes), having only left it because he must deal with "this nasty angel business." Eventually, Ruby leads him and his minions to Anna; she is unwilling to simply tell him what he wants to know because she knows that he would just kill her afterwards. Alastair and his minions find that [[Castiel]] and [[Uriel]] in which he overpowers are also at the site and are about to execute Anna. Dismissing Castiel's warnings that they will be killed if they do not leave, but is distracted the [[demon]]s fight the angels to stop them from harming killing Anna. Although Alastair's minions are quickly killed by Uriel, Alastair proves too powerful for Castiel to smite and overpowers the angel. When Dean hits him over the head with a crowbar, Alastair shifts his attentions to him by an attack from and Sam and launches a [[DeanTelekinesis|telekinetic]]attack on their internal organs while chastising Dean about his lost "potential. The fight is interrupted " He tries to intervene when he sees Anna reacquires regain her [[grace]] from Uriel, she and Alastair then both disappear in a flash of bright light with Alastair but gets vaporized instead, leaving behind only Ruby's knife. Later, Dean tearfully reveals to Sam that after every day of torture in Hell, Alastair would offer to stop if Dean agreed to torture other souls; although Dean initially refused, he eventually gave in because he couldn't take it anymore.
===[[4.15 Death Takes a Holiday]]===
===[[4.21 When the Levee Breaks]]===
While withdrawing undergoing forced withdrawal from the [[demon blood]], [[Sam]] has several hallucinations, the first of which is Alastair inexplicably returning. Sam hallucinates that he is being strapped down and tortured by Alastairwith a knife, but eventually Alastair disappears and Sam realizes that he is hallucinating.
===[[4.22 Lucifer Rising]]===
===[[6.10 Caged Heat]]===
To prove that she is capable of making [[Crowley]] give into her demands, [[Meg]] reveals that she had apprenticed under Alastair in [[Hell]] like [[Dean]] had, and Dean grudgingly concedes that this means she can make Crowley do whatever she wants. Meg doesn't reveal when she undertook this apprenticeship, but it must have been before Alastair's capture in [[4.15 Death Takes a Holiday]], as he was killed in [[4.16 On the Head of a Pin|the following episode]].
===[[6.20 The Man Who Would Be King]]===

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