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During this time, the Winchesters and Castiel search for [[Cain]] in hopes that he will know a cure for the Mark of Cain. Having been driven back under the Mark's influence by killing Abaddon's demons, Cain begins slaughtering all of his human descendants to get rid of his "cursed" bloodline. The discovery of this by Castiel causes the Winchesters, Castiel and Crowley to team up together to stop Cain once and for all. Using magic from Rowena, they are able to lure Cain into a [[devil's trap]], reducing his powers to the point that Dean can fight him. Though initially outmatched as he is unwilling to give into the Mark of Cain's power and rage, Dean manages to gain the upper hand and kills Cain with the First Blade. However, he hands the First Blade over to Castiel instead of keeping his promise to return it to Crowley, damaging Crowley's trust in Sam and Dean.<ref name="ten14" />
Enraged by Crowley kicking her out on the street,<ref name="ten17" /> Rowena demands that Sam kill Crowley in exchange for her help in decoding the ''[[Book of the Damned]]'' and getting a cure for Dean and the Mark of Cain and Sam agrees to the deal.<ref name="ten19" /> After [[Charlie Bradbury]] comes up with a way to read the ''Book of the Damned'', Rowena demands that Sam uphold their end of the deal before she will cure Dean. Sam is able to lure Crowley into a trap and immobilize him with a [[devil's trap bullet]], but Sam's attempt to kill Crowley with a spell provided by Rowena fails. Instead, Crowley, who has been trying to reshape Hell for the better, is reminded of his evil nature and revels in reembracing it.<ref name="ten22" /> Despite this, Castiel is able to enlist Crowley's help in getting the ingredients needed for the spell to remove the Mark of Cain. However, after performing the spell, Rowena escapes and uses the Attack Dog Spell to force Castiel to kill Crowley.<ref name="ten23" /> Crowley escapes death by fleeing his [[meatsuit]] and then calling in demons to secure it once Castiel has left. Upon returning to his usual body, Crowley is informed by [[Jervis]] and another demon that [[Michael]], [[Lucifer]] or both rattled the Cage, putting Hell into an uproar because of the belief that one or both of the archangels was trying to warn them about [[the Darkness]].<ref name="eleven01" />
Following the death of Crowley, the last [[Prince of Hell]] [[Asmodeus]] takes control of Hell, proclaiming that he will return it to the old days of fire and brimstone.<ref name="thirteen02" /> Under Asmodeus' leadership, the demons actively hunt for the [[Nephilim]] [[Jack Kline]] and take Lucifer captive, though he later escapes with the aid of Castiel. Hell also begins preparing for a possible upcoming invasion by the [[Apocalypse World]] [[Michael (Apocalypse World)|Michael]].<ref name="thirteen07">[[13.07 War of the Worlds]]</ref><ref name="thirteen12" /> However, not all demons are willing to bow to Asmodeus' will and the [[Crossroads Demon]] [[Barthamus]] makes a deal with Sam and Dean to exchange a [[Nephilim]] tracking spell for their help in retrieving his human bones from [[Luther Shrike]]. Though they get the bones with the help of [[Alice]] and the demon [[Grab]], Grab is killed by Luther who reveals the truth about his history with Barthamus to the Winchesters. Disgusted, Sam and Dean refuse to complete the deal and Barthamus, who was also sought by Asmodeus for his rogue actions, is killed when Alice burns Barthamus' human bones.<ref name="thirteen08" />
