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For six weeks after Dean disappears, Sam searches for his brother without success, capturing and torturing the [[Crossroads Demon]] [[Dar]] for information after tricking [[Lester Morris]] into summoning her.<ref name="ten01">[[10.01 Black]]</ref><ref name="ten03" /> At the same time, Dean, now a [[Knight of Hell]] himself<ref name="ten05" /> and Crowley hit the road, partying with each other. Although Crowley expresses interest in Dean ruling Hell at his side, Dean refuses. To sate the [[Mark of Cain]]'s bloodlust, Crowley sends surviving Abaddon loyalists to attack Dean who easily dispatches them.<ref name="ten01" /> Crowley also sends Dean to fulfill Lester's deal, but Dean kills Lester instead. With Dean proving to be too uncontrollable even for Crowley, Crowley makes a deal with Sam to help Sam capture Dean in exchange for the First Blade. Sam is able to capture Dean<ref name="ten02">[[10.02 Reichenbach]]</ref> and attempts to perform the [[demon cure]] upon his brother. Though Dean breaks free, he is restrained by Castiel who was himself rescued by Crowley from an attack by [[Adina]]. Sam is able to complete the cure and turn Dean human again, though he retains the Mark of Cain.<ref name="ten03" />
Having regained control of Hell, Crowley executes surviving Abaddon loyalists, though his alliance with Dean and method of ruling leads one dissatisfied demon to commit suicide.<ref name="ten03" /> Due to soul numbers being down following the war with Abaddon, [[Raul]], [[Gerald]] and another demon open a brothel where patrons sell their souls in exchange for the services of the kidnapped prostitutes. After meeting [[Shaylene]], one of the prostitutes, the Winchesters learn of the operation and attempt to shut it down. However, the [[witch]] [[Rowena MacLeod]] finds the brothel first and kills Raul, causing Gerald to flee. Though disgusted by the operation, Crowley dispatches demons to capture Rowena and kill the surviving prostitutes who are recruited by Rowena to form a coven. The demon assassins are killed by the Winchesters, saving one of the rescued prostitutes, but a second team is able to capture Rowena thanks to the intervention of [[Cole Trenton]]. Crowley is shocked to recognize Rowena as his long-absent mother,<ref name="ten07" /> something that she subsequently uses to manipulate Crowley.<ref name="ten09" /><ref name="ten10" >[[10.10 The Hunter Games]]</ref><ref name="ten14" /> In particular, Crowley has his demons capture [[Olivette]], High Priestess of the [[Grand Coven]] so that Rowena can petition to freely perform magic again.<ref name="ten16" >[[10.16 Paint it Black]]</ref> Following a failed attempt by Rowena to directly assassinate Dean and then to have Crowley do it, Crowley kicks Rowena out for her attempts to manipulate him.<ref name="ten17" >[[10.17 Inside Man]]</ref>
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" />
