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Rowena reunites with Crowley and makes several attempts to manipulate him for her own ends. Crowley is aware of Rowena's manipulations yet captures the head of the Grand Coven, [[Olivette]], for her. Under torture by Rowena, Olivette reveals the Grand Coven is now much diminished in its power.
Frustrated by Crowley's continued dealings with the Winchester brothers, Rowena attempts to drive a wedge between them. When this fails, she leaves Hell. Sam tracks her down and Sam entreats beseeches her help in decoding the ''[[Book of the Damned]]'' in the hope it will to reveal how to remove the [[Mark of Cain]] from Dean. Rowena agrees to help on the condition that Sam kill Crowley for her. Sam eventually holds her captive so she cannot escape while she decodes the ''[[Book of the Damned]].'
Following his failure to kill Crowley, Rowena determines the ingredients needed for the Mark-removal spell which involves her sacrificing the person she loves most in the world. Castiel is able to determine it is a young man named [[Oskar]] whose family had helped her hundreds of years ago, and of whom she was so fond that she cured him of a terminal disease and rendered him immortal. Castiel summons Crowley who brings them the ingredients as well as Oskar. Rowena kills Oskar and casts the spell to remove the Mark. The spell releases The Darkness at the same time. Rowena takes the opportunity to escape with the Book of the Damned and the codex, casting an Attack Dog Spell on Castiel so he will kill Crowley.
