In order to kill the Knight of Hell Abaddon, hunter Dean Winchester consented to becoming the bearer of the Mark of Cain. Due to the Mark's influence starting to transform Dean into a rage-fueled monster, his brother Sam began undertaking an effort to remove the Mark of Cain from Dean's arm. Ultimately, using the Book of the Damned, witch Rowena MacLeod was able to perform a spell that removed the Mark of Cain from Dean's arm. However, as a result, the Darkness was released into the world once more.
After receiving a series of visions from what he believed to be God, Sam undertook an effort to speak to Lucifer in hopes that Lucifer would know something that could defeat the Darkness. Unknown to Sam, Lucifer had sent the visions instead of God in order to lure Sam to Lucifer's Cage so that Lucifer could escape. While Sam ultimately refused to say "yes", Castiel consented to possession and became Lucifer's vessel. In the form of Castiel, Lucifer regained control of Hell and turned Crowley into his "dog."
In an attempt to defeat the Darkness, the Winchesters sought the help of what they believed to be Castiel to reach a Hand of God in 1943. Lucifer's disguise as Castiel was revealed and he was banished from the Men of Letters bunker, but not before it was determined that the Hand of God's power was depleted. Lucifer then began utilizing the resources of Hell to locate another and became convinced that Crowley may know something useful. As a result, he concocted a plan where he would allow Crowley to escape with the help of Simmons, in reality still loyal to Lucifer, in hopes that Crowley would lead him to another Hand of God.
As planned, Simmons approaches Crowley in his cage with the keys and tells him that she is helping Crowley to escape. Simmons claims that there are still demons that want Crowley back and the Devil should be afraid of Crowley, not the other way around. Simmons is eventually able to convince Crowley to make a break for it.
As the two make their way out, they are confronted by two demons. Crowley claims that Simmons made him escape before shoving her into one of the demons. As the other goes at him with an angel blade, Crowley grabs the demon's hand and uses it to shove the demon's own angel blade into him, killing the demon. He then quickly kills the other demon with the angel blade, impressing Simmons. Once they are away from Crowley's former lair, Crowley puts back on his usual suit and tells Simmons that they will now find "the ace up my sleeve."
Crowley leads Simmons to his lockup where he keeps the Rod of Aaron. Crowley tells Simmons he always knew the Rod was powerful but never before realized that it was a Hand of God. At that moment, Lucifer arrives, having followed them since Crowley's escape. Lucifer reveals that he set up a double-cross with the help of Simmons who hates Crowley along with the rest of Hell. Lucifer tells Crowley that Crowley may have once been the biggest evil aside from Lucifer himself, but he is now just "Dean Winchester's number one fan." Lucifer reveals that he knew Crowley was hiding something from him, but rather than beating it out of Crowley, he tricked Crowley into leading him to what he was hiding.
Taunting Crowley, Lucifer opens the box, only to find it empty. Crowley reveals he has the Rod of Aaron, having anticipated Lucifer's move and planned a double-cross of his own. Crowley hits Lucifer with the Rod, knocking him into hallway before absorbing the power of the Hand of God. Crowley uses the power he absorbed to fire a blast at Lucifer in an attempt to kill him, but Simmons jumps in front of the blast and explodes into dust with the force of the blast flinging Lucifer into the wall.
As Lucifer rises, Crowley attempts to blast him a second time, only to find that he has expended the power of the Rod of Aaron. Lucifer knocks Crowley over a table and realizing he can't win, Crowley teleports away to Lucifer's anger.
Following Crowley's escape, Lucifer sets his demons to hunting him while Crowley searches for another Hand of God and a way to lock Lucifer away again. After finding the Horn of Joshua, Crowley teams up with the Winchesters in a failed attempt to get Lucifer out of Castiel and use the Horn on the Darkness which results in Lucifer being captured by the Darkness.
- The nightclub Crowley changes back into his regular suit at, the Black Rose, is the same one from Live Free or Twihard that Boris's nest used as a hunting ground and where Dean was changed into a vampire.