In Apocalypse World, Dean reluctantly works with Arthur Ketch to find Mary and Jack. To Dean's shock, he witnesses a group of angels holding the alternate reality version of his old friend Charlie Bradbury captive. Against Arthur's wishes, Dean launches a rescue mission for Charlie. Dean reveals that he still holds guilt over his Charlie's murder and Arthur agrees to help him. The pair rescue Charlie, who reveals that Mary and Jack are leading a resistance against Michael. Out of time before the rift closes, Dean returns to his Earth while Arthur remains behind in Apocalypse World to aid the resistance and coordinate for Dean's inevitable return with reinforcements. At the same time, Sam bella and Castiel attempt to help Gabriel, learning that he faked his death when Lucifer "killed" him in order to escape all responsibility again. Asmodeus eventually locates Gabriel and leads an attack on the bunker to recapture him. However, Gabriel recovers and kills Asmodeus who proves to be no match for the weakened archangel. Gabriel chooses to abscond from his responsibility once again and departs, leaving the Winchesters without Gabriel's power to fight Michael or his grace to reopen the door to Apocalypse World. At the same time, Lucifer struggles in his new role as the ruler of Heaven, ultimately alienating Anael with his behavior.