After opening a rift between the Main Universe and Apocalypse World in an effort to rescue his mother and the Nephilim Jack, Dean traveled through with Arthur Ketch. Shortly after arriving in a snowy forest, the two men witnessed the execution of two prisoners on a bridge by several angels and the discovery of Charlie Bradbury amongst them. Recognizing Charlie as a high-ranking member of the resistance, the commander ordered Charlie taken to the nearby POW camp for interrogation. Ultimately, Charlie didn't break under torture and the commander decided to execute her instead.
Having witnessed the events on the bridge, Dean insisted upon leading a rescue mission for Charlie. After being attacked by a bounty hunter, Dean was able to learn the location of the Silo and its purpose as a prisoner of war camp. Along with Charlie being a high-ranking member of the resistance who had met Mary and Jack, Dean still felt guilt for the murder of his own Charlie Bradbury. Hoping to redeem some of his own sins, Arthur agreed to help Dean attack the camp.
Following the bounty hunter's directions, the two hunters were able to locate the Silo as the commander brought out a dozen prisoners to witness the execution of Charlie Bradbury. Arming themselves with guns loaded with angel-killing bullets taken from the bounty hunter, the two men positioned themselves along the camp fence to watch for the right moment to strike.
As the executioner prepared to decaptiate Charlie, Dean threw a grenade at the angel. The blast knocked the angel to the ground, saving Charlie's life. Taking advantage of the confusion caused by the blast, several of the prisoners made a run for it. Charging into the camp, Dean and Arthur opened fire, killing the executioner and several other angels. As his men fell around him, the commander ducked into a building, barely missing being hit by a shot fired at him by Dean. The commander quickly teleported away as Dean freed Charlie and Arthur killed the remaining angels, allowing all of the prisoners to escape.
With the camp liberated, Dean and Arthur Ketch returned to the rift between the worlds with Charlie, explaining their mission to her along the way. Initially skeptical, Charlie was convinced by the appearance of the rift and revealed in the process that last she knew, Jack and Mary were creating an outpost in Dayton, Ohio.
With the rift rapidly closing, Arthur chose to remain in Apocalypse World to locate Mary and Jack and help the resistance coordinate for Dean's inevitable return with reinforcements. Charlie chose to stay as well and as Dean departed, joined Arthur in combating the returned commander and three more angels.