|“||I just got news about Charlie and Ketch. Going after the execution squad... went sideways. They're the ones who got ambushed.||”|
|“||I've sent for an expert in these matters. No talking will be required. Good evening, Castiel! Welcome.||”|
|“||We've been studying you. Pure steel. I haven't seen many like you. But... but you have to understand that everyone has a breaking point. A point of pain. Particular, primitive fear maybe. But it's a nerve so... raw that your will doesn't exist to be factors. And then all your little secrets, they flow from your mind to mine... until your mind no longer exists.||”|
|“||Well, hello! You actually saving me? Its about bloody time!||”|
Months after the formation of the resistance, hunters Dean Winchester and Arthur Ketch arrived in Apocalypse World in search of Mary and Jack. During this time, they witnessed Charlie Bradbury being taken to the POW camp known as the Silo for interrogation and execution. As the Main Universe Charlie Bradbury was an old friend of Dean's, he insisted on liberating the Silo to save Charlie's life. Though the rescue mission was successful, Dean was forced to leave as the rift to the Main Universe was closing. Arthur chose to remain behind to continue the search for Mary and Jack and to help coordinate the resistance for Dean's inevitable return with reinforcements.
In order to capture Arthur and Charlie to torture for information, five angels used a mole inside the resistance to send Charlie a tip that an angel execution squad was going to kill a resistance prisoner. Having fallen for the trick, Arthur and Charlie headed out to stop the angels.
Three of the angels escorted a fourth member of their party, disguised as a resistance captive, to the supposed execution location. Along the way, the lead angel announced that the "prisoner" would be executed for high crimes against the realm and the archangel Michael. The group of angels were confronted by Arthur and Charlie wielding guns loaded with angel-killing bullets and pretended to surrender. As Charlie went to help the "prisoner," Arthur covered the other angels with his weapon. Charlie comforted the "prisoner," he suddenly drew an angel blade and held it to Charlie's throat, exposing his true identity as an angel. With Charlie as a hostage, the lead angel demanded that Arthur drop his gun and come with them. With no other choice, Arthur was forced to surrender to the angels.
That night, Bobby Singer got word of Arthur and Charlie's capture and informed Dean, Sam and Mary Winchester. Recognizing that Arthur and Charlie were set up, Sam had Bobby bring the hunter who told Arthur and Charlie about the supposed execution before them. Once the hunter was before them, the Winchesters demanded to know if he had told Arthur and Charlie about the execution squad. When the hunter confirmed that he had but had not been complicit in the ambush, Dean had the Seraphim Castiel cause the hunter great mental pain until he broke and told them what he knew about the plot.
The angels took Arthur and Charlie to an abandoned Gas-n-Sip where the lead angel began torturing them for information on the numbers of the resistance and where their base was located. However, Arthur refused to break under the torture and taunted the angel. The angel revealed that he called for an expert on torture to help as a vehicle pulled up with the expert: the alternate Castiel.
The alternate Castiel approached Charlie, taking great joy in explaining how he would break her and learn all of her secrets. As the alternate Castiel began to cause Charlie great anguish to the horror of Arthur, the angels were interrupted by the power going out. Realizing that something was wrong, the lead angel ordered his men to secure the area as the alternate Castiel stopped his torture. Outside, one of the angels found another angel dead on the ground before being telekinetically blasted to the ground by Jack and killed.
With the situation deteriorating, the alternate Castiel fled out one door as Mary, Dean and Sam burst in through the other. Mary and Sam engaged the two guarding angels in combat while Dean quickly killed the lead angel with an angel blade. After a brief struggle, Mary and Sam overpowered their opponents and killed them with angel blades.
Outside, the alternate Castiel attempted to flee in his vehicle, only to be attacked by the Main Universe Castiel. The Main Universe Castiel easily overpowered his counterpart and pinned him to the side of the vehicle with an angel blade to the alternate Castiel's throat. The alternate Castiel was fascinated that his counterpart was "more than one of us" but disgusted that he aligned himself with the humans. After Castiel told the alternate Castiel that he vastly preferred humans over angels, the alternate Castiel stated that the Main Universe Castiel wasn't better than him and that they were the same. Agreeing with the sentiment, Castiel stabbed the alternate Castiel with his angel blade, killing him.
With all of the enemy angels dead, the Winchesters released Arthur and Charlie and returned to the resistance base. Shortly afterwards, the resistance departed through the rift to the Main Universe.
- During this fight, Sam got his second angel kill while Mary got her first known angel kill. Aside from killing several angels alongside Arthur Ketch with angel-killing bullets during the Liberation of the Silo, this fight featured Dean's third kill of a regular angel by himself and his third regular angel kill with an angel blade.
- This fight featured the second time a character was killed by their counterpart after Kaia Nieves was killed by her counterpart from the Bad Place in Wayward Sisters. In this case, it was the Main Universe Castiel killing his Apocalypse World counterpart.
- After being rescued by Dean, Arthur Ketch comments on actually being saved by Dean, referring to the times Arthur has saved the Winchesters lives in War of the Worlds and Devil's Bargain.
- The main fight goes down at a Gas-n-Sip. Castiel worked at one when he was briefly human in Season 9's Heaven Can't Wait.
- It is unclear how the angel found dead outside was killed, but he was presumably stabbed by an angel blade. Also, the angel Jack fought was not killed on-screen, but would not have been left alive by Jack or the Winchesters in any case.
- The conflict occurs at the same time as part of the Exodus from Apocalypse World.