|“||I have the next step. For Jack. (...) The first quest was meant to strengthen Jack's body. Step two is more spiritual in nature. (...) Jack needs to find the Occultum. (...) I don't know, it's hidden. Missing for centuries. Sacred, potent. (...) Not a weapon per se. But it's powerful. (...) So are you ready? Truly? (...) Good. Because we need to be ready and vigilant... and not stupid. God -- if he catches on to what we're doing, everything comes crashing down.||”|
|“||Cass went to the Empty. Hopefully. To find Ruby, hopefully, to find out where this Occultum thing is located. Hopefully.||”|
|“||His soul is back.||”|
After the Nephilim Jack Kline loses his soul, God returns to off the Winchesters a way to kill him in revenge for the death of Mary Winchester using the Equalizer, a gun created by Chuck himself. Having come to the conclusion that he is in fact a monster, Jack resigns himself to allowing Dean to kill him while Sam realizes that Chuck wants it for his perfect story and is counting upon Dean's desire for revenge. However, Dean refuses to kill Jack despite Chuck's promises to resurrect his mother in exchange and Team Free Will realizes that Chuck has only been using and manipulating them this whole time. With the Winchesters refusing to cooperate, Chuck smites Jack before Sam shoots Chuck in the shoulder with the Equalizer. Fed up, Chuck declares the story to be over and with a snap of his fingers, turns day into night and rips Hell open, throwing open every door in Hell in the process, including the door to Lucifer's Cage. However, the Winchesters manage to avert this Ghostpocalypse.
Although the Winchesters believe the threat to be over after the Ghostpocalypse, unbeknownst to them, God soon after begins planning his ultimate ending which involves the brothers ultimately killing each other. Weakened after being shot by Sam with the Equalizer, God is eventually able to heal the wound and depart the Earth after convincing Sam to give up on hope. God subsequently begins destroying the Multiverse.
Once God has left the Earth, Billie approaches Jack in the Empty and resurrects him to kill God. After completing the first step of Billie's plan by killing all of the surviving Grigori and consuming their hearts, Jack's resurrection is revealed to the Winchesters and Castiel and Jack tells them that he can become strong enough to kill God. Billie subsequently reveals that Chuck is destroying all other worlds and that according to Chuck's Death Book, Sam and Dean also have a role as the Messengers of God's Destruction.
As the Winchesters search through the Internet for any sign of God and the lore for anything useful, they hear a strange sound from another room in the Men of Letters bunker. In the armory, the Winchesters find a Fiat 500 with an open rift behind it and another, fancier dressed, Sam and Dean emerging from the car. As the four stare at each other in shock, the rift flickers and pulls both the alternate Winchesters and their car back in.
In the library, Sam and Dean inform a confused Castiel about the events that they had witnessed. As the three try to make sense of what happened, Billie appears and explains that the other Sam and Dean were running because God was destroying their reality. Billie warns them that God is almost done destroying the Multiverse and that when he's done, it's their turn and they must thus be prepared.
As Jack enters the room, Billie announces that she has the next step in the plan to kill God for him. Jack announces that he's ready and that he's feeling good about it. Billie explains that the first quest was meant to strengthen Jack's body while step two is more spiritual in nature. Castiel asks for Billie to be more specific and she states that Jack needs to find the Occultum. Sam recognizes that Occultum is Latin for hidden and asks where it is, but she admits that she doesn't as it's hidden, missing for centuries.
Billie states that the Occultum is sacred and potent and that while it's not a weapon per se, it is powerful, but she doesn't elaborate any more on the subject. Billie checks with Jack that he is truly ready which he confirms. Billie is pleased by this, telling the group that they need to be ready, vigilant and not stupid, pointedly reminding them of this last point due to their, to her, reckless recent rescue mission to the Bad Place using Jack's powers. Billie warns them that if God catches on to what they are doing, everything will come crashing down.
Looking through the lore, a frustrated Sam discovers that there is barely even a mention of the Occultum and nothing on where to find it. Sam wonders what the Occultum is even supposed to do and what it being "spiritual" means before noticing that Dean is distracted. Dean points out how crazy the current situation is and reminds Sam that even if Jack does kill God, that still leaves Amara. Dean suggests having Jack kill both God and Amara as killing just God throws everything out of balance which means that the world pretty much ends. However, if Jack kills Amara as well, the destruction of both God and the Darkness will keep things from falling out of balance and save the world. Sam wonders who will take over if that happens and if it will be Jack, but their conversation is interrupted by Jack entering and blowing bubble gum for the first time and Dean dismisses the idea. Sam and Dean ask Jack about any specifics for when he goes up against Chuck, but he doesn't have any answers about that.
Castiel enters, getting off of the phone and reveals that he has information on the Occultum from the shaman Sergei. According to Sergei, the Occultum is divine in its origin and it was housed for hundreds of years in an ancient temple with Dean adding in increasingly ridiculous guesses about what happened to it next before Castiel explains that it was looted by Mongol hordes for trade on the black market. Castiel states that until a few years ago, the Occultum was owned by the Jacobson family until Hyram Jacobson's son fell gravely ill and he was told nothing could be done. In desperation, Hyram had turned to a faith healer who saved the child but who would only accept the Occultum in payment. While they don't have a name for the faith healer, they do have a description: an attractive woman who healed the child by laying on hands which glowed. The Winchesters instantly realize that the faith healer was in fact the angel Anael who has been working for years as a faith healer in exchange for payment.
The Winchesters approach Anael and Dean suggests that some of her fortune comes from Hyram Jacobson suggesting her to his other rich friends, but Anael refuses to talk about that. Sam and Dean ask Anael about the Occultum, telling her that they need it to kill God. When Anael scoffs at the idea, Dean explains that the message that Anael and Castiel had tried had worked and that God is back, pissed and planning on murdering the world unless they stop him. Anael asks if they want her to be on their side against God which they confirm. Anael refuses to help, stating that she is not going to make God her enemy as he is God.
Drawing angel blades, the Winchesters inform Anael that she doesn't have a choice and challenge her to try them. Anael reveals that she doesn't have the Occultum, but an old friend of theirs does: the demon Ruby. Anael explains that she was on the road near Topeka when Ruby found her. Sam is surprised to hear that Anael and Ruby were friends, but Anael claims that they weren't, just that sometimes they'd pool their talents and run a job together if the opportunity presented itself.
In the past, Ruby accuses Anael of holding out on her while the angel claims that she respects their arrangement and doesn't butt in when someone wants their soul back and Ruby agrees to return it for a tidy fee while Ruby is good with Anael's "bleeding heart side-show." Ruby knows that the angel has the Occultum and states that she can get her a buyer for it in exchange for giving Ruby a taste. Ruby suggests that Anael would agree to it for money given just how much money that the Occultum is worth. With it being worth millions, Anael gave it to her and Ruby hid it until she could contact the buyer. However, Ruby never contacted the buyer because Dean killed her before Ruby could. Anael tells Sam and Dean that the Occultum was stashed by Ruby in Hell before her death.
In the bunker, Castiel finds Jack enjoying fast food, reminiscing on how different sensations are now that he's no longer dead. However, while Jack wants to be into such sensations, he no longer feels things the way that he used to due to being soulless. While Jack used to feel things deeply, he now understands such feelings, but he knows that they are no longer in him. Jack understands why Sam and Dean are angered by what he did to Mary Winchester and that it has caused them pain and that things have changed, especially with Dean. Jack wonders if Dean will ever forgive him and Castiel suggests that Dean might with time, but Castiel doesn't know how long that could take.
Sam and Dean return to the bunker and Sam is sure that he can use Rowena's Journals to perform the spell to get them into Hell again. As Castiel enters, Dean tells him that they sort of know where the Occultum is, but a concerned Castiel leads the Winchesters out of the room and into the armory where a ghostly projection of the alternate Sam and Dean is visible upon the wall. Castiel explains that the alternate Winchesters can't see or hear them and that if Chuck tried to destroy them as their world's rift was closing, the blast may have trapped them between dimensions.
With their alternate versions appearing confused rather than in pain, Dean decides to deal with it later as he and Sam have to go to Hell. Sam explains to the confused Castiel that Hell is where Anael told them that Ruby had stashed the Occultum. Castiel questions their trust in Anael and Dean points out how Anael had helped Castiel out. Castiel reminds them that Hell is a big place and states that they could be searching it forever and they need more information. Castiel suggests asking Ruby herself, but Dean points out that Ruby is dead and that they have to work with what they have. Dean states that they will go to Hell to search for the Occultum while Castiel stays on Earth in order to keep the spell alive so that they can get back.
Arriving in Hell, Sam and Dean quickly encounter a demon, Gregor, and ask him to see Rowena. Visibly annoyed, the demon tells them that Rowena is hosting a reception for newly-condemned souls and he agrees to take them to her.
On Earth, Castiel monitors the spell when Jack enters and confirms that the Winchesters made it into Hell. However, Castiel feels that there are too many holes in Anael's story such as who Ruby was going to sell the Occultum to and why Anael never tried to get it back. Castiel feels that the only way to get the answers is to ask Ruby herself despite Ruby being dead. Castiel tells Jack that he needs the young Nephilim's assistance: Castiel needs Jack to kill him, "almost." In theory, if Castiel is brought to death's brink, he should be able to put one foot into the afterlife and contact Ruby in the Empty itself. Jack reminds Castiel that the Shadow doesn't exactly like him, but Castiel feels that he should be fine even with their deal as he is far from happy.
Castiel tells Jack that he needs Jack to draw out most of his life force, store it in a flask that Castiel has retrieved and keep a close watch to pull him out in case it seems like Castiel really dying and not almost dying. Jack points out that even without a soul he knows that killing Castiel is wrong and expresses concerns about screwing up. While Castiel knows that he would be lost forever if that happens, he expresses confidence that Jack will do fine and informs him that he must also keep the spell going so that Sam and Dean can return from Hell or they'll be lost forever. Even though he isn't at all sure, Castiel instructs Jack to give him an hour before bringing him back from the Empty. Jack reluctantly uses his powers to draw most of Castiel's lifeforce out of his vessel and into the flask, leaving Castiel unresponsive in his chair.
In Hell, Gregor leads the Winchesters down a hallway while they become suspicious that it is starting to feel like a trap. Opening a door, Gregor reveals an empty room before he draws an angel blade and is joined by two other demons also armed with angel blades. Dean single-handedly fights the other two demons while Sam battles Gregor. Dean manages to kill his opponents while Sam, after initially struggling against Gregor, eventually manages to overpower and capture the demon.
Sam demands to know why Gregor was trying to kill them and he explains that he was ordered to and Dean asks if it was Rowena. However, Gregor reveals that it was Anael who hired them, promising to help the three demons escape from Hell if they killed the Winchesters for her. Sam asks why Anael wants them dead, but Gregor simply orders him to ask Anael himself. At a nod from Dean, Sam drives his angel blade into Gregor's abdomen, killing him. The Winchesters realize that Anael had set them up.
On Earth, Anael burns her flyers for her faith healing service and rolls up her banner. As a man shows up looking for her healing services, Anael tells him that "Sister Jo" retired and went to Florida. Before leaving, Anael offers him free advice to not make friends as they always ask too much of you.
In the Empty, Castiel searches for Ruby, calling out for the demon. Instead, Castiel is greeted by what appears to be Meg but is actually the Shadow using her form. As Castiel wants to see Ruby, the Shadow chose to go with the demon theme and use the form of Meg. Castiel questions where he can find Ruby and informs the Shadow that he is there fulfilling a request ordered by Death herself. Castiel knows that the Shadow and Billie are working together which the Shadow confirms, but states that it doesn't mean that it will help him. Castiel tells the Shadow that it does mean that it will help him and, annoyed that Castiel is no fun, the being tells him to go get her.
Nearby, a pulsing ball of light appears that transforms into Ruby in the form of her last vessel. Castiel informs the demon that she is dead which Ruby remembers and asks if he is also dead. Castiel admits that he is almost dead and that he woke Ruby up as he is looking for the Occultum which Anael told them that Ruby hid it somewhere in Hell. Ruby scoffs at this and points out how obvious it is for a demon to hide something in Hell. Castiel tells Ruby that Sam and Dean are searching in Hell now and Ruby reminisces upon her relationship with Sam and asks after him.
Not having much time, Castiel begins asking Ruby about when she went to Anael about the Occultum. Ruby reveals that Anael actually called her about the Occultum, not the other way around. In the past, an annoyed Ruby visits Anael who tells her that Lucifer and Michael are circling each other and a showdown is coming. Anael knows that Ruby thinks that she's in solid with Lucifer, but they both know that if the two archangels go at it, it will mean the Apocalypse which will leave nothing left standing. While Anael acknowledges that things could go Ruby's way, they might also go Heaven's at which point everyone will need a Plan B. Ruby and Anael work well together when they have to, a powerful demon and a good businesswoman. When the smoke clears, there will be a new world order and they can make that work for them. Although Ruby points out that Anael said that they would all be dead, Anael suggests that they wouldn't have to be if they ride out the Apocalypse in the safest place that exists: the Occultum.
In the Empty, Castiel is surprised to hear that the Occultum is a place. Ruby explains that it is "a place, a thing, a whatever you want to call it, but it's powerful." Anael and Ruby had cut a deal and Ruby stashed the Occultum. The demon offers to tell Castiel where she hid it which is not in Hell. Castiel asks if Anael knows where it is, but Ruby states that she never told the angel, knowing that she can't be trusted.
Ruby insists that Castiel can trust her and she will help him on the condition that Castiel get her out of the Empty. Ruby tells Castiel that the Empty is given its name because it's full of sorrow and despair playing over and over again, of angels and demons dreaming about their regrets forever which Castiel knows from his own experiences there. Ruby knows that Castiel is clearly connected and asks him to just try to get her out which Castiel agrees to do. Ruby whispers the Occultum's location in Castiel's ear before backing up and vanishing.
On Earth, Sam and Dean return from Hell to find Castiel mostly dead. Jack explains how Castiel went to the Empty to hopefully discover where the Occultum is from Ruby. Dean orders Jack to bring Castiel back immediately as he and Sam feel that there are too many hopefuls in the plan. Jack starts returning Castiel's lifeforce to him which takes an extended period of time.
In the Empty, Castiel is approached by the Shadow who, despite their deal, is unwilling to just let Castiel go. The Shadow begins causing Castiel great pain, stating that he is not dead yet and it can make him wish he was during the time that he is in the Empty. Castiel insists that the Shadow can't hurt him as they are on the same side against Chuck, but the Shadow tells him that it is on Death's side and that when her plan works, it finally gets to go back to sleep. Castiel is surprised to learn that Billie promised that and that she can do that. The Shadow tells Castiel that nowhere in Billie's plan did she ever mention needing him and sadistically continues torturing the Seraphim, stating that traipsing in and out of the Empty upsets the order of things. As the Shadow taunts Castiel, Jack finishes restoring his lifeforce and Castiel vanishes from the Empty. Unconcerned, the Shadow promises to see him soon.
On Earth, Castiel is pleased to see that the Winchesters made it back and Dean reprimands him for his actions. Castiel reveals that his plan worked and that the Occultum was never in Hell which the Winchesters already know. Castiel explains that the Occultum is apparently the safest place in the world which Anael was never going to give up. Dean is surprised to learn that the Occultum is a place and realizes that it means that Castiel saw Ruby. Castiel confirms this along with the fact that he got the location of the Occultum.
While Sam wants to leave immediately, Jack points out that if Chuck checks in on them and finds the Winchesters gone, it would all be over which Sam acknowledges. However, Dean comes up with a dumb idea. Leading the others to the armory, Dean explains that if Chuck comes back to check up on them, he will look for them in the bunker. As Chuck would need to see them there in the bunker, Dean's suggestion is to have their alternate reality selves pose as them in order to fool Chuck. Dean tells the others that they can try opening up a rift using the same ritual that they used to open up a rift to Apocalypse World. As their alternate selves are already halfway there, they don't need archangel grace and he believes that Castiel's grace will be enough. Although Sam points out that they could just be blasted away to another world, Dean figures that it's a better option than just leaving them trapped between worlds.
Sam performs the altered ritual and successfully pulls the alternate Sam and Dean into the Main Universe. The Winchesters explain to their counterparts how their world was destroyed by God and learn of their counterparts lives as part of a worldwide organization of hunters organized by their version of John Winchester. However, they don't know where John is now as they all went through the rift together but they got separated. Sam and Dean tell their counterparts that they plan to stop God from destroying the Main Universe as well, but God might check in on them in the bunker. Dean explains that in order to prevent that, the alternate Sam and Dean will remain behind in the bunker posing as them starting with their counterparts changing their appearances to match theirs, something that the alternate Sam and Dean aren't enthusiastic about.
While the others are gone, the alternate Sam and Dean dress up as their counterparts, although alternate Sam refuses to lose his man bun. The two drink beers and pretend to research on the computer and note the difference between their lives and the Main Universe Sam and Dean. The alternate Dean comes to the conclusion that compared to their more complicated lives, Sam and Dean have it made with their more mundane and simpler lifestyle.
The Winchesters, Castiel and Jack drive to the church that Ruby had given as the location in her very specific directions. Dean is suspicious as Anael's directions had also been specific and Jack points out how easy it all seems to be which Sam acknowledges. As Dean works on opening the doors, the group hears a growling noise in the nearby trees and Jack wonders if it's a bear. However, Sam and Castiel, who draws his angel blade, quickly realize that it's actually hellhounds. As the two hellhounds rush the group, Dean gets the door open and they rush inside of the church.
While Sam works to barricade the door, using a pair of handcuffs as a lock, Dean is annoyed by Ruby not mentioning the hellhounds that she had left to guard the Occultum. Castiel informs Jack and Dean that Ruby told him that the top of the cross would point the way, but looking at the church's cross, they don't see anything that it could be pointing to.
As Sam tries to hold the hellhounds at bay and Dean, Castiel and Jack look around, the moon comes out from behind the clouds and shines through one of the church's windows that has the form of a cross. The moonlight makes a cross pattern on the floor as a result which Jack notices and draws the attention of the other two to. Dean removes the floorboard that the top of the cross is pointing to and finds a bag with a small orb inside. Castiel discovers that the orb has an Enochian passage that, loosely translated, reads that "in order to be in the Occultum, the Occultum must be in you."
Jack takes the Occultum as Sam continues holding the door shut and Dean argues that Anael and Ruby are just trying to kill them. To Dean and Castiel's shock, Jack swallows the Occultum, taking the translation of the passage that it had to be inside of him literally. After insisting that it's fine, Jack suddenly doubles over in pain, begins glowing and vanishes in a flash of light.
Jack appears in a beautiful garden where a young girl approaches him and notes that Jack must not be human as humans may not enter and wonders if he's an angel. Jack simply states that it's a long story and asks why humans have to stay out. The girl tells him that they are in the Garden, man's beginning and Jack realizes that she means that they are in the Garden of Eden like with Adam and Eve. The girl explains that God had loved Adam and Eve, his prized creations, until he banished them and all of mankind from the perfection of the Garden before hiding it away. Jack asks about being told that the Garden might change him somehow which the girl confirms could happen if he was the one meant to find it and promises that Jack will know soon enough before walking away and vanishing.
In the church, Dean confronts Castiel over Jack vanishing, but the angel has no idea what's happening or that it would involve ingesting a magic sphere and disappearing. As they argue, the hellhounds get closer to breaking in despite Sam's best efforts.
In the Garden of Eden, Jack wanders around before the Snake appears behind him in a tree. The Snake questions who Jack is really and who he is meant to be. Falling to his knees, Jack is gripped with memories of his life as the Garden of Eden restores his lost soul. Gripped with remorse over the things he did while soulless, Jack collapses to the ground and immediately begins crying.
In the church, a ball of light appears and floats into the middle of the room. As the Winchesters and Castiel stare at it in confusion, the hellhounds finally break in through the doors despite Sam's best efforts. The ball of light releases waves of energy that render the hellhounds briefly visible before disintegrating them. When the light is gone, Sam, Dean and Castiel discover that it has transformed into Jack, lying on the church's floor, stunned by the experience.
With the situation resolved, Sam and Dean send their counterparts to a new life in Brazil where they can relax and enjoy themselves. However, they earn Dean's ire by revealing that they took the Impala for a joyride.
After the alternate Sam and Dean are gone, Castiel reveals that Jack's visit to the Garden of Eden -- the crossroads between divinity and humanity where no one has been since the Exile until now -- has changed him. Crying, Jack expresses remorse for the death of Mary Winchester and begs for forgiveness, having previously been unable to understand the pain that he had caused. To Sam and Dean's shock, Castiel reveals that Jack's soul has been restored.
After God returns to the Main Universe, Dean and Jack meet with Adam, the First Man and the true architect of the plan to kill God. Adam and the angel Serafina reveal that restoring Jack's soul was a part of the process to prepare him to become a bomb capable of killing both God and the Darkness.
As a result of its encounter with Castiel in the Empty, the Shadow loses faith in Billie's trustworthiness and later seeks her out in Death's Reading Room to demand answers. Seeking out Billie at the same time, Sam encounters the Shadow who reveals to him that Billie's ultimate goal in preparing Jack to kill God and Amara is for her to take power herself once they are gone and that Billie is just using everybody to her own ends.
- This battle marks the final time that the Winchesters ever come up against demons and hellhounds, although the Crossroad Demon Zack appears in Gimme Shelter.
- This conflict occurs at the same time as part of the Destruction of the Multiverse.