|“||I want you to suffer. I want you to go back to... to your normal life and forget about this and forget about me and... and when you give yourself permission to be happy and let the sun shine on your face. That's when I'll come. That's when I'll come to drag you to nothing.||”|
Suffering from an unknown illness after his grace was stolen, Jack slowly became more weakened and coughed up blood and hid this from everyone.
Rowena is contacted and she determines that because Jack's grace is what holds his human and angel halves in balance, it is coming into conflict with each other, since his grace has been diminished causing his body to shut down progressively. Rowena determines the only way to revert that is for the Nephilim to recharge their grace. Later on, they return to the bunker after Castiel met a Shaman who possessed a vial of Gabriel's grace, which they intend to use to recharge Jack's to hasten his recovery. However, Jack's body rejects it and his condition worsens and it is determined he is dying.
Jack soon succumbs and dies with his soul ascending to Heaven, leaving his friends grief stricken. However, they start looking into ways to resurrect him.
After noticing something was amiss, Jack leaves his personal Heaven and is chased by a black ooze. Managing to elude, Jack arrives in the personal Heaven of his mother and tells her of what is coming after him and she hides him from the threat.
Very soon, Castiel is alerted of Heaven's distress calls and heads off to investigate the cause. Castiel finds several angels defeated and finding a traumatized Duma, learns that a lurking threat is present. Castiel permits his scared sister to accompany him to find Jack.
Discovering Jack's heaven deserted, they are visited by Naomi who reveals they are being attacked by The Empty. Naomi reminds Castiel of his time in the realm, while telling The Shadow has come to claim Jack and take him to its domain. She wants to give in to its demands as Castiel refuses before the shadow overwhelmed and possessed Naomi who tells Castiel and Duma to run.
The pair flee and go to Kelly's Heaven, where Jack is hiding with his mother before they are alerted by Castiel's arrival. Castiel informs him that he and the Winchesters are working bring Jack back to life, which is why he present as Jack is surprised he'll be brought back. to life. Castiel explains that they will need to use magic that draws on Jack's soul to heal him. After learning that it will use up a small piece of Jack's soul in the process, Kelly and Jack become worried, forcing Castiel to explain that if they don't act on this The Shadow will take Jack to The Empty because of his half-angel heritage. If Jack is alive again, the Shadow will leave Heaven and the angels alone.
However, Duma appears but she is revealed to be possessed by the shadow, it reveals its intentions of claiming Jack. This forces Castiel to attack but he is easily overpowered and beaten down as Kelly steps in to defend him but she is knocked aside as well. Seeing his mother in pain, Jack attempts to attack but is easily defeated as The Shadow prepares to claim him but Castiel offers it a deal his place for Jack.
The Shadow accepts Castiel's deal, but it decides to wait until Castiel was truly happy to collect on it since it wanted his end to be painful. After making the deal, the Shadow left Heaven and returned to the Empty, ending the threat.
Afterwards, the angels return to normal with no left over damage from the attack. A protesting Jack questions Castiel who states that he carried out his act out of love for him and is at peace with his choice. Jack then promises to keep Castiel's secret as Castiel receives word the spell is finished. Jack seemed hesitant to leave his mother but Kelly implored her son to live a full life and thanked him for letting her share a memory with him. With this, Jack returned to earth and read a spell that allowed his soul to return to his body, completing his resurrection.
As Castiel leaves, Naomi thanks him for saving Heaven and offers him a reward for his noble act. She promises to tell him the location of Alternate Michael, something Castiel passes onto the Winchesters who are unaware of his deal.
- As of this battle, all of Team Free Will have died and been resurrected.
- Castiel's sacrifice for Jack is similar to Mary Winchester defending her sons from the reaper Billie.
- Jack officially meets his mother.