Michael baits a trap for Sam, Mary and Bobby Singer using a vampire he had purposefully let escape. In "Nihilism," Sam and Castiel manage to entice Michael utilizing a combination of a holy hearth cocktail and the angel cuffs. Sam is able to summon Jack for assist by means of a prayer and Jack attacks Michael, seriously injuring him. In the Season thirteen finale "Let the good Times Roll", Michael unexpectedly attacks the Winchesters in a gasoline station near their bunker, having arrived in their world with Lucifer. Billie later visits Dean and warns him that every one variations of Dean's destiny however one has Michael escaping and using Dean's physique to destroy the world. Despite this, Michael retains his superior fighting expertise and warns that Dean will likely be burnt out if he kicked out of Dean's body. Following an assault by three more of Michael's monsters, Kaia departs with the spear even supposing Michael will never stop hunting her as long as she has it.

In response, the three group up together to lure Michael within the bar cooler, successfully trapping Michael in Dean's thoughts. After Dean is reminded of the truth, Michael seems within the bar and taunts Dean over him supposedly seeing Sam and Castiel as burdens. Before Jack can kill Michael, Lucifer's evil deeds are revealed to his son and Lucifer steals Jack's grace and departs with Jack and Sam. Because the war continues, Michael compels the Prophet Kevin Tran to commit a suicide bombing in opposition to the resistance in a somewhat profitable effort to interrupt Jack's spirit by exhibiting Jack that he can't save everybody. Seeing the state of Apocalypse World, Mary and Jack type a resistance in opposition to Michael with the intention of killing him to avoid wasting both worlds. In the penultimate episode of Season 13 "Exodus", the Winchesters return to Apocalypse World with Lucifer and Gabriel in an effort to lastly rescue Mary and Jack.

Gabriel's sacrifice permits the Winchesters to flee, leaving Michael caught in Apocalypse World with Lucifer when the rift closes moments earlier than Michael can attain it. However, Michael himself interrupts the exodus, hoping to preventing their escape and use the rift to succeed in their world. In "Ouroboros," Dean is knocked unconscious by a Gorgon during a hunt, allowing Michael to escape from his prison. Though Dean intends to be Michael's cage, he continues to work to interrupt free while his military disbands without Michael able to manage them. With Michael acknowledging that by working collectively, he and Dean would have a chance towards Lucifer, Dean provides Michael a deal where he will grow to be Michael's vessel to combat Lucifer, however Dean will stay in management whereas Michael powers him. The djinn explains that Michael, while nonetheless in Dean's physique, had ordered him to set himself up someplace quiet and act as a lure for hunters. However, they notice that Michael is simply stalling and is powerless in Dean's mind. However, Michael merely summons monsters to rescue him.

Michael is chained to a put up but summons his army to rescue him and works to instill doubts in Jack and Castiel over Dean's relationship with them. Michael reveals that after studying about God from Dean's mind, he has come to believe that God considers each worlds "failed drafts" and has left to start out again. In an try to cease Michael, Sam and Castiel use the British Men of Letters mind-link gadget to enter Dean's thoughts to attempt to get him to throw Michael out, locating Dean in a world Michael has created for him where Dean is completely pleased. With Lucifer dead, Michael betrays his deal with Dean, takes full control of his body and departs, free upon the Winchesters' world in his true vessel. In Season 14's "Stranger in a wierd Land," three weeks after possessing Dean, Michael travels around asking varied people and beings "what would you like?" while attempting to determine the answer with reference to himself. Within the Funtime Adventures episode Draw or Die, Pat mentions that anything could be within the void him and Matt fall into, including "mummified lobsters." Three guesses as to what ambushes them at the tip of the video.