The Murders of Akobel and May was the conflict surrounding a jealous Ishim's attempt to get revenge upon Lily Sunder by murdering her angel husband and her daughter under the guise of May being a Nephilim.
All of her life, Lily Sunder dreams about and is fascinated by angels. Lily studies angels and their ways, ultimately finding a spell that allows her to summon an angel. The angel she summons is Ishim, the leader of an angel garrison. Ishim becomes obsessed with Lily, teaching her the secrets of angels, including about Enochian magic.
As time goes on, Lily recognizes that Ishim is obsessed with her and is a monster. In response, Lily breaks off contact with Ishim and eventually marries the Seraphim Akobel for the protection of herself and her daughter May.
Learning of Lily marrying the Seraphim Akobel, Ishim grows vengeful. In order to hurt Lily as he feels that she has hurt him, Ishim gathers his garrison under the lie that May is a Nephilim, an abomination in Heaven's eyes that must be eliminated.
Ishim brings his garrison to Orono, Maine where the Sunder Family is living in 1901. Outside of the Sunder home, Ishim tells Mirabel, Benjamin and Castiel, three prominent members of his garrison, his lie about May being the Nephilim daughter of Lily and Akobel. While Benjamin balks at killing at a kid, Mirabel and Castiel recognize the threat that a Nephilim poses with Ishim claiming that they are there "to set things right."
Joined by the other two members of their garrison, the three approach the house where, hearing them coming, Akobel and Lily emerge to face them. Akobel orders Lily back inside and whispers in her ear to "take May. Run." Lily reluctantly retreats into the house in an attempt to flee with her daughter.
Akobel confronts Ishim, telling Ishim that he has no business there. Ishim reminds Akobel that he was meant to observe humanity, not "taking up with a filthy animal." Akobel points out the hypocrisy of Ishim lecturing him on shame and delivers a speech about the merits of humanity. "How could anyone know them and not love them?" Akobel wonders.
Stating that he knows why Ishim is there, Akobel draws his angel blade and attempts to kill Ishim. However, Castiel blocks the blow with an angel blade of her own and Akobel is disarmed and restrained by Benjamin and Mirabel. On Ishim's command, Castiel recites "Akobel, Seraphim of the Sixth Choir. You have lain with a human and you fathered a Nephilim." Akobel expresses shock at this accusation, causing Ishim to strangle Akobel into silence so that Akobel won't reveal the truth to the other angels.
Continuing, Castiel tells Akobel that the penalty for him breaking their most sacred oath is death. Taking her cue, Mirabel stabs Akobel in the chest with an angel blade, killing him. Ishim tells his flight to dispose of Akobel's vessel while he'll deal with the Nephilim alone.
As Lily desperately tries to gather her things and keep her daughter calm, she hears the sound of Akobel's murder. A horrified Lily asks what Ishim has done, but he is unrepentant, telling Lily that he shared all of the angels secrets with her and loved her, but she left him for Akobel. Lily believes that Ishim never loved her, that he was just obsessed with her. Lily tells Ishim that she never should've let him into her life and that she had needed Akobel to protect her from him.
After Ishim states that "that didn't work well, did it," Lily realizes that he has killed Akobel and asks if he intends to kill her next. "No. You broke my heart Lily. Now I'm gonna break yours." Ishim telekinetically pins Lily to the kitchen table while pulling May to him and taunting Lily that she is powerless to do anything to stop him. As Lily desperately screams for Ishim to spare May, Ishim murders the little girl with his angel blade.
After murdering Akobel and May, Ishim leaves Lily alive to suffer the losses of her husband and daughter. Ishim claims to the other angels that he took pity on Lily and left her alive for that reason.
The murders of her husband and daughter drive Lily vengeful and uses her studies of Enochian magic to make herself immortal. For over a hundred years, Lily plots to get revenge against Ishim and his garrison and finally seizes her chance when the Fall of the Angels renders the angels more vulnerable as they no longer have their wings. Over the course of two years, Lily kills two unidentified angels, Benjamin and Mirabel. However, her attempt to kill Ishim and Castiel bring her into conflict with hunters Sam and Dean Winchester who are friends with Castiel. The Winchesters eventually learn the truth about Ishim from Lily and help her battle him. In the end, Castiel kills Ishim to save Lily's life, having learned the truth as well and Lily gets her revenge. Though Lily is unsure if she can forgive Castiel or not, he apologizes and offers that if she ever wants revenge upon him, she can come back and take it.
After getting her revenge, Lily gives up on her Enochian magic in order to preserve what is left of her soul. As a result, she begins to age and by late 2018, has become an old woman. Following the death of the Nephilim Jack, Lily is enlisted by the Winchesters and Castiel to help to save him. Lily helps to resurrect Jack before dying of a heart attack. In the afterlife, Lily is determined to be worthy of Heaven by Anubis and is allowed to finally be reunited with her daughter.
- During this conflict, Castiel is in a previously unknown female vessel. Castiel is typically seen in a male vessel.