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As Sam is preparing to kill Lilith, Zachariah holds Dean in the [[Green Room]] and finally explains that the Angels actually want [[Lucifer]] freed so that Michael can kill him. After Dean pleads and begs for help, Castiel helps him by temporarily banishing Zachariah and teleporting Dean so that he can stop Sam from killing Lilith, as her death is the last seal. Sam ultimately kills Lilith and releases Lucifer, which triggers the [[Apocalypse]].<ref name="four22">[[4.22 Lucifer Rising]]</ref>
[[image:Caszach.Jpg|300px|right|thumb|Zachariah alongside of Castiel.]]
Soon after the breaking of [[The 66 Seals]] and [[Archangel Lucifer]]'s release from the Cage, Zachariah and two angel assistants approach Dean and Sam at Chuck's house in Kripke's Hollow. Zachariah demands that Dean come with them, but Dean activates an [[Angel Banishing Sigil|angel banishing sigil]], which sends the angels away temporarily. Zachariah later uses Chuck and lures the Winchester brothers to their father's lock-up in up state New York where he reveals to Dean that he is [[Archangel Michael]]'s Sword wherein he is the true vessel but Dean must first consent to possession. After denying angelic-possession by Michael, Zachariah starts torturing Dean and Sam, but Castiel mysteriously returns from the dead and orders his superior away. He inscribes angelic runes into Sam and Dean's ribs which will hide them all angels, including Lucifer and himself.<ref name="five01">[[5.01 Sympathy for the Devil]]</ref>
===[[4.18 The Monster at the End of This Book]]===
Following Sam's confrontation with Lilith and the arrival of Chuck's archangel, Zachariah appears to Chuck Shurley after he has another vision. While it is not revealed what Chuck saw, he wants to warn Sam and Dean, but Zachariah tells him not to. Chuck threatens to kill himself, but Zachariah says they will only bring him back to life. In despair, Chuck asks what he should do. Zachariah replies "Do what you always do. Write."
===[[4.22 Lucifer Rising]]===