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In the Beginning

Castiel sends Dean back 1973 to meet his parents when they were young. The purpose of this was to show Dean the truth of what happened with Mary Winchester and Azazel. Castiel explains that the angels still have no idea what Azazels endgame is. He then tells Dean that Sam is headed down a dangerous road and that if Dean doesnt stop him, the angels will. 4.07 Its the Great Pumpkin, Sam Winchester. Dean and Sam return to their motel room to find Castiel and Uriel waiting. Sam is thrilled to meet Castiel. Castiels response is to acknowledge Sam as the "boy with the demon blood" and says that he is glad Sam is no longer using his powers. Castiel reveals they found a hex bag, which wouldve killed the boys, secreted in the room. He then tells them that the raising of Samhain by the witch will break another of the 66 Seals. He advises Sam and Dean to leave town because he and Uriel are going to destroy it. Sam and Dean argue that they can find and kill the witch and stop the summoning of Samhain. Later Uriel expresses his contempt for humans and tries to persuade Castiel that they should destroy the town anyway. Castiel reminds him that Dean was saved because he has "potential," and reminds Uriel that they must follow their "true orders." After Sam has used his powers to send Samhain to Hell, Castiel appears to Dean. He reveals that their true orders were to follow Deans decision, as a test under battlefield conditions. Dean, thinking hes failed, asserts that hed make the same decisions all over again if he had to, because of what he and Sam have saved. Castiel confides that he was praying Dean would choose as he did, and that he respects and loves humans as Gods creations. He also admits that he has doubts about the plan from Heaven, and is no longer sure what is right and what is wrong. He warns that in the coming months, there will be more hard decisions for Dean -- and the angel does not envy him that.