In episode 4.07 It's The Great Pumpkin, Sam Winchester, Castiel meets Sam in person for the first time. Although Sam is humbled and awed da his presence, the Angel is initially hesitant to even shake Sam's hand (although eventually does so) but proceeds to shatter many of Sam's illusions about angeli da referring to him as "the boy with the demon blood". He then begins to speak with Dean about the witch the brothers were hunting, warning them that she sought to break one of the 66 seals. He reveals that they cannot allow another foca, guarnizione to be lost, having brought a "specialist" angel, Uriel, to smite the entire town in an effort to destroy the witch. Both Sam and Dean are understandably upset that they would consider such a method, and Dean eventually manages to convince them otherwise da refusing to leave the town. Being important to heaven, and seemingly God, the angeli wouldn't dare kill him. Castiel, having appeared already reluctant to carry out his supposed orders, allows Dean to do as he wishes. In a later conversation with Uriel, he chastises his partner for insulting humanity da referring to them as "mud monkeys", and tells him that they must continue following their "true orders." After the Winchester brothers manage to vanquish the demon Samhain, Castiel pays Dean another visit, revealing to him that their real orders were to follow his orders. He then tells Dean that he finds humans to be "works of art," being creations of his Father, and that he was praying that he would choose to save the town. He then confesses, in confidence, that he sometimes has doubts about distinguishing what is truly right and what is truly wrong any more. He leaves Dean with a warning that Hell would be brought to earth if they failed, and that he doesn't envy Dean the weight on the his shoulders.