Poe's exploration of hypocrisy occurs on several levels. Montresor is the ultimate hypocrite in presenting himself to Fortunato as a friend when, in reality, he hates him. He seeks revenge, but the honorable and honest way of achieving it, in the context of the time and place, would be to challenge him to a duel, or at least confront him openly in a less violent manner. Instead, he feigns amiability and takes advantage of the drunken state Fortunato is in to surprise him and kill him when Fortunato has no chance to defend himself.

The setting in which this takes place is symbolic of a kind of collective hypocrisy of the establishment to which Poe alludes elsewhere as well. It is very possible that the vault in which Montresor carries out his plan contains the bones of victims of the Inquisition. In both “The Pit and the Pendulum” and “The Black Cat,” the religious hypocrisy of the past is a backdrop, in the one case specifically in the story itself, and in the other, a reenactment which the narrator alludes to when he walls up the body of his murdered wife as “the monks of the Inquisition” did their victims. The catacombs in “The Cask of Amontillado” are an emblem of the religious hypocrisy of Europe's past and, as such, are the perfect setting for Montresor's cruelty.