How does one traverse the spheres of the hidden, the obscure, or the enigmatic? How does one begin to track those secret societies, underground circles, or anonymous movements who use code-languages and ciphers to generate their subterranean worlds? To make such encounters possible, must we not exile thought itself to the domains of disorientation, puzzle, and dark curiosity? This talk will revolve around the formulation of a cryptographic imagination: that is, a certain anthropology of rumor, conspiracy, omen, camouflage, and mood which might unlock the many zones of encryption. From riddle languages and mystical alphabets to Books of Plague and Books of Sleep, from medieval catalogues of poisons or hallucinations to the futuristic image-generators of virtual reality cities, we will motion from surface to surface in search of a method to enter shadow.