Virtual design production demands that information be increasingly encoded and decoded with image compression technologies. Since the Renaissance, the discourses of language and drawing and their actuation by the classical disciplinary treatise have been fundamental to the production of knowledge within the building arts. These early forms of data compression provoke reflection on theory and technology as critical counterparts to perception and imagination unique to the discipline of architecture. This research examines the illustrated expositions of Sebastiano Serlio through the lens of artificial intelligence (AI). The mimetic powers of technological data storage and retrieval and Serlio’s coded operations of orthographic projection drawing disclose other aesthetic and formal logics for architecture and its image that exist outside human perception. Examination of aesthetic communication theory provides a conceptual dimension of how architecture and artificial intelligent systems integrate both analog and digital modes of information processing. Tools and methods are reconsidered to propose alternative AI workflows that complicate normative and predictable linear design processes. The operative model presented demonstrates how augmenting and interpreting layered generative adversarial networks drive an integrated parametric process of three-dimensionalization. Concluding remarks contemplate the role of human design agency within these emerging modes of creative digital production.