This article delineates the notion of conjectural artworks—that is, ways of thinking and explaining formal and relational phenomena by visual means—and presents an appraisal and review of the use of such visual ways in the work of Chilean biologists and philosophers Humberto Maturana and Francisco Varela. Particularly, the article focuses on their recurrent uses of Cellular Automaton, that is, discrete, locally interacting, rule-based mathematical models, as conjectural artworks for understanding the concepts of autopoiesis, structural coupling, cognition and enaction: (i.e. Protobio (...) and Bittorio). Additionally, the article proposes a new model of conjectural artwork based on an extension of cellular automaton: random Boolean networks namely, binary systems with variable local connections. Such model, as it is argued, is useful to connect the theoretical frameworks by Maturana and Varela, especially structural coupling and enaction, with other relevant fields such as biosemiotics’ Umwelt-research and cognitive landscapes in neurodynamics, and to advance and explore the concepts of structurally coupled categorization and generalization. (shrink)