Taking on a historical lens, this paper traces the development of cybernetics and systems thinking back to the 1950s, when a group of interdisciplinary scholars converged to create a new theoretical model based on machines and systems for understanding matters of meaning, information, consciousness, and life. By presenting a genealogy of research in the landscape architecture discipline, the paper argues that landscape architects have been an important part of the development of cybernetics by materializing systems based on cybernetic principles in the environment through ecologically based landscape design. The landscape discipline has developed a design framework that provides transformative insights into understanding machine intelligence. The paper calls for a new paradigm of environmental engagement to understand matters of design and machine intelligence.