This article posits that resiliency and adaptation in landscape architecture studio projects must plan for changes and feedback loops. With this premise in mind, the article evaluates a landscape architecture design studio focused on designing and planning adaptive landscapes that are part of the Los Angeles River and its surrounding neighborhoods. Students were charged with planning for change over time and designing multiple scenarios that assume various forms and vagaries in management, care, environmental conditions, and policies, while also connecting to community needs. Their designs were guides that envisioned a range of possibilities—feedback loops creating environmental and social resiliencies that provide value over time. The studio and this article build on Joan Woodward’s (2008) work suggesting several shifts in landscape design practice for progressing toward resilient landscapes that accommodate surprise and disruption. The case study methods evaluating the studio approach included external and internal reviews of students’ work, student written reflections regarding the course, and instructors’ reflections on the work. Some reviewers felt the paucity of final state perspective renderings in some students’ work equated to diminished design rigor. Some students pushed back on the studio’s interdisciplinary scope, but others looked beyond fixed design solutions, giving entire systems deep consideration by considering how to provide economic resiliency toolkits and adopt best practices that could unfold and adapt over time based on a particular neighborhood’s needs and desires. Overall, the studio serves as a model for teaching that advances Woodward’s concepts and promotes her goal of seeing design as an infinite rather than finite game (Carse, 1986; Woodward, 2008).