Students in the graduate class, Visions of Sustainable Communities, worked alongside City staff and a public-oriented non-profit design firm to 1) engage Asheville residents in the City of Asheville’s Comprehensive Planning process, 2) interpret public comment for a contested City-owned property redevelopment design, and 3) to help develop a set of indicators related to sustainability in the City. Students drew on literature in sustainable community development, facilitation, leadership, city planning, history, communication, psychology, ecology, business, philosophy, and social justice. The messy work of applied inquiry-guided learning led to critical lessons learned, experience gained, and insights developed that will translate into more effective approaches for building more sustainable communities among sustainability professionals. Reflections on the course development, teaching, project management, and learning processes are explored.