Historically, design education was structured around projects as solvable within a foreseeable and knowable future. However, researchers operating in the landscape of transition design must contend with far less certain terrain. Challenges fall outside the scope of what has commonly been understood as the designer's purview. Transition projects do not fit within the customary rhythms of political, economic, and governmental systems; they often require replete and complex coordination between actors in different systems; they are directed towards social, cultural, and psychological change; the location of practice is a living system that offers no reliable set of inflection points. Considering practice-based transition design research, this article outlines approaches taken, discusses challenges of conducting research, and proposes key considerations to address in future work.[Abstracts in spanish and portuguese at pages 281-282] (*) Michael Arnold Mages is a researcher and PhD candidate at Carnegie Mellon University. He also runs a design consultancy specializing in strategically oriented design practice: research, communications analysis, and planning, and is a partner in a startup that helps organizations have difficult conversations facilitated using deliberative democracy practices. Clients include mid-sized regionally oriented businesses, startups, universities, and Fortune 100 companies. Michael has taught research-informed design practice to students in business, computer science, and fine arts at the University of Colorado, The University of Denver, and now, Carnegie Mellon University. Michael's research includes designing for high-stakes and difficult conversations, sustainability, and designing for experience. michaelam@cmu.edu (**) Dimeji Onafuwa is a researcher and Ph.D. candidate at Carnegie Mellon University. His work seeks to understand the impact of platforms on contributing to the commons. A practicebased interpretation is how Ostrom's design principles might serve as a basis for user experience on platforms. Dimeji's work on a research project exploring multi-stakeholder interactions around tenant/landlord decision-making led to his work on tenancy as a contribution to the commons. Recently, he has begun investigating the emergence of patterns from commoning acts. Before joining CMU, Dimeji ran a design studio for eight years. He currently works as a UX consultant and serves on local government and corporate boards.