Urban design is not only about making proposals for possible futures, but also about designing the processes and tools by which those futures can be imagined. After School Detroit—our strategy for reimagining Detroit’s vacant schools—is exactly that: a designed process and toolkit that empowers residents, policymakers, and developers to envision new, positive futures for historic vacant schools. The City of Detroit currently stewards a portfolio of over 60 vacant historic school properties. This challenging reality is the result of decades of population decline and municipal bankruptcy. Confronted with the economic, social, and environmental burdens of managing these properties, the City sought a comprehensive strategy for their disposition—an unprecedented project. Our team developed a multiscalar, multidisciplinary process to assess the schools, along with unique programming and reuse proposals for each property based on its condition, history, neighborhood, and market value. Our goal was to visualize structures, illustrating strategies for adaptive reuse, mixed-use programming, and development phasing (such as mothballing and deconstruction). The project exemplifies the evolving role of architects and urban designers as stewards of the built environment, creatively imagining futures for buildings that are already there.