This chapter explores challenges faced on urban road networks in adapting to the changing role of cities and urban areas and responding to a growing set of pressures and competing objectives. It examines the recent shift in focus for roads, away from providing a predominantly movement-based function to one focused on place and space, and discusses reasons behind this shift. Through examination of a number of case studies, including London and New York, the chapter then looks at the changing composition of urban road users and how this is forecast to change in the future. In doing so, it considers future challenges and opportunities this presents for policy makers in cities with specific focus on the role the road network plays in delivering wider social, environmental, economic and health outcomes. The chapter then looks at political issues associated with how roads are managed and used and the challenges and obstacles this presents for delivering major change. Specific case studies are explored, including examples of delivering major change on London’s roads to promote a shift in usage away from motorised vehicles, the political issues that were faced and how they were overcome. Finally, the chapter considers the role of data and technology and the opportunities this creates for addressing future challenges and opportunities, with implications for how roads are planned, designed and operated.