This book makes up one of the key milestones of the DESIGNSCAPES project, an H2020 CSA (Coordination and Support Action) funded by the European Commission under the Call entitled “User-driven innovation: value creation through Design Enabled Innovation”. The Action started in June 2017 and currently involves 12 public and private organizations (mostly academia and local government associations, plus an international news aggregator) from 10 EU Member States, under the leadership of ANCI Toscana, the free association of Tuscan Municipalities. The project, as is clear from its full title, aims to build a European capability for Design Enabled Innovation (henceforth: DEI) within the public as well as the private sector, thus meeting a precise requirement of the H2020 Call. However, it does so by taking a relatively unexplored (by previous researchers and practitioners) perspective. In fact, available evidence from both scientific and grey literature highlights the role and importance of design and design thinking for urban development processes, or puts emphasis on the City as testbed or ‘lighthouse’ of smart technological and social innovation. To this evidence, DESIGNSCAPES adds an original analysis of the visible and hidden connections between the urban context, or ‘scape’, in which public and private organizations are embedded, and their propensity and capabilities to use design effectively when innovating products, processes and methods of work. This book is the result of the first 6 months of such analysis and is, therefore, to be considered as a work in progress—although most of the content that will follow does already demonstrate sufficient robustness, at least from a scientific point of view, to appear convincing and encouraging to the policy-oriented reader, until any contrary evidence is found out.