Extending innovations from urban experiments to the wider urban area is often assumed to be relatively easy, as if they can simply be ‘rolled out’. In practice, however, extending innovations is usually constrained by a range of factors in the wider context of the innovation, typically a context of interconnected and ‘obdurate’ urban socio-technical networks and institutions and the risk of social exclusion. Innovation studies have used the notion of upscaling from experiments, especially in strategic niche management and transition management. However, these studies have focused more on niche internal dynamics and future visions, respectively, and much less on constraints in the present socio-institutional context. This paper drafts an approach to anticipate constraints on extending innovations from inclusive urban experiments, and discusses the results of action research in four European cities in which this approach was tested in mobility-related topics. After describing the approach based on a review of the literature of transition, social innovation, geography and science & technology studies, we discuss how the approach was tested in four different ways and contexts. Based on the lessons we draw from these experiments, we discuss the merits and points for improvements of what can be seen as guidelines to anticipate the extension of inclusive urban experiments with socio-technical innovations.