Rooftop architecture reveals great potentialities in favoring a new interpretation of urban spaces and new ways of living the city. Thanks to the redefinition of the morpho-techno-typological characteristics of urban-fabric, the verticalization and concentration of the city and its skyline, rooftop architecture creates unexpected spaces in contemporary metropolis, encouraging the performance upgrade of buildings and introducing new functions. This leads to the growth of innovative social and collective models. At present, the process is compromised by a lack of consideration of the contextual frame and the ‘genius loci’, due to the absence of a regulation able to relate the quality of interventions to a landscape scale. This means missing an opportunity for rethinking urban regeneration.