The paper presents some of the results of research carried out by the authors on the unbuilt spaces of small and medium-sized towns, which are characterised by demographic and economic fragility, as well as by critical issues caused by climatic, cultural, geomorphological and social changes. Among the transformative tendencies often underway in open urban spaces are either top-down, excessively generalist/standardised interventions, or bottom-up, exclusively specialised/customised actions. Thus, the need for a synergy between universal and user-centred vision emerges, which allows us to rethink the unbuilt space of the city in an integrated way, as a regulatory-enabling interface. A regulatory-enabling interface is a system of spaces able to bring the challenges of urban sustainability within a wider relational and connective declination between resources, spaces, inhabitants, cultures and forms of local production. This challenge appears to be particularly feasible in small and medium-sized cities, due to the small size of the settlements, the permanence of long-lasting relationships between collective space, individuals and society, and the socio-cultural conditions that favour adaptation processes.

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