Taking as a starting point a fundamental hypothesis that explores the possibility of considering the urban rurality as a platform for the experimentation of a new model of sustainability, this paper presents a critical analysis of a recent North-Italian rurban experience. This scientific goal will be pursued through the assessment of a pilot project carried out at the territorial level and of strategic action plans drawn by the local authorities of the Provincia of Milan and developed within the context of the Parco Agricolo Sud Milano. These experiences are examined, on the one hand, in terms of their interscalar socio-political impacts both at local and territorial scales, and on the other hand, of the increasing conceptual gap existing between the local sustainable activities and contemporary political discourse built on the principles of sustainable development.