In 2020, in the new EU strategic horizon1 that is opening at present, the place should matter more than ever when it refers to territories that are envisaged from the Social Innovation paradigm (Moulaert2, Mulgan3 and Morgan4). Nevertheless, how will the suggested H2020 strategy based on Smart City and Communities5, contribute and implement the so‐called Social Innovation; facing realistic, economic and politic‐driven issues in an increasingly territorially heterogeneous EU current context? This article aims to shed some light on the Critical Social Innovation (CSI) challenges from a constructive position. KEY WORDS: Critical Social Innovation, Urban Experimental Governance, City‐Regions, EU, H2020, RIS3, Smart Cities, Territorial Development Strategies and Penta Helix