CC BY 4.0Ragozino, Stefania2024-02-052024-02-0520182468-064810.24306/plnxt/50https://doi.org/10.24306/plnxt/50https://hdl.handle.net/20.500.14235/1334plaNext-Next Generation Planning Vol. 7 (2018): Planning and critical entrepreneurship 63-81Considering that a relevant challenge for social enterprises is to assess their social impacts, this paper approaches this issue by investigating cases that exemplify engagement in culture-led regeneration processes. Assuming the paradigm of ‘Complex Urban Landscape’ (CUL) as a holistic approach focused on the role of relationships, and conceiving the social enterprise as a hybrid organisation potentially affecting the urban context, the author presents a reflection on one of the most-used and much-debated social impact evaluation methods, the Social Return On Investment (SROI). The research deals with three main challenges: the difficulties in integrating cultural heritage as commons within urban planning and practices; the potential role of social enterprises to transmit cultural value through experiences of culture-led regeneration processes; and the exigencies of planning and developing social impact evaluation capable of critically observing and narrating the theory of change proposed by social enterprises.enopenaccessHistoric Urban Landscape (HUL)Complex Urban Landscape (CUL)social enterpriseSROIarticle63-81