In the era of climate change and increasing vulnerabilities, the ‘renewable’ choice has become a commonly accepted strategy to promote resilient and sustainable solutions. The intensive activities of the industrialized era of the past century brought disused and derelict land amidst chances and ambiguous issues on their management. Although research on regeneration projects is active, integrated and theoretically grounded approaches are still under exploration. From this spectrum, this work handles the compelling transition on ‘solar energy farms’ (the so-called ‘brightfields’) through a qualitative and multiple case study analysis. This research fills a gap where there is otherwise very little on the subject of ‘brightfields’ as an alternative form of land use management, a persistent problem of urban settings providing an in-depth description of the phenomenon towards a strategy beyond current literature. Key issues of questioning the brownfields’ transformation through a case analysis of the barriers and opportunities of the ‘brightfield’ strategy are provided. Further research is expected to result in supporting tools enabling progress in more sites around the world.