Because of urban brownfields’ inherent complexity related to their very nature, as well as their intermediate scale—the neighbourhood—regeneration projects are not a spontaneous process. Indeed, an urban brownfield regeneration project may encounter several issues, which can be obstacles, barriers, or resistance, that we classify in four types: sociocultural barriers, governance involved by the multiplication of actors, legal and regulatory constraints, and deterrent costs. While these issues contribute in turn to complexify brownfield regeneration projects, they are not insurmountable. Finally, to overcome urban brownfield regeneration projects’ complexities and issues, we argue that there is a need to implement real project dynamics. To this end, we provide four potential approaches to foster the creative development of tailored solutions.