There is a rising cross-disciplinary tendency in the field of urban planning and public arts curating: the qualities of artwork that are designed to intervene or pop up appear to be in specific interest of the public and urban planning realm, and more often contemporary art is described as an engine accelerating social engagement and development or offering social care in an urban context. This position constitutes a debate on the role public arts is serving in urban regeneration. The crossover in the disciplines of urban planning and curatorial practice seem to blur the boundaries between the methods. Since regeneration has its outset in the urban planning and curatorial practice is rooted in art criticism, the positions traditionally serve different aims. In this chapter, I discuss how a critical curatorial practice can unfold in the context of urban regeneration through two curatorial cases: one in the former Tempelhof airfield in Berlin, and the other in Hackney Wick in East London. I argue that a critical curatorial practice can enable contextual awareness and the ability to navigate critically in the mixture of artistic, political, and economic agendas.