This paper gives a critical view on the incredible growth of Shanghai since the millennium. It focuses on the search for a new identity by this metropolis, both in its new town development as well as on the transformation and regeneration of downtown areas. By explaining the most important planning policies and trends with the help of recent key projects, and analysing how these projects developed over time, the context and challenges of Shanghai’s rapid urban transformation become clearer. Especially the challenges for urban preservation and quest for an identity in this continuously changing urban landscape will become more insightful. Based on these insights recommendations are given on how Shanghai can be exemplary, within China and internationally in terms of urban development, urban regeneration, and becoming a more future-proof city. The paper concludes with some trends and future perspectives.