In the face of climate change and the ecological transition, adaptability is increasingly viewed as a fundamental feature allowing urban environments to endure. This study focuses on the adaptation of the built environment and, by building upon the complex interpretation of cities, it intends to investigate how different governance configurations influenced the actors’ decisions and their interplay, thereby affecting the adaptation process. Following the distinction between top-down and bottom-up adaptation efforts, the paper adopts a historical perspective and analyses the role played by technological and normative constraints in determining the responsibilities of centralised and decentralised actors in modern and premodern urban contexts. The analysis shows that the societal transformation triggered by industrialisation translated into normative and technological constraints that increased the responsibilities of centralised actors such as public institutions, leaving aside more fine-grained adaptations driven by inhabitants and smaller parties. These findings underscore how decreasing decentralisation in decision-making affected urban adaptability and suggest that the distinctive governance configurations that used to characterise premodern cities could inspire policies fostering bottom-up adaptation processes.