This chapter examines the case of Rotterdam as one of the most representative cities in the Randstad in dealing with water and adapting to the current challenges. The dynamics of the regional water system, which include groundwater and rainwater in combination with surface water in a lowland delta facing the North Sea, is crucial for the process of development and urbanisation of the Dutch polders. By creating the Waterstad area, Rotterdam took profit from its strategic position in the Randstad Delta. Van der Ham described eighth century period of time until the year 1000 as distinguished by ‘natural water management’, as nature ruled over culture. At the end of the nineteenth century, explosive urbanisation and technological prosperity put pressure on the polder cities. The manipulative era is marked by the introduction of the engine and electricity, which had an immense influence on the city and the water system.