This chapter focuses on how urban development relates to riverine flood risk. It begins with an overview of flooding and related riverine processes (e.g., sediment transport, floodplain formation, channel migration). It then presents the urban development and flood histories of Vienna (Austria) on the Danube and Calgary (Canada) on the Bow River, including the latter’s 2013 flood disaster. The cases are assessed and compared using the Urban Risk Dynamics framework. Vienna and Calgary demonstrate several key themes, including the “levee effect.” Each city’s relationship with the river has been one of technological control, intensifying over time. During periods of major population growth, flood protection investments are made that allow the city to expand into hazard lands. Once set in motion, the reliance on technology for flood protection becomes self-reinforcing, difficult to reverse as more of the city comes to depend on it. Over time, there is a loss of collective memory about flood risk. The role of government becomes increasingly important. Disaster events lead to learning and adaptation but do not fundamentally alter processes of urban development that give rise to risk.