Rainwater collection has long been a staple of the aspirant sustainable city's toolkit. A multitude of successful pilot projects in industrialized cities throughout the world have shown the many advantages of on–site rainwater retention, infiltration, and utilization. The transition from specialized to mainstream, on the other hand, has been mainly elusive. In terms of unfavorable institutional settings and obstinate sociotechnical regimes, recent research has given significant reasons for such stymied transformations. However, the urban aspects of rainwater collecting have received little attention. We know relatively little about how the 'urban' influences, and is influenced by, rainwater management policies and practices, despite numerous case studies on rainwater harvesting in cities. To explain the dynamic connections between rainwater harvesting and the city, this article relies on recent contributions to transitions research from human geography and urban studies. It provides a long-term examination of the policies and initiatives undertaken to encourage rainwater harvesting in the city of Berlin, which was an early pioneer of such technology. The results of the study show a great deal of variation over the last 30 years, not only in terms of the tools used and plans created, but also in terms of political motivations and priorities. This is understood in terms of changing settings and contingent occurrences in (and beyond) Berlin, both geographically and chronologically. The article makes a case for a more nuanced view of how the 'urban' pervades sociotechnical changes in general, and rainwater management routes in particular.