Current debates in urban development display a rising awareness that several cities in Europe and the US must deal with challenges of long-term urban shrinkage. However, on an international scale it is still not clear if and how planning paradigms, planning systems, planning strategies and planning cultures are changing when shrinkage and decline are taking place. This paper investigates how planning is transformed in view of shrinking cities. For this purpose, the paper introduces four cities’ storylines framed by shrinkage. Particular focus lies on the question if and how dealing with decline and shrinkage led to changes in urban planning and brought about different planning styles.