The book explores the relationship between the shrinking process and architecture and urban design practices. Starting from a journey in former East Germany, six different scenes are explored in which plans, projects, and policies have dealt with shrinkage since the 1990s. The book is a sequence of scenes that reveals the main characteristics, dynamics, narratives, reasons and ambiguities of the shrinking cities’ transformations in the face of a long transition. The first scene concerns the demolition and transformation of social mass housing in Leinefelde-Worbis. The second scene deals with the temporary appropriation of abandoned buildings in Halle-Neustadt. The third scene, observed in Leipzig, shows the results of green space projects in urban voids. The scene of the fourth situation observes the extraordinary efforts to renaturise a mining territory in the Lausitz region. The fifth scene takes us to Hoyerswerda, where emigration and ageing process required a reduction and demolition in housing stock and social infrastructures. The border city of Görlitz, the sixth and last scene, deals with the repopulation policies that aim to attract retirees from the West.