Leipzig, Germany has been continuously shrinking since 1966, a phenomenon accelerated and transformed by the post-socialist transition since 1989. The term “perforated city” was created to describe a new era of cities characterized by simultaneous demographic decline and urban sprawl. Unlike other East German city authorities, such as Dresden’s, Leipzig’s decided to adapt to shrinkage and perforation at an early stage in an attempt to manage the shrinkage process and take advantage of change. City planners aimed to build the image of a dynamic, sustainable city serving as a model of urban shrinkage management. Three main axes can be identified in their planning strategy: preserving the architectural heritage, considered a trademark of the city, creating green spaces and open spaces to replace dilapidated housing estates, and supporting the creation of a micro-scale hierarchy of centres. In practice, these strategies were largely limited to a marketing campaign based on the traditional rhetoric of urban regeneration, as planners lacked the financial and legal tools to fully implement them. Some interventions lead to conflicts with land owners about land use and might further intensify social and spatial differentiations in a context of territorial competition and polarisation. This case study is based on empirical research, including interviews with actors involved in shrinkage management, and an analysis of statistical data. It concludes that Leipzig’s image-based strategy could be, like Maya’s veil, a decoy aimed at hiding lack of influence and financial power to achieve the aim of managed shrinkage.