The publication explores policy and planning approaches to urban shrinkage and population decline from Bilbao, Spain (2000-2015), Leipzig, Germany (2000-2015) and Zeeland, the Netherlands (2018-2020). Through the main method of interpretive policy analysis, causal and normative dimensions of the policy and planning approaches are determined. The conclusions from the different cases are reviewed in a cross-national comparative framework, based on policy benchmarking. As a result of the policy benchmarking, variants of the new planning concept of "Shrinking Smart" are defined, providing recommendations for overall policy approach under conditions of population decline, encompassing: the planning process for shrinking cities; a decision making mechanism with normative orientation; economic development and quality of life as a broader policy framework; spatial planning under conditions of urban shrinkage. The conclusions are complemented by critical reflection on growth orientation and its pervasiveness under conditions of shrinkage and population decline as well as with recommendations on particular instruments under each of the concept variants.