In Chapter 6 the authors discuss the challenge of conducting evaluations of urban planning and spatial development from a gender+ perspective. Such evaluations are challenging because planning policies and systems vary from one country to another and the selection of an appropriate evaluation approach among the bewildering diversity of options on offer is far from self-evident. The chapter presents methodological results of gendered evaluations of two cases in the context of self-organisation around spatial development in Helsinki, Finland. The authors argue that the complexity of engendering evaluations of urban planning requires an integrated evaluation framework (gender studies, planning literature, feminist/gender evaluation approaches) and the application of mixed methods in order to facilitate knowledge building and to activate “learning to learn” behaviours around urban issues. The results furthermore revealed that evaluations are conditioned by context which in turn underscores the need for a well-tailored, integrative approach in order to tap the implicit ways of doing gender+. Raising awareness and knowledge concerning the quality, equity and justice of the urban and spatial environment are vital.