A central promise of urban experiments (UEs) is to create sites for social learning. However, research on such learning in sustainability transitions still lacks conceptual clarity and empirical evidence. This article helps to close this gap by analyzing how social learning emerges from urban experimentation. It adopts a transactional understanding of learning induced by disruptions of everyday habits and distinguishes cognitive, normative, and relational learning processes. Further, the additional dimension of socio-material learning is derived to account for changes in understanding or interpreting material realities. These concepts serve an analytical framework for a case study of two transition experiments carried out as part of the transdisciplinary research project “Dresden – City of the Future.” The two UEs strive to initiate local sustainability transitions pertaining to participatory governance of urban districts and co-creation of a livable schoolyard. The empirical results illustrate how interventions by the two UEs induced learning in the sense of changes of cognitive understandings, norms, relations among people, as well as between people and their socio-material environments. The experiments encouraged individual and collective learning and in particular the formation of collective identities and interpretations of specific places. By comparing two UEs, we further show differences in learning regarding the actor groups, namely that the majority of learning processes in the first experiment dealt with bridging the gap between prevalent routines of the school community and novel habits introduced by the initiators of the experiment. Participants of the second experiment were socio-ecologically minded from the outset and therefore fewer learning processes took place in this regard.