Environment and sustainability education processes are often oriented to change and transformation, and frequently involve the emergence of new forms of human activity. However, not much is known about how such change emerges from the learning process, or "how" it contributes to the development of transformative agency in community contexts. The authors of this article present four cross-case perspectives of expansive learning and transformative agency development in community-based education in southern Africa, studying communities pursuing new activities that are more socially just and sustainable. The four cases of community learning and transformative agency focus on the following activities: (1) sustainable agriculture in Lesotho; (2) seed saving and rainwater harvesting in Zimbabwe; (3) community-based irrigation scheme management in Mozambique; and (4) biodiversity conservation co-management in South Africa. The case studies all draw on cultural-historical activity theory to guide learning and change processes, especially third-generation cultural-historical activity theory (CHAT), which emphasises expansive learning in collectives across interacting activity systems. CHAT researchers, such as the authors of this article, argue that expansive learning can lead to the emergence of transformative agency. The authors extend their transformative agency analysis to probe if and how expansive learning might also facilitate instances of "transgressing norms"--viewed here as embedded practices which need to be reframed and changed in order for sustainability to emerge.