Within the globalising trajectory of modernism, conservation, then environmental (EE) and now sustainability education (ESD) have each emerged as developing responses to risk produced by and in the modern state. Through adopting a long term process perspective, this paper narrates the emergence of situated learning perspectives and a developing re-orientation of EE at the start of the United Nations Decade of Education for Sustainable Development (UNDESD). We identified the need to examine ESD practice in responses to recent ESD consultations in 14 southern African countries, where a rhetorical marking was noted in discussions on ESD practices, particularly with regard to changing teaching and learning processes. The paper narrates how an interplay of review, research and practical engagement activities have all contributed to an extended critical review of learning interactions in environmental education in an attempt to provide useful perspective for educational activities within the UNDESD. We found that EE and ESD initiatives only acquired more substantive meaning and coherent orientation when examined within ongoing inquiries into situated learning, agency and risk reduction in contexts of poverty, vulnerability and risk, the key concern to us in this paper and the primary focus of the WEHAB (Water, Energy, Health, Agriculture and Biodiversity) sustainable development agenda in the region.