Processes of designing for systemic innovation for sustainable development (SD) through the lens of three long-term case studies are reported. All case studies, which originated from the SLIM (Social Learning for the Integrated Management and Sustainable Use of Water at Catchment Scale) Project, funded within the EU Fifth Framework Program (2001–2004), constitute inquiry pathways that are explored using a critical incident approach. The initial starting conditions for each inquiry pathway are compared; significant pathway dependencies are identified which foster the development of social learning processes locally, but constrain their uptake and embedding across the wider system of interest. In the first case study, in England & Wales, promising developments in the application of social learning approaches to river basin planning over an initial 3-year period were subsequently marginalised, only to resurface towards the end of the 10-year period of study. In the second, South African case study, significant spaces for social learning and innovation in integrated water resources management were opened up over a five year period but closed down again, primarily as the result of lack of policy support by national government. The third, Italian, case study was designed to assess options for adapting to climate change by opening up new learning spaces between researchers, stakeholders and policy makers. A case for investing in local level systemic innovation through social-learning praxis design approaches and in learning processes around well contextualised case-studies is supported. However, concomitant investment by policy makers in social learning as an alternative, but complementary, governance mechanism for systemic innovation for SD is needed.