This paper hypothesizes the future of Saskatchewan power production based on the theory of transition management. Power generation law and policy in Saskatchewan over the last century to the present is analyzed as a key component of a socio-technical regime. Understanding the legacy of law and policy is important given sustainability concerns and the realization that significant changes will be required in trajectories of development putting less strain on natural capital and ecosystem services. This paper examines the critical relationship between governance strategies at the macro socio and political landscape level and the particular policy mix that is found in the socio-technical regime of power generation in Saskatchewan. This exercise is informed by transition management theory and also the alternative explanations of path dependency. Switch points critical to the trajectory of power generation development are identified and used to illustrate and assess the plausibility of these theoretical concepts. Current landscape developments in Saskatchewan, including the emergence of concerns for human-induced climate change, the development of wind power and even the re-emergence of nuclear power generation as a policy option, may facilitate a transition towards greater sustainability. These sustainability paths are juxtaposed against the development of Saskatchewan’s oil sands and the development of carbon capture sequestration technology. Possible future alternative pathways to sustainable power production are outlined and critiqued in the current Saskatchewan governance context.