Observing the many and varied reactions to the Kyoto Protocol, it becomes clear that different governments find themselves in different contexts that eventually direct them toward taking dissimilar positions on energy issues. This paper, through five integrated studies, investigates whether contextualizing energy issues is (are) relevant to support energy policy formulation and evaluation and provides insights into how to operationalize the contextualization. Instead of considering the most widely accepted tools currently used to assess and evaluate energy policy, this research proposes the utilization of a holistic framework that incorporates social, economic and environmental factors as well as their relations to the energy sector to better contextualize global, regional and national energy issues. This framework, which accounts for feedback loops, delays and non-linearity, is applied to case studies to investigate the longer-term performance of selected energy policies. Results of the study indicate the likely emergence of various unexpected side effects and elements of policy resistance over the medium and longer term due to the interrelations existing between energy and society, economy and environment. Furthermore, while side effects and unintended consequences may arise both within the energy sector and in the other sectors, they simultaneously influence society, economy and environment.