To underscore both the diversity and severity of energy security tradeoffs, this study examines five different energy security policy packagesdfive distinct strategies aimed at reducing oil dependence, enhancing energy affordability, expanding access to modern energy services, responding to climate change, and minimizing the water intensity of energy production. It identifies both compelling synergies and conflicts between each of the five strategies. The central value of the study is that it turns on its head the widely accepted notion of a “portfolio approach” or “all of the above” strategy to energy policymaking. To make this case, the article begins by elucidating the complexity and multidimensionality of energy security as a concept. It then introduces our five energy security policy packages to illustrate how some energy security objectives complement each other whereas others counteract each other. It concludes by noting that energy security is not an absolute state, and that achieving it only “works” by prioritizing some dimensions, or policy goals and packages, more than others.