Members of the Armed Forces, at all levels, are required to make decisions in which every outcome appears to be averse and high risk. Neither the current military decision-making process nor contemporary psychological theory (e.g., recognition-primed decision-making) satisfactorily explains the process of making decisions such as these. This chapter discusses the prevalence of least-worst decisions, showing that they can occur at all levels, from the President’s decision to use a military option (e.g., in Syria) to the soldier on the ground who must decide whether to shoot or not (and the implications of the former on the latter and vice versa). The chapter also shows that effectively navigating combat, at all levels of command, is not a case of being able to select the best choice but, rather, often being able to grapple with choosing the least-worst.