This study investigates the requirements for sound decision making at the operational level in conditions of high risk. The study first reviews some of the literature related to high-risk decision making. It then investigates two operational level decisions, General Mark Clark’s decision to attack toward Rome in 1944 and General Douglas MacArthur’s Inchon Landing decision in September, 1950. The study identifies a process for decision making in conditions of high risk. The process includes considerations of the operational aim, considerations of key information requirements, assessments relating to the probability and impact of success and failure, and considerations of related actions designed to bolster the success of the high-risk decision. The study illustrates the proposed process by the review of the Rome and Inchon decisions. The study concludes that while decision making in high-risk conditions is largely intuitive in nature, a sound decision-making process combined with the competence of the commander, will aid the operational level commander in making effective high-risk decisions.