This monograph leads with a case study which provides a means for analyzing the complexity of organizational leadership in the contemporary security environment. The study presents a high stakes problem-set requiring an operational adaptation by a cavalry squadron in Baghdad. This problematic reality triggers the struggle in finding a creative solution, as cultural norms serve as barriers against overturning accepted solutions that have proven successful in the past, even if they do not fit in the context of the reality of the present. The case study highlights leaders who are constrained by assumptions and as a result, the consequences of failing to adapt quickly to a changed environment. Through reflection and a willingness to experiment and assume risk, the case study transitions into an example of a successful application of adaptive leadership and adaptive work performed by the organization.