To win on today's complex and competitive battlefield our military leaders have had to try to shed decades of organizational culture that emphasized control and stability as the solution to solving problem sets. Instead, today's leaders must be adaptive and agile in their analysis and development of innovative solutions to the complex challenges of the 21st century. Today's security environment requires men and women in uniform to think critically and be creative in developing new strategies and solutions. These skills will allow our military leaders to maintain the operational initiative against an enemy who is by nature adaptive and always evolving to overcome the tremendous advantage in technological and material overmatch of the United States and many of its allies. This paper argues that the U.S. Army should continue its bold initiatives in its current Campaign of Learning and go even further. It should develop creative leaders who can exercise adaptive leadership with the capacity to provide learning environments within their organizations. Included in the paper is an analysis of adaptive challenges facing the Army. Specifically, the Army espouses the need for decentralized operations and operational adaptability, but the author argues that the Army culture is driven by control, stability, and risk aversion. A case study 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, Iraq. 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 today's reality. The case highlights leaders who are constrained by assumptions and therefore suffer the consequences of failing to adapt quickly to a changed environment. Emphasizing the import