Training is the primary effort of The U.S. Army in its day to day operations. It determines the level of readiness for our nation's military. Our training is so complex it requires a system of management to match: this is referred to in Army doctrine as Training Management. Training management is a function all Army leaders perform whenever they plan, prepare, execute, and assess training. It occurs at every echelon within the Army, from teams to corps and beyond. It requires efforts in scheduling, resourcing, coordinating, and equipping to conduct training events. However, no echelon conducts training management independently. The decisions made by a brigade commander regarding training management will impact a company commander's efforts in training management. Training management can aptly be described as a complex system of complex systems. The Army Training Management System is arguably one of the most complicated systems of the U.S. military. The approach of this thesis is to aid in defining just some of the problems and challenges associated with the training management systems, to identify causes and factors that influence these issues, and to suggest potential improvements and ways to overcome these issues. This is an issue that is regularly and routinely analyzed by many military staffs and contacted civilian organizations, and by no means will this thesis provide "THE" answer-but hopefully "establish a foothold" for further analysis that leads to tangible improvements into the system.