The Army faces a challenge today similar to the one faced following the Vietnam War. The past decade of war created a generation of agile and adaptive leaders focused on the current fight. Army leadership of the 1970s developed concepts that generated the most tactically and technically proficient army in the world exhibited in the tactical success of Desert Storm. The Army leadership of today must prepare the force for the future while engaged in the challenges of today. General Milley’s initiative to make Readiness priority #1 and the recently published Army Directive 2016-05 set the conditions to create an Army prepared to train to win in a complex world. This strategic research project examines the training revolution following Vietnam, the effects of ARFORGEN on how the Army trains, and the initiatives outlined in Army Directive 2016-05. It goes on to examine the change effort of GEN Dempsey to engrain Mission Command in Army culture and compares that effort to GEN Milley’s effort to make readiness priority #1. Highlighting the critical challenge: failing to educate and train those required to execute the requirements and enable them to monitor and correctly report readiness status per the EXORDs puts the entire effort at risk.