The military’s primary mission is to prevent, fight, and win wars. A critical key to its success is the military’s dual mission of force health protection that translates to preventing and treating the physical and psychological wounds of war in order to preserve the fighting force. To accomplish both missions, the military relies extensively on documenting its lessons learned to build upon its successes and prevent avoidable disasters caused by repeating its failures. The military’s commitment to learning battlefield lessons are directly responsible for unparalleled technological and medical, life-saving advances that greatly benefit both military and private sectors. However, the evolution of modern industrialized warfare’s capacity to kill, maim, and terrorize has exceeded the limits of human endurance whereby psychiatric casualties have outnumbered the total of combatants, both wounded- and killed-in-action, since the Second World War. Psychiatric attrition and skyrocketing costs associated with psychiatric treatment and disability compensation threaten the military’s capacity to accomplish its primary mission as well as risk straining the finances of society, thereby presenting a significant mental health dilemma. Central to the military’s mental health dilemma are two competing alternatives: (1) to fulfill its moral, ethical, and legal obligation of preventing and treating war stress injuries by learning from its documented lessons learned, or (2) develop strategies to avoid learning its war trauma lessons in order to avoid psychiatric attrition, treatment, and pensions. The first option conjures deep-seated fears of mass evacuation syndromes should the military treat mental wounds similar to physical injuries. Consequently, the military has embraced the second option that inevitably has been harmful to veterans, their families, and society, in what we refer to as the darker side of military mental healthcare. In this, the first of a three-part review, we examine the contextual factors framing the military’s dilemma and 10 strategies utilized to avoid learning its war trauma lessons, which will be explored in-depth in parts two and three. While disturbing, these signs of failures are readily ignored and dismissed by a war wary republic. To our knowledge, such an analysis has never been undertaken before or publicly disclosed. When considered as parts of the whole, the findings point to a critical need for improvement in treating military psychological injuries in the war theater.