This qualitative study chose the cadet troop of FHK College as its research target because the culture of its training program promotes helping principles and the cadets will potentially be future professionals serving the mental health of the Taiwanese. Using focus groups, this study explored the experiences of the cadets and how military discipline influenced helping work in the military field in terms of military rank culture. Furthermore, this study discusses what has been learned in the practice of Taiwan military mental health primary prevention and social work education. Results indicate that cadets learn to adjust themselves from the conflicts between commanding and helping and develop tacit knowledge. It is important to realize how military rank culture influences military personnel’s interactions. Because of bureaucratic and institutional factors, distinct and varied dynamics occur among cadet troops when helping principles meet military discipline. From the viewpoint of social work, the authors then discuss the practice of Taiwanese military mental health primary prevention and point toward a paradox between helping principles and military bureaucratic culture largely due to the military mental health framework involved inside the chain of command. All of the helpers are directed by their commanders rather than their helping supervisors. Some cadets develop a new vision from group experiences with their troops which is outside of the social work classroom education context. The authors argue that Taiwan military social work should develop contextualized, practical knowledge compatible with its dual focus: (the cultivation of both) concern about both organizations and soldiers. It should also raise awareness of rank influences and take suitable actions when faced with the inherit conflicts within the scheme. Suggestions for policy and practice are given.