Those responsible for ensuring military members are prepared to meet rigorous leadership challenges must do so to the highest professional standard. To that end, this present inquiry investigates possible gender bias within military leadership training, associated curricula, methods of instruction, and cultural infrastructures. Despite several well-intended recruitment campaigns, the Canadian military has long struggled to attract and retain women into its ranks. Women who join the armed services have lower advancement and higher release percentages than their male colleagues. This disproportionate representation is echoed in the markedly fewer number of women holding senior leadership positions, particularly in the operational environments of officer ranks. While this issue might be, in part, the result of a male-dominated military culture, there is evidence that military leadership training inhibits the rank succession of women. Understanding the Canadian Armed Forces (CAF) as a unique organizational culture, we employ institutional ethnography to investigate female underrepresentation in middle and senior leadership positions in the CAF. Specifically, we explore: (a) how leadership training is designed in the CAF, (b) if gender bias in leadership training is connected to a lack of women in middle and senior leadership positions in the military, and (c) what research has been done to identify, reduce, or eliminate gender bias in military leadership training.