Using a life history approach, this article explores the ways in which women in the military who are also mothers learn to embody various masculinities and femininities as they negotiate workplace gender processes. Complex intersections of gendered communities of practice result in the participants' learning to variously understand, accept, shape and/or resist interlinked personal, professional and organizational gendered discourses. First, I discuss theories of learning in communities of masculinity and femininity practice, exploring how they connect to the military context. Second, I explain how life history methodology enables an examination of participant learning through personal, organizational and societal constructs. Third, I detail the findings as they relate to the complex ways in which women in the military learn to embody various masculinities and femininities as they negotiate workplace gender processes. Last, I conclude that participants transgressed and reinforced certain boundaries between various military communities of masculinity and femininity.