IntroductionGender Advisors (GENADs) have played a key role in the efforts of military organizations worldwide to integrate gender perspectives, and culture change, within the defence and security context. Military organizations, however, continue to face challenges in regard to diversity and inclusion, including limited representation of women and other diverse groups who do not fit the white male, masculine stereotype, and subtle and overt expressions of prejudice and stigma towards under-represented and marginalized groups. In such an organizational context, the integration of gender perspectives has faced challenges, and transformative culture change has remained elusive. In particular, the experience of GENADs suggests that there may be unique challenges to serving as “gender experts” within military organizations. This paper, therefore, examines the lived experience of GENADs within the context of military organizations, as illustrated by GENADs in the Canadian Armed Forces.MethodsWe consider two qualitative studies on the lived experience of GENADs and focus on the shared theme of legitimacy of gender expertise at both individual and systemic levels.ResultsThis analysis highlights challenges that gendered power relations may pose for GENADs as individual change agents, and for systemic, transformative culture change, within existing military organizations, while reaffirming the importance of understanding the lived experience of GENADs in their pursuit of more equitable institutional and operational outcomes.ConclusionUsing social-psychological theories of tokenism, we consider more broadly what it means to be the gender person within masculinized military organizations and conclude with reflections on the potential contours of transformative culture change within the military context.