The present study examined the effect of level of traditional masculine gender role norms as well as the moderating effect of cognitive flexibility on community reintegration outcomes in a sample of 60 male military veterans who had sustained a traumatic brain injury during deployment. Data were collected through self-report measures and cognitive tests. Results suggested that greater endorsement of traditional masculine gender role beliefs, attitudes, and behaviors was significantly inversely related to the community integration domains of relationships and living skills and not significantly related to work and leisure. The effect of masculinity on healthy living skills was moderated by cognitive flexibility; the protective effect of low masculinity on living skills was only present if the veteran also had high cognitive flexibility skills. Results are discussed in the context of gender role strain, potential limiting aspects of stereotypy on recovery and reintegration, and the importance of cognitive flexibility in the recovery/reintegration process.