This paper explores the ramifications of masculinized military culture and operational stress on cross-cultural adaptation. The author examines how characteristics of military culture may obstruct effective cross-cultural adaptation by promoting a hypermasculinity that tends to oppose effective management of trauma, and thereby suppresses skills of social interaction (e.g., adaptive emotional resilience, behavioral flexibility) that could assist military members with cross-cultural interactions. Because these cultural aspects may tend to exacerbate difficulties members have when transitioning between cultures and dealing with trauma effects, possible approaches in counseling intervention to mitigate these effects are discussed.