Approximately 60% of deployed service members leave behind immediate family members, and although military families tend to be adaptive and resilient, evidence suggests that deployments are challenging and difficulties can arise during transitions and family separation, especially for adolescents. Grounded in the family attachment network model and the ABC-X model of family stress, the current study utilized a sample of 204 military families with an active-duty father, civilian mother and adolescent and examined parents' perceptions of adolescents' difficulties during deployment in relation to all three family members' perceptions of the adolescents' mental health (i.e., anxiety symptoms) following deployment. First, analyses of measurement invariance indicated that service members and civilian parents were generally reporting on the same underlying construct of their adolescents' difficulties during parental deployment. Next, a structural equation model demonstrated considerable overlap in service member and civilian parent reports of their adolescents' difficulties during a parental deployment (r = 0.47). Finally, both parents' perceptions of adolescent difficulties during parental deployment were related to their own perceptions of the adolescent's current anxiety but not to the adolescents' reports of their own anxiety symptoms or to the other parent's report of the adolescents' anxiety symptoms. Findings provide support for utilizing these theories in combination, such that disruptions to the family system, and the attachment relationships within that system, in one stage of the deployment cycle, may imply that there are implications for individual-level functioning, namely, anxiety, in the next stage of the deployment cycle. Findings also underscore the importance of examining our measurement tools and collecting data from multiple family members to understand family processes.