There has been a growing body of literature on adolescents in military families since 2002. This research has focused on how frequent moves and parental deployments are two unique potential stressors for youth in military families, and are associated with negative school outcomes. Analyzing data collected from a school in a military community, and data from a national sample of Canadian youth, we examine the impact of military stressors on the school engagement of youth in military families. While we found evidence of residential mobility contributing to negative school engagement outcomes, we also found a positive association between school engagement and parental deployments. Surprisingly, relative to both the civilian youth in our sample and the national sample, military youth exhibited higher levels of school engagement when a parent has been deployed.