This study examined the factors that influenced school adaptation by adolescents from non-military families and military families; subsequently, our research targeted 387 middle school children located in Chungnam province. Questionnaires were used and data analysis was conducted by t-tests and multiple regression analysis. The results were as follows: First, adolescents from non-military families perceived higher levels of attachment to fathers and self-esteem than adolescents from military families. However, the stress level for adolescents from military families was higher than adolescents from non-military families and adolescents from non-military families adapted better to school than adolescents from military families. Secondly, family dynamic, attachment to fathers, and stress influenced school adaptation by adolescents of non-military families and family dynamic and the attachment to friends influenced the adaptation to school by adolescents from military families.