The present study examined the relationship between adolescents' attachment to parents and their feelings of alienation in the school context by considering the mediating role of adjustment and self-esteem. It was proposed that the degree of attachment to one's parents was associated with adjustment and self-esteem, which in turn predicted possible school alienation. A total of 227 students completed self-report measures on parental attachment, adjustment, self-esteem, and alienation from school. Results were consistent with the attachment theory and related literature that posits that (a) secure attachment to parents was associated with adjustment and self-esteem, (b) secure attachment to parents was negatively associated with feelings of school alienation, and (c) adjustment and self-esteem were a crucial mediators between attachment to parents and school alienation. In addition to enhanced adjustment, the self-esteem of adolescents may be an additional factor in reducing alienation at school. The results also supported the mediator role of self-esteem in the relationship between attachment to parents and adjustment. Finally, the relationship between self-esteem and school alienation were shown to be fully mediated by adjustment. The results were discussed in the context of responsibilities of teachers and school counselors, which may provide both students and parents with the skills to improve social functioning in the school context.