Interpersonal relationships are the recent focus of research identifying protective factors in adolescent psychological health. Using an attachment theory perspective, this study examines the relationship of normative attachment strength and individual differences in attachment expectancies on self-reports of depression and stress in 511 Australian high school students. Attachment reorganisation was demonstrated, but only father attachment uniquely predicted self-reported stress. Age moderated the relationships between peers and depression and stress among romantically involved adolescents. Individual differences in attachment styles, particularly anxious attachment, were most predictive of adolescent psychological health. These findings highlight the complexity of adolescent attachment relationships and suggest that interventions target both normative and individual factors in adolescent development to enhance adolescent psychological health.