This paper presents the results of 3 studies examining the relationships of parental attachment, peer attachment, and self-esteem to adolescent psychological health. A model is presented in which parental attachment directly influences both psychological health and self-esteem and the influence of peer attachment on psychological health is totally mediated by self-esteem. Using structural equation modeling, Study 1 evaluates the model on a sample of 1998 Norwegian high school students (aged 12-19 years). With some modifications it is found to be a satisfactory fit. Study 2 replicates Study 1 using a sample of 358 Australian high school students (aged 15-18 years). A multisample analysis revealed no significant differences between the model for Studies 1 and 2. Study 3 was a further successful replication employing alternative measures of the constructs considered with a sample of 345 Australian high school students (aged 15-19 years). The major finding from all 3 studies is that the role of peer and parental attachment on psychological health is primarily meditated by self-esteem. Implications for research elucidating the links between attachment and specific aspects of self-esteem are discussed.KEY WORDS: attachment; depression; self-esteem; adolesence.