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This longitudinal study of N = 1,566 adolescents investigated the protective role of optimism in adjustment to parental separation, focusing on two salient challenges faced by adolescents, namely academic achievement and self-esteem. Based on latent change models, the results indicated associations between parental separation and short-term declines in academic achievement as well as short-term and longer term declines in self-esteem. Although optimism in general showed positive associations with academic achievement and self-esteem, its role as a protective factor proved to be particularly important for academic achievement in adjustment following parental separation.