Adolescence is considered to be a transitory phase in the life course. It is hypothesized that failure in school, which carries the risk of an occupational and social “downward mobility” in the future life course in comparison to the family of origin, can function as a social “stressor” which has detrimental effects on the social and emotional climate within the family and manifests itself in symptoms of stress such as psychosomatic disorders. The results are based on a questionnaire survey carried out with a representative sample of 1717 students aged 13–16 in West Germany. The data support the hypotheses: psychosomatic symptom frequency is reinforced when adolescents experience failure in school and social and emotional conflict in their relationships with parents. Multivariate analysis shows that these effects are interconnected: failure in school has a direct effect on the frequency of psychosomatic disorders, and an indirect effect by influencing social and emotional conflicts in the family. The underlying causes for the tensions between adolescents and their parents are conceived in the social and economic opportunity structures of the society.