Social class, gender, and migration status notably influence social inequalities in the German educational system. Empirical studies reveal that especially male students from Turkish immigrant families belong to the most disadvantaged group with regard to educational opportunities. In order to identify causes for this we reconstruct and contrast biographies of successful and less successful educational careers of male adolescents from Turkish immigrant families. Our theoretical framework is based on the assumption that educational careers depend decisively on the way youths master thetwofold challenge connected with adolescence and migration. Adolescent detachment processes are conceived as intergenerational occurrences (cf. King 2002), in which the quality of intergenerational family relationships as well as the biographical treatment of a particular migration project on the part of the parents play a significant role.