The present study examined the timing of behavioral autonomy transitions in two same-aged cohorts of East German adolescents assessed in 1991 and 1996. An earlier timing of autonomy privileges was associated with higher deviant behavior. A later timing of autonomy privileges and responsibilities was linked to structural constraints, specifically, to parental unemployment. Between 1991 and 1996 significant timing differences were observed for some autonomy transitions in the East, implying an adaptation to Western timetables. Our findings illustrate the plasticity of autonomy transitions under conditions of social change.