Annually, a large proportion of young people transition to vocational preparatory programs due to the lack of training positions. This study examines the educational and employment trajectories of around 200 young individuals who attended a vocational preparation year in Berlin, starting from the age of six. In the general education sector, particularly high rates of grade repetition and low academic success can be observed. After the vocational preparation period, it becomes evident that less than half of the young people manage to achieve sustainable integration into vocational training. Furthermore, the results indicate very narrow time windows in which a transition to training can be realized. The findings carry implications for the need to increase flexibility in transition options within the vocational education system.