This study explores school-to-work transitions in Germany, aiming to achieve a richer understanding of the complexity of labour market entry trajectories while focusing on transition measures. The term transition measures refers to additional training courses that complement the regular vocational education and training system of firm-based or school-based qualification routes. The contribution of supplementary training measures to the school-to-work transitions of young adults is a controversial issue. While programmes aim to ease the transitions of low-skilled youth in the training and labour market, critics point to the risks of long-term subsidised careers or fragmented employment trajectories in subsequent years. By applying sequence analysis to administrative data of the Federal Employment Agency, individual trajectories of a cohort of school leavers with an at-most intermediate school-leaving certificate are analysed for the period 2008 to 2014. The results show a complex picture of ten distinct school-to-work transition patterns. Youth passing through transition measures tend to experience a less continuous but still purposeful transition pathway. We also identify a small number of youth experiencing at-risk trajectories characterised by a highly discontinuous transition process, which points to sustained detachment from the training and labour markets.