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The study examines differences in the school-to-work trajectories (STWT) across time and federal states in Germany. It uses administrative data of school-leavers with at most intermediate-level certificates from 2009, 2011 and 2013. While the chances of a smooth STWT improved by increasingly favourable economic development after 2009, the relative disadvantage of school-leavers with low certificates continued. The probability of a problematic STWT remained unaffected and did not vary according to state differences in subsidized training schemes.