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Do short-term contracts facilitate the transition into permanent contracts? We use a rich administrative database for the Emilia-Romagna northern region in Italy from 2008 to 2012 to run a stepping-stone analysis and evaluate which contractual agreement is more likely to lead to a permanent working position. We find that individual specific characteristics make it more likely for a worker to be employed with a specific contractual agreement and that the contribution towards more working stability varies with the previous contract. We conclude that fixed-term positions act more as stumbling blocks than building blocks for open-ended contracts.