A fundamental observation of the 21st century is the substantial drop in permanent employment occupations. In this paper, I seek to understand the geographic variation in apprenticeship and the consequent permanent employment rates. I exploit a unique setting in Italy to verify whether regional disparities in general education and production systems play a key role in determining vocational apprenticeship rates and in determining how this labor contract creates job matches that persist over time. I find that when the quality of the regional education system is good, the medium-run gains in terms of permanent employment can be moderate. However, a small number of active firms in a region limits the quantity of job entries as apprentices.