In this paper, we investigate the relationship between a graduate’s field of study and probability of finding a stable job in a labor market which is flexible as regards atypical jobs but highly protective regarding stable jobs. We apply a discrete-time hazard model, taking into account unobservable heterogeneity, to analyze the transition to a stable job of students who graduated from the University of Calabria in 2004, at one, three and five years distance. Main findings indicate that, after controlling for a wide range of characteristics, Engineering graduates have a higher probability of finding a stable job than graduates in Economics and Business followed by those with a degree in Sciences, Political Science, and Humanities. These results confirm that, even in a deprived area, investing in occupational specific human capital can be seen as an “insurance” against the risk of unemployment or an unstable job.