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This research investigates university students' dropout by focusing on the role of students' educational backgrounds and labour market conditions of both origin and destination areas. We exploit the administrative data from the Italian National Student Archive related to students enrolled in an Italian university between 2011 and 2018 by applying a two-step approach to separate students' career disruption effects related to their high school background, attended university, and degree program from those associated with labour market and socioeconomic conditions (e.g., unemployment, income, number of firms). In the first step, the effect of secondary schools, degree programs, and universities on students' performance in terms of earned formative credits is estimated using fixed regression models. In the second step, the estimated fixed effects are used in a multinomial logit model to account for the role played by high schools and universities in assessing the effect on students' career disruption of the labour market conditions of both origin and destination areas.