Purpose: The Italian school-to-work transition (STWT) is astonishingly slow and long in comparison to the other EU countries. The aim of this paper is to analyze its determinants comparing the Italian case with Austria, Poland and the UK in a gender perspective. Design/methodology/approach: The analysis is based on a Cox survival model with proportional hazard. The smoothed hazard estimates allow us to identify the non-linear path of the hazard function. Findings: We reckon that the actual length of the transition to a stable job is around 30 months. Conversely, it is less than one year in the other countries. Women are particularly penalized, despite being on average more educated than men. Attaining a tertiary degree or a vocational path of education at high secondary school strongly increases the hazard rate. The smoothed hazard estimates support the hypothesis of positive duration dependence at the beginning of the transition and slightly negative thereafter. Practical implications: Stimulating economic growth and investing in education and training are important pre-conditions for shortening the transition. Originality: Despite the duration of the STWT is one of the most important indicators to measure the efficiency of the STWT, it is not easy to measure. The authors build on their previous research work on this topic, but relaxing the assumption of a monotonic hazard rate and using the flexible baseline hazard approach to test for the existence of non-linear duration dependence. Furthermore, they extend the analysis by including student-workers who attended a vocational path of education, in order to detect its effectiveness in allowing young people finding a job sooner.