This article analyses to what extent gender affects the quality of the school-to-work transition in Spain, paying special attention to workers’ educational attainment. We estimate a four-equation system that explains the main obstacles young people face in their insertion process: part-time work, overeducation, fixed-term contracts and long unemployment spells; the model also considers the impact of the latter variable on the other three. Moreover, a synthetic indicator of transition quality based on the estimation of this model is developed. We conclude that men experience a better insertion process than women at every level of education (except for higher vocational training), although the gender gap is greater for long-cycle university programmes. Furthermore, when field of study is considered, men from most specializations enjoy a smoother transition than their female counterparts; nevertheless, women have the advantage in some female-dominated fields. A further analysis of gender differences reveals that they are due to the fact of being male or female to a great extent. The results also highlight that school-leavers from work-oriented programmes and those specialized in fields that provide them with more specific skills are more likely to succeed in the transition.