Transitions to upper secondary education are of crucial importance to understanding educational inequalities. They are also vital in explaining the contemporary dynamics of Early School Leaving. Global hegemonic discourses around educational transitions and Early School Leaving shape student pathways in terms of rational and linear choices, assuming equal opportunities for lifelong learning. Simultaneously, the European Strategy attributes key roles to Vocational Education and Training and to guidance in order to smooth educational transitions, reduce Early School Leaving and meet the needs of the knowledge-based economy. The aim of the article is to problematise the linear relationship between Early School Leaving, Vocational Education and Training, and guidance policies representing the dominant contemporary rhetoric concerned with ensuring smooth transitions and opening up long-term educational pathways for young people. The article provides an in-depth analysis of the political construction of the transition from lower to upper secondary education in Catalonia, identifying how it is conceptualised at a discursive level by policy actors and also how it is implemented at the institutional level. The results aim to be regarded as a useful analytical resource to inform critical policy analyses of educational transitions and their implications in terms of social inequalities.