Transitions to upper secondary education are of crucial importance to understanding educational inequalities. They are also vital to explaining the contemporary dynamics of Early School Leaving (ESL). Global hegemonic discourses around educational transitions and ESL 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 (VET) and to guidance in order to smooth educational transitions, reduce ESL and meet the needs of the knowledge-based economy. The aim of the article is to problematise the linear relationship between ESL, VET and guidance policies representing the dominant contemporary rhetoric concerned with ensuring smooth transitions and opening long-term educational pathways for young people. The paper provides an indepth 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 useful analytical resource to inform critical policy analyses of educational transitions and their implications in terms of social inequalities.