This paper considers the social and political pressures that contribute to youth unemployment and school dropout rates in Spain. The multi-faceted problem involves six key issues: first, directing disengaged youth into practical training effectively 'pushes' many students out of the education system. Second, VET's lack of socio-economic attractiveness given the decreasing opportunity costs and status associated with this pathway. Third, employers apparent non-preparedness to give young people without ‘sufficient’ training jobs, or place them in jobs with poor conditions. Further, inequalities emerge from a system that relies on family and social capital to provide job opportunities and financial support. In addition, the ‘transition system’ in place depends on the local context and the specific composition of partners involved (e.g. local training providers, local authorities, social work schemes, schools and companies). Finally, missed opportunities for developing learning spaces that are out of school and activities that research shows can hold more significance than school or job-based training routines, and may be more connected with the further job opportunities. In conclusion, two directions are proposed: the reform of the transition system and improving the guidance and tools used to enable young people to make their journey from school to work.