Costa Rica, after its independence in 1821, developed a school-based vocational-technical education system, but since the 1990s, the country has been trying to move toward a dual apprenticeship system as a strategy to reduce youth unemployment. However, so far, no clear connections have been established between dual apprenticeships and an effective decrease in unemployment. Moreover, the limited involvement of the business and trade union sector has hindered its large-scale adoption. This chapter theoretically analyzes the tensions inherent in the process of implementing dual apprenticeships in Costa Rica and their possible impact on youth unemployment and also uses unemployment data from 2010 to 2024 to analyze their historical behavior. It concludes that although this strategy is presented as a means to promote inclusive educational and labor trajectories that favor youth employability within a framework of legal structures for decent work, no solid scientific and political links have been established between dual apprenticeships and the reduction of youth unemployment.