Based on the German collective skill formation system of dual apprenticeship has received international attention as a potential approach to sustain and develop upper secondary vocational education and training (VET) as an alternative to higher education. Austria, Germany, and Switzerland are considered paradigmatic cases for such a strategy, pointing to similar structures in these countries. At closer look, these three systems also show substantial differences in sustaining upper secondary VET and coping with the repeated crises in the youth labor market. This chapter analyses key differences between these paradigmatic cases beyond structural similarities. International comparative data, literature review, and policy analysis are used as methodology. Results from the analysis of comparative indicators show first that overall education structures do not differ much from European and international averages, second that the expectation of a direct reduction of youth unemployment by apprenticeship is not corroborated by data, third that the employment relation in apprenticeship does not generally induce more emphasis on labor market policy to fight youth unemployment, finally that two of the three systems under focus show different forms of drift of apprenticeship towards tertiary education. The specific elements of apprenticeship generating sustainability and influencing youth unemployment deserve further research.