In this chapter, a framework is established using four models of the school-to-work transition: (i) direct transition; (ii) deregulated transition; (iii) regulated overlapping transition; and (iv) shifted transition. The Dual Vocational Training System in Germany is presented as a key to smooth transition from school to work, and it is concluded that the satisfactory transition from the educational to the employment systems for as many young people as possible depends on the training commitment of enterprises to provide attractive traineeships and occupational careers within the framework of dual vocational training.