Germany is one of a handful of Western European nations (including Austria and the Netherlands) that maintains a highly-differentiated educational system in which secondary level students are sorted into different schools on the basis on their perceived scholastic abilities. Despite the numerous political and cultural shifts in Germany over the past two centuries, the tripartite configuration of the German educational system has been remained essentially intact since the craft guilds of the early nineteenth century (Baldi, 2010; Ertl & Phillips, 2000; Solga et al., 2014). In fact, "the German educational system is perhaps the clearest and most-studied case of a highly differentiated system" due to its longevity and its influence (Buchmann & Park, 2009, p. 247). This monograph, second in a series of publications by the Pullias Center for Higher Education on career-oriented education in the twenty-first century, investigates other possible regional and national obstacles to the effective implementation of career-oriented education in the United States by turning attention to Germany. In recent years, Germany's vocational education system has been frequently cited as a model for other countries (Euler, 2013; Hawley, 2007; Solga, Protsch, Ebner, & Brzingsky-Fay, 2014). Accordingly, an analysis of the factors that constitute Germany's vocational education system may offer insights into which elements may be feasible and sustainable in the American context.