The aim of this paper is to analyze the conditions and processes governing the entry of low-achieving German adolescents into vocational education programs taking the regional context into account. The theoretical underpinning is rendered by labor market theories, by micro-sociological tenets, by value-expectancy-theories, and by models connecting socio-cultural and psychological influences. Light is shed on the relationships between individual cognitive and motivational dispositions of the adolescents, their society- and mobility-related characteristics as well as regional factors on the one hand and training opportunities on the other. Using a longitudinal design (NT1=2.671) with four measurement points we assessed individual resources (e.g. achievement in math) and attitudes, insofar as they are related to learning and work, to career, and to performance on the job as well as contextual factors (e.g. regional eco-nomic and demographic data). These variables are used as predictors for the realized individual transitions and pathways after leaving general school. The results show a ‘creaming effect‘ at the expense of cognitively challenged adolescents in economically disadvantaged regions. Moreover, it could be shown that the adolescents‘ percep-tions of the regional training opportunities have a distinct impact on their search patterns and their application strategies.