This chapter summarizes key findings from the research project Alternative Routes to Higher Education Eligibility (ARtHEE). Based on data from the German National Educational Panel Study (NEPS), we show that the expansion of alternative routes to higher education eligibility, which has followed from reforms in the 1960s, has been largely ineffective in reducing social inequality in access to higher education. We argue that this is due partly to unintended effects of this expansion of alternative pathways that resulted in diversion processes among students of disadvantaged social origin. These diversion effects channel such students into non-academic secondary school tracks and expose them to learning environments that differ from that of the academic school track. We provide empirical evidence suggesting that exposure to these learning environments affects students’ educational aspirations and cognitive development in a way that eventually lowers their chances of staying on a trajectory leading into higher education.