This paper examines the predicament of the Dalit youth in their pursuit of higher education through a qualitative study in a low-income locality of Delhi. In absence of control over material resources historically, education offered promise in liberating socially excluded groups for its instrumental link with modern occupational structure. The policy of universal public education backed up with affirmative action in India has formally aided its access across sections. Even as the participation of the hitherto marginalized groups has been increasing manifold, privatization and marketisation in the education sector under the neo-liberal regime have transformed the educational landscape. Dalit youth is largely segregated into low-quality distance and social sciences education. The paper discusses various constraining and motivating factors embedded within and outside the neighbourhood and educational institutions which shape their educational interests, choices, and decisions. It elaborates on how cumulative socio-cultural, spatial, and historical disadvantages continue to shape the process of educational exclusion, even when these groups live in a metropolitan city amidst educational institutions. However, we also stress that the state policies, informed mentors, shared aspirations, and diversity in socio-cultural interactions hold the potential to alter and widen educational aspirations, access, and outcomes.