The growing educational aspirations in India reveal and affirm the optimism associated with the institution, especially its promise of upward social mobility for excluded groups mired in intergenerational poverty, caste-based occupations and a cycle of stigma and humiliation. This aspiration and faith are visible among historically marginalized sections where parents with limited means are eager to make personal sacrifices to send their children to fee-paying, English-medium private schools. These aspirations, however, must be studied vis a vis three factors: stratified and segregated education system in contemporary, neoliberalizing India, entrenched nature of historical disadvantages, post-schooling opportunities and persistence of discrimination in different, often subtle forms. In this context, it becomes pertinent to revisit Dr. B.R Ambedkar’s (1891–1956) philosophy of education and how he positioned education as central to his project of emancipation of Dalits and other oppressed groups. This article thus tries to engage with his perspectives on the emancipatory and revolutionary potential of education for historically disadvantaged communities and focuses on his ability to accurately capture not just the promise but also the limitations of education as he saw and experienced it. It highlights his astute sociological observations about practices of stigma and exclusion within and beyond the classrooms and an unequal institutional context which promises success but sets one up to fail. His insights and roadmap on how these structures can be dismantled have crucial relevance for examining and transforming a highly stratified educational landscape in contemporary India into a more equitable one.