Looking at the early educational activities of the anti-caste movement in the Western Indian Bombay Presidency (1848–1882), the article sheds light on the diverse, and sometimes contradictory social effects of the colonial encounter. The military defeat of the Maratha Empire, the setting up of colonial educational governance, and the emergence of missionary education had disrupted social and religious certainties. In this moment of crisis, reformers turned to education to intervene in the ongoing social transformation processes. From the perspective of the shudra-atishudra – the serving, labouring, and untouchable castes, who formed the lowest stratum of Western Indian society – the new political situation provided a space to challenge the established structures of caste and gender domination. The article starts with a discussion of colonial- governmental and missionary educational interventions, and proceeds to analyse anti-caste radicals’ educational activities against this background. Schools, popular literature, and public performance aimed to create a reflexive knowledge among the shudra-atishudra about their own position in society, and the ways to change it. Finally, the article explores the anti-caste movement’s varying interpretations of the changes in education and society. While anti-caste writers of the 1850s welcomed the new educational opportunities, their voices were highly critical of colonial education policy in the 1880s. In the nineteenth century’s struggles over caste, gender, and education, privileges and exclusions had been reworked in a colonial- modern framework. Still, important steps had been taken towards democratising and universalising Indian education.