Well-being is realised through the interaction of the individual's desires and capacities, and external contexts. Contexts in postcolonial societies diverge from the assumptions of functioning liberal democratic states and capitalist economies often assumed in theories of schooling. Instead, these contexts are characterised by poverty and inequality, cultural diversity, and ongoing projects of state and nation-building. Through case studies of two rural communities in India and South Africa, this paper analyses the role of postcolonial contexts in shaping well-being opportunities through schooling in these contexts. It highlights the contested nature of this relationship in cultural, economic, and political spheres.