The overriding concerns of Amartya Sen’s writings are about how to promote public action towards achieving an equitable and just society, which particularly addresses the needs of the underprivileged. While his ideas are of great relevance for all developing countries, this is more so for India and Bangladesh—the two countries that provide the socio-economic settings for much of his empirical works. Sen has praised the remarkable progress in many social development indicators that Bangladesh has achieved compared to India, despite having a much lower per capita income and suffering from the same, or even much worse, institutional and policy failures. In fact, the contradictions of Bangladesh lie in its impressive socio-economic progress achieved under extremely poor institutions of economic and political governance. By drawing upon Sen’s writings on issues ranging from human development and social inequalities to the concepts of freedom and “public reasoning”, this essay aims at understanding the factors underlying Bangladesh’s achievements and the challenges that lie ahead.