The relationship between sociology and morality is a complex one. There is a vibrant tradition of moral sociology which is not moralistic in a naïve sense. It does not just want to reproduce existing conventions of society blindly as it strives to interrogate morality from the point of justice. This chapter discusses the contours of a critical moral sociology through a dialogue with Jürgen Habermas and Sri Aurobindo, and then strives to explore its limitations. It pleads for a movement from discourse ethics to spiritual transformations. It also explores new pathways of post-conventional moral development.