Widely chosen by students of society as an approach under which to labour, emancipatory, liberatory or, otherwise put, critical social thought occupies a position between knowledge and practical action whose coherence is taken for granted on account of the pressing nature of the issues it attempts to deal with. As such it is rarely subjected to scrutiny and the methodological, conceptual and moral challenges it faces are not properly identified. The contribution of this article is to raise these problems into (...) view clearly and unambiguously. This is undertaken via a careful examination of Alice Crary’s recent work, in which she attempts, firstly, to defend a left-Hegelian version of Critical Theory by relating it to the work of Peter Winch and, second, to issue a set of methodologically radical recommendations on employing the sensibility-shaping powers of the literary form. The article aims to deepen our understanding of the fundamental tensions between the Critical Theory and Wittgensteinian traditions, which Crary attempts to bring together and, ultimately, of those crucial features of our moral practices that frustrate the enterprise of critical social thought. (shrink)