On Certainty remains one the most provocative and challenging parts of Wittgenstein's intellectual legacy. Philosophers generally read this text as an assault on the traditional sceptic/anti-sceptic debate. But some commentators identify political-specifically 'conservative'-sentiments at work here. Others embrace Wittgenstein's (alleged) 'pluralism', while those less enthused think the latter collapses into relativism. Although this mixed reception is, I will argue, partly due to Wittgenstein's own troubled engagement with the central themes of On Certainty, the real difficulty and value of this text lies in its intertwining questions of epistemology, religious belief and ethical-political judgement.