This essay reconsiders Wittgenstein’s relation to the pragmatist tradition. I first discuss, from a pragmatist perspective, three key issues of Wittgenstein studies: the distinction – invoked in recent discussions of On Certainty, in particular – between the propositional and the non-propositional (section 2); the tension between anti-Cartesian fallibilism and what has been called the ‘truth in skepticism’ in Wittgenstein (section 3); as well as the relation between metaphysics and the criticism of metaphysics in Wittgenstein’s philosophy, and Wittgensteinian philosophy more generally (section 4). I then proceed to a more metaphilosophical consideration of yet another problematic dichotomy, the one between deconstructive (therapeutic) and (re)constructive or systematic, argumentative philosophy – which, I argue, the pragmatist, together with Wittgenstein, ought to overcome rather than rely on (section 5). After having gone through these open issues in Wittgenstein scholarship at a general level, I briefly apply my considerations to the philosophy of religion, which is an important field of inquiry for both Wittgensteinian and pragmatist thinkers (section 6).