My interest is the kind of philosophical vertigo that is a theme of Cavell’s work on scepticism. This describes the anxiety that is elicited via philosophical engagement with certain kinds of sceptical questions. There is a standing puzzle about this notion of vertigo, however, forcefully pressed, for example, by McDowell. Why should a resolution of the sceptical problem, one that putatively completely undercuts the motivation for scepticism in that domain, nonetheless generate vertigo in this sense? I aim to resolve the (...) puzzle, in a way that I believe underwrites this Cavellian notion, via consideration of Wittgenstein’s remarks on the structure of rational evaluation in his final notebooks, published as On Certainty. (shrink)