A substantial step in The Claim of Reason, Stanley Cavell's critique of the modern epistemological tradition is a unique and intricate endeavor, supported by different intuitions and strategies. In light of this, the central aim of this paper is to articulate the main theoretical and methodological basis that govern such reading of traditional epistemology's procedures, and, indeed, the entire Cavellian philosophical project, aiming to provide an indispensable groundwork for those who intend to delve into the American's work. Thus, the following are presented: the foundations and methods of ordinary language philosophy, primarily inherited from Austin, and sophisticated by Cavell in Must We Mean What We Say?; the innovative theses concerning the modern skeptical problem proposed by Thompson Clarke in The Legacy of Skepticism; and the principles of Cavell's unorthodox interpretation of Wittgenstein's Philosophical Investigations, supported by the analysis of grammatical criteria. Placed side by side, these three ideas help clarify the inaugural hypothesis of The Claim of Reason, that the classical notion of knowledge as certainty must be mistaken. Finally, Cavell's alternative suggestion of knowledge as acknowledgement is briefly addressed and situated within the broader landscape of the theories of knowledge. With that, the intent is to show that the Cavellian criticism aims not only to diagnose an epistemological concern born in modernity, but to also argue that it cannot be eliminated with a refutation of skepticism, but only recognized through the acceptance of its truth.