Skepticism and naturalism bear important connections with one another. Do they conflict or are they different sides of the same coin? In this paper, by considering the ways in which Sextus and Hume have examined these issues, I offer a Pyrrhonian response to Penelope Maddy's attempt to reject skepticism within the form of naturalism that she calls “second philosophy” (Maddy, 2007, 2017) and to Timothy Williamson's attempt to avoid skepticism from emerging within his knowledge‐first approach (Williamson, 2000). Some lessons about (...) Pyrrhonism result. (shrink)