Naturalism, construed as the idea that philosophy should be continuous with science, is a highly influential view. Its consequences for epistemology, however, are rather odd. Many believe that naturalized epistemology allows eschewing traditional skeptical challenges. This is often seen as an advantage; but it also calls into question its claim of belonging to the philosophical inquiry into knowledge. This paper argues that skeptical challenges can be stated to defy epistemic optimism within naturalized epistemology, and that there are distinctively naturalistic forms (...) of skepticism. To that end, it outlines some assumptions underlying many attempts to naturalize epistemology. It contrasts these approaches to traditional epistemology and identifies the reasons offered by naturalistic epistemologists to dismiss traditional skeptical challenges. Next, it argues that the problem of skepticism can be sensibly stated within a naturalistic setting. Finally, it contends that there are distinctively naturalistic strategies to argue for skepticism and diagnoses the prospects of naturalism vis-à-vis these kinds of skeptical challenges. (shrink)