This paper provides a reinterpretation of some of the most influential skeptical arguments, Agrippa’s trilemma, meta-regress arguments, and Cartesian external world skepticism. These skeptical arguments are reasonably regarded as unsound arguments about the extent of our knowledge. However, reinterpretations of these arguments tell us something significant about the preconditions and limits of persuasive argumentation. These results contribute to the ongoing debates about the nature and resolvability of deep disagreement. The variety of skeptical arguments shows that we must distinguish different types of deep disagreement. Moreover, the reinterpretation of skeptical arguments elucidates that deep disagreement cannot be resolved via argumentation.