Although the text of the Zhuangzi includes what appear to be skeptical arguments, there has been much debate as to the nature of its skeptical stance, and even whether or not it is substantively skeptical at all. An attempt is made here to engage with both the skeptical aspects of the text and its positive agenda, accepting that the Zhuangzi takes a substantive skeptical stance while also arguing that in doing so it provides a positive account of how to improve our epistemic position. The argument focuses on Zhuangist attitudes to different types of knowledge, specifically what the text refers to as “lesser knowledge” (xiao zhi 小知) and “greater knowledge” (da zhi 大知), and the relationship between the two. An attempt is made to show that the Zhuangist stance is that of a “positive skeptic” who offers wide-ranging practical advice on how to improve our own epistemic situation, while at the same time warning us of the ultimate limits of what we can come to know.