The epistemological problem of the external world asks: (1) “How is knowledge of the external world possible given certain obstacles which make it look impossible?” This is a “how-possible?” question: it asks how something is possible given certain obstacles which make it look impossible (cf. Cassam 2007; Nozick 1981; Stroud 1984). Now consider the following question, which asks: (2) “How is a philosophically satisfying answer to (1) possible?” Skepticism is the thesis that knowledge of the external world is impossible. It (...) therefore represents a negative answer to the first question. Meta-epistemological skepticism is the thesis that a satisfying philosophical explanation of how our knowledge of the external world is possible is itself impossible. It therefore represents a negative answer to the second question. In this thesis, I explore the prospects of meta-epistemological skepticism. In particular, I structure the thesis around two master arguments from for meta-epistemological skepticism. The first argument is that skepticism represents a kind of paradox which requires dispensing with a plausible principle or belief, or even 'platitude', which means that there's no philosophically satisfying response to the paradox (see, e.g., Stroud 1984), and the second argument is “Stroud’s dilemma” (cf. Cassam 2009), that either we explain how external world knowledge is possible by reference to what external world knowledge we have, thereby failing to answer the philosophical question adequately, or else we don't, but then we succumb to first-order skepticism. I argue that the first argument fails to provide adequate support for meta-epistemological skepticism. However, the second argument, Stroud’s dilemma, is plausible and withstands serious objections (e.g., from Sosa 1994, Williams 1996, and Cassam 2009). In short, while the worry emerging out of the 'skeptical paradox' view fails to adequately support meta-epistemological skepticism, Stroud’s dilemma succeeds. Fortunately, it doesn't show that we lack external world knowledge; we rather just can't explain, philosophically, how it's possible. We may have first-order knowledge without understanding how it's possible. This thesis therefore represents a partial defense of meta-epistemological skepticism. Meta-epistemological skepticism is a live option in epistemology. (shrink)