F.W.J. Schelling's precise ways of thinking about skepticism and about its relation to philosophy went through several rather dramatic shifts over the course of his career. This chapter sketches three different positions that Schelling adopted on this subject at different periods. The first of these is a Fichte-inspired position, during the period 1794-1800; the second a Hegel-inspired position, which he held briefly in 1802-3; and the third a Romanticism-inspired position, which he adopted around 1821. Schlegel's initial development of the ideas in question occurred mainly in the Lectures on Transcendental Philosophy that he delivered in Jena in 1800-1, and which Hegel attended. It is an interesting question to what extent Schelling's final philosophical position, the so-called Positive Philosophy that he developed during the last two decades of his life, is continuous with the quasi-Romantic position just described.