This essay attempts to describe the complex dialectical interplay among the contrasting rational, sceptical and naturalist elements that appear in Hume’s philosophy, ie. His famous work: Treatise of Human Nature. At the same time we shall try to show that, contrary to Hume’s own evaluation of that section, it is the skeptical element, in which the unreliability of reason is supposedly demonstrated as opposed to remain hidden from us, that deserves to explore by us. With these two goals in mind and in order to make it easier for us to follow the inevitable twists and turns of the dialectic, we have introduce Stroud, Strawson and Pappas’s view about Hume’s skepticism, try to give a new explanation from a epistemological point of view.