We critically examine pragmatism's approach to skepticism and try to elucidate its certain limits. The central questions to be addressed are: whether “skepticism” interpreted through the lens of problem-solving does justice to the human condition; and whether the problem-solving approach to skepticism can do justice to pragmatism's self-proclaimed anti-foundationalism. We then examine Stanley Cavell's criticism of Dewey's “problem-solving” approach. We propose a shift from the problem-solving approach's eagerness for solutions to a more Wittgensteinian and Emersonian project of dissolution.