This volume poses the following question: can ancient skepticism be a serious, vibrant and fruitful interlocutor for contemporary philosophy? The essays collected here examine ancient skepticism not as a mere doctrine of the past, but as a rich and powerful source capable of continuing to pose challenges to current debates on numerous topics, including, among others, truth, plausibility, belief, action, the way of life, language, meaning, rationality, history, and the conception of the nature and aims of philosophy and the philosophical method. Its justification rests on the recognition that ancient strategies offer insightful views into the problems of contemporary epistemology, while contemporary tools sharpen our understanding of the classical texts. The contributions foster a dynamic dialogue that reveals both continuities and breaks across different philosophical eras.