Can ancient skepticism be a serious, vibrant, and fruitful interlocutor for contemporary philosophy? The volume addresses this question in a collection of essays that examine ancient skepticism not as a mere doctrine of the past, but as a rich and powerful source that continues to challenge current debates on a wide range of topics—truth, plausibility, belief, action, the way of life, language, meaning, rationality, history, and the nature and aims of philosophy. The volume is grounded in the recognition that ancient skeptical strategies offer valuable insights 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 ruptures across different philosophical periods.