There are some tantalizing suggestions that Pyrrhonian skepticism has its roots in ancient India. Of them, the most important is Diogenes Laertius’s report that Pyrrho accompanied Alexander to India, where he was deeply impressed by the character of the “naked sophists” he encountered (DL IX 61). Influenced by these gymnosophists, Pyrrho is said to have adopted the practices of suspending judgment on matters of belief and cultivating an indifferent composure amid the vicissitudes of ordinary life. Such conduct, and the attitudes (...) that it embodied, became inspirations to later skeptical thinkers. It is a fact that practices of the sort attributed to Pyrrho are richly evident in a number of ancient Indian philosophical and ascetic movements. On this basis, attempts have been made to determine the identity of these gymnosophists and, further, to pinpoint the dialectical tropes within Pyrrhonism that may have their basis in Indian thought. But despite these attempts, and in the absence of any new discoveries, these suggestions will likely remain just that. The paucity of the historical data and the problematic nature of the data itself prevent us from reconstructing a solid bridge between ancient India and Greek skepticism that may serve as the basis of robust historical theorizing. Classical India does, however, lay claim to a sophisticated and diverse culture of epistemological reflection, which includes a number of innovative skeptical thinkers deserving study on their own merits. This chapter is meant to provide such a study, or perhaps more accurately, a prolegomena for such. After some initial ground-laying, I will discuss three leading Indian skeptics and situate them historically and conceptually within the network of competing schools that comprise classical Indian philosophy. They are Nāgārjuna (c. 150 CE), the founder of Madhyamaka Buddhism, Jayarāśi (c. 800), associated with the Indian materialist tradition, and Śrīharṣa (c. 1150), a thinker connected to the school of Nondual (Advaita) Vedānta. (shrink)