This chapter explores some of the challenges of interpreting Indian philosophy by examining three exemplary puzzles: the manner in which philosophical authors employed the idea of the Cārvāka system, a school of thought said to be at once skeptical, hedonistic, and materialist; the meaning of “freedom” in classical India; and the limits of reason as suggested in the work of the notable Vedānta philosopher Śaṅkara. The essay seeks to demonstrate that even in areas such as these, which are assumed to be relatively well known, matters may be not quite so clear as people are wont to believe. The field remains open to, and in need of, revised and improved interpretation of the familiar no less than of topics that seem more obscure.