This dissertation is an historical inquiry into the origins of scholasticism within the Nyingma (rnying ma), or "Ancient," sect of Tibetan Buddhism, in the form of the establishment of the monastic college or shedra (bshad grwa) called Dzogchen Sri Singha (rdzogs chen srisengha) by the Nyingma monk Gyelsay Shenpen Taye (rgyal sras gzhan phan mtha' yas, 1800-1855). Given the fact that the Nyingma sect's institutional origins predate the establishment of Dzogchen ?r? Singha by centuries, and given the additional fact that scholastic institutions began to flourish in Tibet during the twelfth century, the fundamental question this dissertation seeks to answer is why it took until the nineteenth century for the Nyingma sect to develop scholastic institutions of its own. On the basis of a general analysis of Tibetan Buddhist scholasticism, and an examination of the nature of Nyingma sectarian identity in historical perspective, the dissertation provides an account of the intellectual and institutional forces that first militated against, and then enabled and encouraged, the nineteenth century development of properly scholastic institutions within the Nyingma sect. In particular, the work emphasizes the philosophical importance of "gradualism" -- the view that the understanding and practice of esoteric Buddhism necessarily depends upon the prior understanding and practice of exoteric Buddhism -- and the institutional importance of large-scale monasteries for the eventual development of Nyingma scholasticism.