In this dissertation I examine the arrival and growth of Jainism in Tamil Nadu, South India between c. 4th century BCE and 7th century CE, and explore the interactions and relationships of Jain monastics, laity, and literati with an emerging political elite. It is both an historical as well as a methodological project, which brings together scholarship from different disciplines to develop a more integrated critical methodology for analyzing archaeological, epigraphic, and literary sources in dialogue with each other. The research builds incrementally, beginning with Tamil-Brahmi lithic inscriptions on caves and rock-cut beds that record donations to Jain monastics, to the appearance of Jains as authors of and subjects within classical Tamil literature and their use of didactic and ethical texts to forge and strengthen relationships with a growing laity and political elite, to the contextualization of this evidence within the broader archaeological landscape of Early Historic Tamil Nadu. The focus then shifts back to the Jain caves/monasteries with an archaeological survey and in situ contextual analysis of the inscriptions and other archaeological features at these hill sites. This project contributes new statistical and geospatial analysis of published archaeological and epigraphical data and has generated new data (including the discovery of new beds and inscriptions) from archaeological survey and mapping of the Jain cave sites in Madurai District, Tamil Nadu. Overall, the dissertation interrogates Tamil literary texts and textual and material artifacts as historical archives and demonstrates the productive potential of a multi-perspectival approach to studying India’s ancient past.