In re-examining the Christianization of the Roman Empire and subsequent transformation of Graeco-Roman classical culture, this volume challenges conventional ways of understanding both the history of Christian monasticism and the history of education. The chapters interrogate assumptions that have framed monastic practice as pedagogically unprecedented, with few obvious precursors and/or parallels. A number explore how both teaching and practice merge classical pedagogical structures with Christian sources and traditions. Others re-situate monasticism within a longer trajectory of educational and institutional frameworks, elucidating models that remain central to the preservation of both Greek and Latin literary culture, and the skills of reading and writing. Through re-examination of archaeological evidence and critical re-reading of signature monastic texts, each documents the degree to which monastic structures emerged in close alignment with urban, literate society, and retain established affinity with classical rhetorical and philosophical school traditions.