In 610 CE, Babai the Great journeyed across Persia to ensure that monasteries were orthodox in their instruction of monks. Babai’s journey is just one that shows the understudied Syriac Church of the East was a flourishing landscape where the line between a school and a monastery was not always clear. This dissertation uses saints’ lives, local histories, and monastic rules to study the ways Christian monks and students lived day-to-day in Late Antique Mesopotamia.