This chapter examines narrative representations of slavery in early monasticism. It then reads these accounts in light of extant material remains and in conversation with prescriptive regulatory precepts. Such contextualisation necessarily situates emergent communities within a late-Roman world where ‘attitudes of slaveholders [remained] constant’ and the ‘conditions in which slaves lived and worked persisted from generation to generation’ (Glancy). As the cracks and fissures routinely glossed over in more seamless depictions underscore the degree to which monastic ideals and ideologies, institutional and relational norms, remain inextricably intertwined with wider Greco-Roman practice, the chapter posits that emergent monastic mores may be best understood as at once dismantling and reinscribing the structural hierarchies of slavery. Against this landscape, where the jagged edges of lived experience remain patent, the chapter simultaneously premises reconceptualisations that effectively disrupt both static idealisation and wholesale denigration. Through engaging reading strategies that resist the limitations implicit to binaried definitions of practice, its aim is to breathe life into the larger than life.