In this thesis I examine the opportunities for individual agency and social and spiritual autonomy in the seventh-and-eighth-century Anglo-Saxon kingdoms occasioned by the introduction and development of Christian monasticism. The term “autonomy” concerns the degree to which individuals managed to determine the social order and nature, as well as spiritual character, of their ensuing lives through an adherence to monastic practice. Early Anglo-Saxon Christianity assumed a monastic character, and from the outset coenobitic communities acquired and maintained certain rights regarding their internal governance and social development from their ecclesiastic and secular superiors, which conceptually separated religious households from those of the secular nobility. I argue that monastic foundation and participation functioned as an alternative means for social engagement, and spiritually justified and legitimized otherwise culturally unorthodox behaviors such as anchoritic retreat. I consider monasticism’s social and spiritual consequences on individual self-determination. I argue that monastic participation constituted a considerable degree of both collective communal and personal autonomy in regards to an institution’s physical foundation, inner governance through the establishment of a monastic rule, and ability to select subsequent abbots and rulers independent of external influence. I consider the active lives of monastics such as Wilfrid of Ripon, Hild of Whitby, and Ceolfrith of Wearmouth and Jarrow to further suggest the considerable degree of autonomy monastic leaders exercised in their administration of vast monastic properties. I additionally argue that despite the temporal wealth and authority that often accompanied monastic administration, monasticism’s introduction of contemplative eremitism constituted a legitimate alternative to the social obligations inherent in coenobitic practice, and represented an extreme expression of individual autonomy. I finally consider the hagiographic narratives and contemporary social image of anchoritic saints such as St. Cuthbert of Lindisfarne and St. Guthlac of Crowland. I argue that regardless of any power and authority achievable within the physical and temporal world, contemporary religious writers understood complete contemplative withdrawal from society as the ultimate expression of spiritual autonomy, whereby an anchorite positioned their mind towards God alone, and therefore freed themselves from the trivialities and distractions of the world.