This dissertation examines the preaching activities and sermons of Benedictine monks in England in the roughly two centuries before the Reformation. Though the medieval pulpit is commonly envisioned by historians primarily as the domain of the friars, in fourteenth- and fifteenth-century England the black monks regularly made it their own, preaching salvation, chastising negligent priests, and denouncing heresy. In this study I set out to examine Benedictine preaching, especially through their sermons to or about the laity, and what it reveals about their place in the religious landscape of late medieval England. Preaching took on a new importance for the Benedictines in the fourteenth and fifteenth centuries. Competing with other religious orders and foundations for influence and devotion among the laity, popular preaching became a way for the monks to maintain their presence and pastoral leadership in the English Church. Though seemingly incongruous with their vocation, Benedictine writers and preachers defended their popular preaching as an integral part of their way of life, supported by historical precedent and their own interpretation of the Rule. University learning was pressed into the service of training Benedictine brothers as preachers and monastic superiors encouraged monasteries to offer sermons for the laity. As a result the Benedictine black habit became a familiar sight on England's pulpits, right up to the Dissolution when no one wore habits anymore. Through their preaching, the black monks offered an important pastoral service to the Church and secured their place among the friars and others as elite preachers of the day. But their preaching also illustrates the relevance and influence of the Benedictines in English religious life in the lead up to the Reformation. Through their preaching, the Benedictines maintained regular contact and interaction with the laity and played an important part in their search for salvation. This study challenges us to rethink old narratives of late medieval monasticism as insular and irrelevant to wider society.