This article investigates Matilda’s friendship with Archbishop Anselm of Canterbury. It presents and analyzes new evidence of Matilda's role during Anselm of Canterbury’s first and second exiles and explores the political, social, and ideological implications of Anselm of Canterbury and Matilda’s relationship in depth. The article suggests that the countess may have impacted Anselm of Canterbury’s notion of Libertas Ecclesia. It considers the spiritual friendship between the archbishop of Canterbury and Matilda, re-examining the extant sources and evaluates a new, wide variety of data – mainly their letters, Anselm of Canterbury’s devotional writing, and the Admont illuminated manuscript of Anselm of Canterbury’s Prayers and Meditations. These sources allow us to uncover new aspects of the intense familiarity between the saint and the countess and, disclosing new personal elements of their spirituality and devotional piety, clarify the nature and scope of the relationship.