In dialogue with new historiographical references and interpretative approaches to the History of Education in the Middle Ages, our intention in this article is understand the meaning of obedience and its tensions in monastic environments and in thone connected to urban cathedrals between the final decades of the 11th century and and the early 12th century. Therefore, we believe to be possible access the means behind these daily actions in the education of young people which seem to indicate not the merely existence of breaks or questioning of the prevailing powers that would announce the emergency of something new as was imagined for so long, but rather the creation of new personal relationships connected to increased access options to new masters then offering their knowledge and a student mobility uncommon until the 12th century. Thus, based on passages found in the epistolaries of John of Salisbury (c.1120-1180), Anselm of Canterbury (c.1033-1109) and Bernard of Clairvaux (1090-1153), among other sources, our aim is to shed light on these tensions in the hope of better seeing the feasible protagonism of those still seeking leaning and what their characteristics were, mainly in times of great and profound transformations like the 12th century.