Holy fools for Christ’s sake position themselves as sinners, yet in Eastern Orthodox tradition they are canonical saints and enjoy a high regard as miracle-workers, visionaries and prophets. However, at the time of inception of the concept and behavioral model of holy foolishness, its representatives did not have much to do with visions, otherworldly travels or numinous dimension in general. Initially holy fools were ascetics and only later on they acquired the status of visionaries and prophets. In this regard there is an insuperable gap between the silent Nun Who Feigned Madness from Palladius’ Lausaic History (V c.) and Leontius’ clairvoyant, telepathic Symeon of Emesa (VII c.), between Palladius’ Serapion (V c.) and Nikiphoros’ visionary, Andrew the Fool of Constantinople (X c.). In my talk I will ponder the quantum leap of the holy fool’s transformation from an ascetic to a visionary as I will explore early Byzantine textualizations of holy foolishness.