Of all the groups of intellectuals of Islam in the Middle Periods, Sufis were among the most likely to contemplate themselves and the world around them, and to record their personal or collective life experiences. The dilemma posed by the conflict between the ego, the antagonist of the drama of mystical perfection, and the Divine eternity, in which Sufis aimed to drown themselves, notwithstanding, one finds scores of biographical notices in contemporary literature by and about Sufis. A significant deal of this material involves encounters with other Sufis including those occurring along the fault lines that mark the perceived boundaries of religious propriety. During the fifteenth century, a period of profound cultural creativity and one of inception of rigorously defined schools of piety, Sufis found themselves in increasing contact with fellow Sufis they would otherwise describe as deviant, and even, heretic. Sufis were frequent travelers and were typically wont to share spaces with fellow wayfarers; and the diversity and ambiguity of the political climate of the fifteenth century, unlike the next which witnessed the emergence of sectarian imperial politics, provided ample venues and opportunities of contact between various types of Sufis. The present study examines the intersection of the paths of Sufis of competing identities as reflected in contemporary biographical and autobiographical narratives. I am particularly interested in the accounts related to Zayn al-D?n al-Khw?f? (d. 1435), a shar??a-minded Sufi of Herat, and those of his disciples, who pursued to disseminate a normative piety that was conscious of the social and political balance of Islamdom. In their constant journeys for learning and instruction between places like Bukhara, Tabriz, Baghdad, Konya, and Cairo, these madrasa-educated “sober” Sufis shared rooms, private items, and books with other Sufis, “drunken” in behavior and “liberal” in discourse. How were these seemingly irreconcilable mystics so intimate? Why and how did their paths cross? What facilitated their cohabitation and what caused them to break up? Which subjects did they agree upon and which were divisive? How did these Sufis characterize these experiences? More importantly, what do these confrontations and the proceeding narrations mean for the history of culture and politics in the period? To conclude briefly, this study aims to contribute to the cultural history of the fifteenth century by shedding light on these aspects of the development of communal Sufism as regards the transformation of the political order in Islamdom.