Today, scholarship on Islamic mysticism mostly prioritizes the poetry and mystical teachings of famous Sufi masters, with limited efforts to historically contextualize them. One of the sub-branches of the Halvet order, the Gleniye, while being an influential participant in early modern Ottoman politics and society, presents the historian of Sufism with a rare opportunity to approach this gap. Despite offering a wide range of untapped literary, hagiographical, and historical sources, studies on the Gleniye remain in the margins. Through Gleniye literary production, including poetry and hagio-biographies by dervish-authors, this article explores the mystical thought and piety of brhm-i Gleni (d. 940/1534), the founder of the Glen order of dervishes in Egypt. Close textual analysis of sources reveals that Glens inspirations formed the contours of the orders early literature and culture. I argue that the Gleniye literary corpus, and the culture formed alongside it, was a product of changing socio-political environments, not a replica of the doctrines of the orders founder. The shifts in the corpus unveil the orders changing practical priorities and shed light on how the Gleniye secured a stable niche for itself in Ottoman Egypt in the sixteenth century.