Carefully crafted descriptions of the public behavior of Sufis and depictions of how holy men ought to behave in the presence of rulers can be found in an eclectic body of literature penned in the 16th-17th century Egypt. These sources reflect complex and, oftentimes, conflicting collective recollections about the Sufis, holy men, and tariqas they seek to illuminate. A case in point is the literature we have on the Cairene Khalwati-Gulshanis. Whether penned by Ottomans or by Egyptians, commentaries on the Gulshanis have revised version of events. Gulshanis either suspiciously fit into proper channels of public behavior appearing as cordial supporters of political authority, pillars of piety, and bastions of social conformity, or they appear as controversial/heretical figures who engage in offensive public displays offending the members of the religious hierarchy—Ottoman and/or Egyptian. I argue here that there exists an inconsistent and unpredictable set of standards that determined who was a “pious and exemplary Sufi” in 16th century Egypt and that the formation(s) of this image hinged on how Sufis interacted with political authority. These standards were drawn by commentators who based their assumptions on ethnicity and sectarian identities that they sided with. However, the building blocks of these standards also depended closely on the relationship(s) of the Sufi(s) with political authority. I will explore the definitions of an “ideal Sufi” and demonstrate that Sufi figures—Khalwatis and otherwise—who were depicted as “epitomes of piety” were accepted as such only after their respective histories and actions proved to their audiences that they were socially (and politically) harmless figures. One of my goals here is to also show that in this environment, the Gulshanis represent an interesting case of contradictions when compared with their local Egyptian peers. Throughout their long history in Egypt, the Ottoman observers of Gulshanis regarded them as a “band apart” from their Misri and Rumi peers. Their Egyptian/ex-Mamluk commentators, on the other hand, didn’t necessarily depict them as such. For them, Gulshanis weren’t “exclusively” known for their heretical behaviors. To reach a nuanced understanding on who an “ideal Sufi” was, I will expand my analysis to those outside of the Khalwati and the Gulshani orbit and investigate how Cairene Sufis interacted with Mamluk and Ottoman rulers.