The question of whether one can define the parameters of a Sunni Muslim form of “orthodoxy” poses significant theoretical difficulties for researchers of the pre-modern world. Since the very notion of “orthodox” carries implications of power and control imposed from specific perspectives in given times and places, modern historians and social scientists rightly question whether the idea can serve any useful purpose in evaluating the historical trajectory of Muslim societies. However, intra-Muslim debates over these issues often impose themselves on scholarship regardless of these debates, both in earlier periods and the present. Ideas that might have seemed perfectly legitimate for Sunni thinkers of the late medieval and early modern world may look strange or unintelligible at best, and deviant at worst when evaluated in a more recent contemporary context. This paper aims to examine two such works and their authors, and attempt to evaluate how they fit into their own historical time and place as representative of Ottoman Sunnism. The first author, Cemal el-Halveti (d. 1499), was one of the founding figures of the Halveti order, first in its eastern frontier regions, and later in the Ottoman capital under Sultan Bayezid II. His relationship with the highest levels of political power, coupled with his descent from a well-regarded family of pious Muslim intellectuals, appear to make him an ironclad representative of the Sunni Muslim consensus of his time. Yet reading his most widely-circulated religious tract suggests that he was seeking to reinterpret basic elements of Sunni Muslim praxis along deeply esoteric and mystical lines. The second, Karabaş `Ali Veli (d. 1686), brought the Kastamonu-based Halveti branch of the Şa`baniyye order out of its provincial context and establishing it in Istanbul. But his most extensive work, a commentary on Ibn al-`Arabi entitled Kashf asrar al-fusus (“Unveiling of the secrets of the Fusus [al-hikam]”) and its abridgments, come across as almost unintelligible in a contemporary era, and there are signs that `Ali’s own followers and contemporaries questioned him as well. Ultimately, these case studies point toward a process of ongoing negotiations marked by generational changes and experimentation with different religious ideas within the context of Ottoman Sunnism.