The relationship between Sufis and ruling elites can be best described as ‘complicated.’ A common trope one can find in Sufi writings is the author’s emphasis on maintaining a safe distance between oneself and the wealthy and influential patron, for fear that the relationship to the latter corrupts the morals of the former. A closer look at Islamic history nevertheless reveals that, whether as friends or foes, influential Sufis were rarely too far from the ruler’s court. As interpreters of the sovereign’s dreams, spiritual guides, or companions in battle, Sufi shaykhs enjoyed a close, and oftentimes fraught relationship to political power. This paper will focus on an aspect of this historical relationship between Sufis and rulers that is yet to receive scholarly attention: Ottoman ‘army shaykhs.’ ‘Army shaykhs’ (ordu şeyhleri) were Sufis who accompanied Ottoman rulers to the battlefield and appear to have been typically tasked with uplifting the morale of the troops. I will focus on two of the earliest recorded examples we have of such Sufi involvement in Ottoman military campaigns: Akşemseddin (d. 863/1459), the Sufi who advised Sultan Mehmed the Conqueror and was instrumental in the conquest of Constantinople in 1453, and Nureddinzade Müslihuddin (d. 981/1574), whose dream and advice guided Sultan Süleyman on his campaign to Szigetvar in 1566. I argue that the roles Sufis had in military campaigns – as gleaned from chronicles and biographical sources – both complicate scholarly categories of Sufism as apolitical and shed light on the uneasy nature of the Sufi-Sultan dynamics in the Ottoman historical context and beyond.