This article provides a close reading of Shihāb al-Dīn al-Khafājī’s (d. 1069/1659) Maqāma Rūmiyya, a narrative work detailing the journey of an Arab scholar to Istanbul who then satirizes his Rūmī counterparts in acerbic fashion. Despite its notoriety, the cursory scholarly attention paid to the text has either merely observed the maqāma’s departure from the genre’s classical structure or mentioned its immediate context, al-Khafājī’s dispute with the Grand Mufti in Istanbul. Firstly, I demonstrate that the text is a deeply layered adab work, one highly referential of and intertextual with the Arabic literary tradition, which aims not only at satirical entertainment but also at serious moral import. Secondly, I assert that al-Khafājī loosely utilized the maqāma genre to express personal anxieties over imperial politics and cultural difference. I consider how al-Khafājī’s digressive sections on generosity and rulership get at the core of what really concerns him: sociability among learned Muslims.