Recent publications have underlined the importance of legal riddles (alghāz fiqhiyya) as a highly important genre of Islamic legal literature that had hitherto received no scholarly attention due to long established Eurocentric notions of what constitutes “serious” – as opposed to “playful” or “literary” – legal genres worthy of study. The work that has been done on this kind of literature in the past few years has demonstrated that collections of legal riddles played a central role in the writings of the four Sunni schools of law during the middle and modern periods and that these texts could not only serve to demonstrate legal erudition, facilitate legal learning, provide aesthetic entertainment, and generate intellectual enjoyment, but that they potentially also influenced processes of change in the legal culture of their time. To date, however, it has remained unclear how exactly collections of legal riddles were interconnected with and had a shaping influence on the legal culture of their time. This paper compares the collection of riddles al-Dhakhāʾir al-ashrafiyya fī alghāz al-ḥanafiyya by the Mamluk chief-judge of the Ḥanafī school ʿAbd al-Barr Ibn al-Shiḥna (d. 1515) to other texts including the legal views of this author in order to demonstrate that Ibn al-Shiḥna’s collection of legal riddles was a central element in the author’s strategy to bring about a closer alignment between the legal views of the Ḥanafī school and the Shāfiʿī madhhab at the expense of the other two Sunni schools of law recognized within the Mamluk Sultanate. The paper argues that Ibn al-Shiḥna used the genre of legal riddles, which has hitherto been misunderstood as a “playful” and “literary” and thus irrelevant type of legal writing, to bring about a shift in the power balance among the four major Sunni schools in the Mamluk realm. As a chief-judge with close contacts to the Mamluk ruler, Ibn al-Shiḥna was in a unique position to bring about this reconfiguration of the legal culture of this time by means of his writings across various legal genres, with legal riddles figuring particularly prominently in his strategy.