Sinan’s Ambivalence: The Triangular Design of the Süleymanıye Schools Complex in Istanbul interrogates the anomalous configuration of the Süleymanıye schools, including the unorthodox angular Dar-ul-Hadith, the largest and most important Ottoman educational institution, designed by the great Ottoman master-builder Sinan in 1548–59. The Süleymanıye, as Yasir Mohammad Sakr demonstrates, is not a mere adaptation of preexisting symmetrical school models to contextual contingencies, as historians have contended. Rather, the Süleymanıye and its seeming anomalies are a function of the architect’s own relentless retrospection, repeatedly reinterpreting and opposing the very types that he initially created during the same design process. Sinan synthesized the idealized Ottoman planning patterns with a vigorous fragmentation and dispersal of its functional and symbolic elements to create an innovative hybrid typology for the Süleymanıye schools, especially the Dar-ul-Hadith. The study concludes that the triangular Dar-ul-Hadith is not a residual, ad hoc space as commonly perceived. It is the key to formulating the Süleymanıye master plan, which the author defines as a powerful symbolic scheme monumentalizing the new social arrangement by Sinan’s patron, Süleyman the Magnificent. Thus, far from the negative association usually attached to the notion of “ambivalence,” Sinan’s design practice presents it as a viable alternative approach for the history of Ottoman architecture.