Abstract One of the most characteristic and resilient elements of state documents promulgated by the chancelleries of medieval and early modern Turkic Islamic empires is the toghrā, or calligraphic signature of rulers. In the administrative history of Iran, the chessboard toghrā constitutes a short and lesser-known variant. This royal emblem appeared during the Safavid period as the result of several administrative reforms. In this paper, I outline the development of the toghrā in medieval Iran on the basis of surviving documents and fragments and then offer a detailed portrait of the birth and brief life of the chessboard toghrā. Furthermore, the conspicuous similarity between this form and the toghrās of Mughal emperors precipitates a comparison and close analysis of their different elements and characteristics. Drawing on both published and unpublished royal decrees, this article explores the possible dimension of interrelation and provides insights into their similarities and differences in use and content.