One of the hallmarks of the Arabic literature of the Mamluk era is the very frequent use of semantic ambiguity, a rhetorical tool that saw its final theorisation in this period and the emergence of the canonical form that still appears in rhetorical treatises today: tawriya. After the 1966 publication of Bonebakkers study on tawriya, few steps have been taken to further our understanding of tawriyas use in literary practice. Thus, this book investigates two deeper aspects of the art. First, it studies the sources that contributed to the theorisation of semantic ambiguity. Second, it puts theory to the test with a philological and semiotic approach that reveals the readers role in the aesthetic success of literary works involving tawriya.