This paper is a thought piece about the intersection of law and literacy in the late medieval/early modern (15th-16th-century) eastern Mediterranean world—a geography deliberately intended to include both the Mamluks-then-Ottomans and Renaissance/Discovery Europe. In it, I will explore the concept of “legal literacy” as the intersection of literacy qua literacy and literacy as awareness of a legal cultural system and how to exploit it for personal and/or group benefit. I draw inspiration from Michael Clanchy’s notion of “practical literacy,” which he developed in the context of late medieval England (From Memory to Written Record: England 1066-1307). The paper extends from research on the Ottoman conquest of the Arabic-speaking world, which I performed using an array of legal sources (law codes, jurisprudential manuals, contract formularies, law court records, and endowment deeds) in both Arabic and Ottoman Turkish. This research has yielded evidence of the pervasive use of legal documents by large segments of the population, some of which would be conventionally considered illiterate. My basic contention is 1) that this period was not only one of geopolitical inflection (read: empire-building), but one in which we see a fundamental transition toward a new, popular relationship with writing itself, especially as connected to law, broadly conceived, and 2) that the expansion of writing and empire were mutually reinforcing if not always deliberately so. I will argue that in narrowly construing literacy as the ability to substantially read the written word, not only are other more ubiquitous forms of literacy missed, but the full power of being able to read even a very little is underestimated. I will conclude by engaging the slippery question of why the printing press took off in Europe while it did not appear in the Middle East until centuries later—this despite printing technology’s well-known Eastern origins and the Middle East’s/Islamic world’s early and sophisticated use of paper.