My project aims to extend recent scholarship on the sociocultural and intellectual landscape of medieval Kerala by interrogating mathematical and astronomical texts and manuals produced in the region in the late medieval period, as well as vernacular historical accounts that have not so far been included in the conversation, towards reconstructing a fuller history of Kerala’s mathematical tradition. The study of secondary mathematical literature in Malayalam is warranted not merely on its own terms, but also aids in the larger comparative project of articulating and evaluating markers of mathematical, and broadly scientific, literacy across regions, especially in South India. With its emphasis on occupational practice, my project proposes an alternative approach by which to delineate the complex and mutually reciprocal methods of knowing through which multiple scholars, invested in the process of knowledge making, navigated fixed and fluid social boundaries as they contributed to extending the boundaries of knowledge.