Scholarship on the Red Sea in the post-Classical period has traditionally focused on the India trade, which was revitalized under the Fatimids and Ayyubids beginning in the 11th and 12th centuries. By the 13th century the Red Sea was the hub of a widespread international network, leading Janet Abu-Lughod to propose the beginnings of a World System economy. This thriving economic system, however, did not appear out of nowhere. Instead, it represents the expansion of earlier trading networks in the region. Several scholars have recently proposed the presence of significant maritime activity in the Red Sea prior to the 11th century. Timothy Power has argued that the rediscovery of the ancient gold mines of northeastern Africa resulted in a 9th – 10th century Arab “gold rush” into the Sudan and a subsequent boom in the slave trade. Kristoffer Damgaard dates the expansion of maritime trade to the later 8th and early 9th centuries based on the appearance of new ceramic forms from Iraq and China. This paper will push the timeline for maritime intensification back further, proposing that the roots of these later mercantile networks were founded under the Rashidun and Umayyad caliphs. The importance of this period has largely been overlooked due to the paucity of literary and archaeological data. However, a close survey of the available material reveals evidence for expanding connectivity and resource development, including the rise of state-sponsored grain export, the intensification of agriculture and mining around the Red Sea periphery, and the establishment of new ports. These case studies will demonstrate how the consistent movement of ‘non-luxury’ goods created persistent maritime pathways. This paper will draw parallels with the Roman annona (state-sponsored grain trade), which stimulated economic exchange and helped define trade routes in the Mediterranean by establishing regular shipping patterns. This study will demonstrate that the maritime connections arising from these early economic phenomena laid the groundwork for an integrated network in the Red Sea basin. Ultimately, this network gave rise to a "commercial crescent" – an economic region that, through burgeoning commerce and exchange, would stimulate the growth of coastal communities and trade within the Red Sea, Indian Ocean, and Persian Gulf.