The appearance of the brailed rig and loose–footed sail at the end of the Late Bronze Age revolutionized seafaring in the eastern Mediterranean. The most famous early appearance of this new technology is found in history’s first visual representation of a naval battle, on the walls of Ramesses III’s mortuary temple at Medinet Habu. In this monumental combat scene, both Egyptian and Sea Peoples ships are depicted with this new rig, as well as top–mounted crow’s nests and decking upon which shipborne warriors do battle. The identical employment of these innovative components of maritime technology by opposing forces in this battle suggests either some level of previous contact between the invaders and those responsible for designing and constructing Egypt’s ships of war, or shared interaction with a third party, perhaps on the Syro–Canaanite coast. This article examines the evidence for the development of the brailed rig in the eastern Mediterranean, and explores the possibility that at least one group of Sea Peoples, who may have comprised a key part of the international economy of the Late Bronze Age in their role as “pirates, raiders, and traders” (Georgiou 2012: 527) – Artzy’s “nomads of the sea” (1997) – played a similarly integral role in the transference of maritime technology between the Levant, Egypt, and the Aegean.