The beginning of the Middle Bronze Age (MB IIA) in Canaan (ca. 1950-1740 B.C.E.) set the stage for many of the cultural, political, and economic institutions that shaped the ancient Near East. Particular theoretical models for the analysis of complex societies are used in this study to examine textual, pictorial, and archaeological evidence relating to the nature and organization of MB IIA Canaan. The written and pictorial evidence pertaining to Egyptian-Canaanite contact indicates a fluid relationship that changed over time in response to changing social, political, and economic developments in both cultures. As a result, Egyptian policy toward Canaan was multifaceted, including approaches ranging from the use of military force to magical rites. The analysis of MB IIA site-distribution indicates that Canaanite settlement first developed in areas on the coast most conducive to agricultural growth. It then progressed according to a dendritic pattern of organization along the east-west wadi systems into the interior in response to a growing demand for resources and raw materials, fueled in part by contact with Egypt and the international world of the eastern Mediterranean. Chronological correlations between the Canaanite settlement systems and Middle Kingdom Egypt also indicate that the beginning of the MB IIA in Canaan dates well into the Middle Kingdom, rather than being contemporary with its beginnings, as previously understood. Findings concerning the Canaanite-Egyptian relationship, Canaanite site-distribution, and chronological connections between these two regions all illustrate the development of Canaan from a society in the first stages of urbanization to a fully urbanized one, setting the stage for the rise of the Hyksos to power in Egypt.