Scholarship describes both the Early Bronze Age and the Middle Bronze Age in the southern Levant as “urban” eras, yet, beyond broad superficial similarities, the pattern of settlement and subsequent urban character of each period differs widely. Rather than assume that this precludes examining the two eras together, however, these differences instead raise questions about the variables and factors that influenced and affected settlement in the Bronze Age and the subsequent development of “urban” society in each era. Urban development affects all aspects of a society, and is revealed through the organization, size, and distribution of settlement throughout a region; consequently, the subsequent growth and sustainability of any urban society then hinges on the strength and stability of that settlement. Broad-scale and long-term examination of settlement patterns in the southern Levant reveals important differences between the Early and Middle Bronze Ages that have significant ramifications regarding the nature of urban society in each era. This paper will present data and analysis of settlement patterns in both the Early and Middle Bronze Age southern Levant and address how these patterns reflect the strength, organization, and stability of urban development in each era.