We present a spatial interaction entropy maximizing and structural dynamics model of settlements from the Middle Bronze (MBA) and Iron Ages (IA) in the Khabur Triangle (KT) region within Syria. The model addresses factors that make locations attractive for trade and settlement, affecting settlement growth and change. We explore why some sites become relatively major settlements, while others diminish in the periods discussed. We assess how political and geographic constraints affect regional settlement transformations, while also accounting for uncertainty in the archaeological data. Model outputs indicate how the MBA settlement pattern contrasts from the IA for the same region when different factors affecting settlement size importance, facility of movement, and exogenous site interactions are studied. The results suggest the importance of political and historical factors in these periods and also demonstrate the value of a quantitative model in explaining emergent settlement size distributions across landscapes affected by different socio-environmental causal elements.