Some of the most politically and culturally significant cities in first millennium BC northern Mesopotamia were located in agriculturally marginal landscapes. In order to sustain these settlements, variant cultivation techniques were practiced by local populations. Understanding the dynamics and implications of crop management practices requires that socio-ecological variables be addressed over recurrent crop cycles. This paper employs a coupled socio-ecological modeling approach that enables interactions between a quantitative environmental model and an agent-based social model by using the ENKIMDU simulation tool. The reconstructed landscape near the ancient city of Assur is used as the example setting to test the effectiveness of simulated cultivation strategies. These methods include sole dependence on biennial fallow and rainfall, gravity flow irrigation, application of manure, and the integration of all these approaches. Results obtained within ENKIMDU attempt to delineate agricultural constraints and potential benefits of the specific anthropogenic processes and strategies addressed.