Sorghum is an important food and feed crop in the dry lowland areas of Ethiopia. Farmers grow both early-sown long-duration landraces and late-sown short-duration improved varieties. Because timing and intensity of drought stress can vary in space and time, an understanding of major traits (G), environments (E), management (M), and their interactions (G×E×M) is needed to optimize grain and forage yield given the limited available resources. Crop simulation modeling can provide insights into these complex G×E×M interactions and be used to identify possible avenues for adaptation to prevalent drought patterns in Ethiopia. In a previous study predictive phenology models were developed for a range of Ethiopian germplasm. In this study, the aims were to (1) further parameterize and validate the APSIM-sorghum model for crop growth and yield of Ethiopian germplasm, and (2) quantify by simulation the productivity-risk trade-offs associated with early vs late sowing strategies in the dry lowlands of Ethiopia. Field experiments involving Ethiopian germplasm with contrasting phenology and height were conducted under well-watered (Melkassa) and water-limited (Miesso) conditions and crop development, growth and yield measured. Soil characterization and weather records at the experimental sites, combined with model parameterization, enabled testing of the APSIM-sorghum model, which showed good correspondence between simulated and observed data. The simulated productivity for the Ethiopian dry lowlands environments showed trade-offs between biomass and grain yield for early and late sowing strategies. The late sowing strategy tended to produce less biomass except in poor seasons, whereas it tended to produce greater grain yield except in very good seasons. This study exemplified the systems approach to identifying traits and management options needed to quantify the production-risk trade-offs associated with crop adaptation in the Ethiopian dry lowlands and further exemplifies the general robustness of the sorghum model in APSIM for this task.