Productivity of rainfed grain crops in Kentucky can be limited by water availability depending on precipitation patterns and the timing of critical crop developmental stages. Producers often need to address yield reductions due to water stress by increasing insurance costs, or compensate with years of greater yields. Adapting to earlier planting dates and/or different cultivar maturities could reduce the risk of yield losses due to water stress as well as increase yields under years of no water limitation. Moreover, developing site-specific diversification strategies or not putting all your eggs in the same basket could further reduce risk of yield losses and increase the overall farm net economic returns (i.e. planting 30% of acreage with a MG 3 cultivar in April, and the rest in May). Previous research in the U.S. Midsouth showed that soybean maturity group (MG) and planting date diversification strategies can greatly reduce risk of yield losses under irrigated conditions. The potential to increase productivity and yield stability under rainfed conditions in KY adapting to earlier planting dates or different MG cultivars, and by using diversifying management options, is expected to be much greater, but has not been quantified yet. This project will benefit soybean Kentucky farmers by generating yield responses across a wide range of planting dates and MG cultivars, and quantifying the yield limitation due to water stress. These are factors that play a major role in the determination of soybean yield on any given year and location, but that Kentucky farmers have currently limited information on. The outcomes from this project will provide site-specific management recommendations, as well as management diversification strategies that can increase economic returns under both rainfed and irrigated conditions.