Limited knowledge exists regarding the yield response of soybean [Glycine max (L.) Merr.] from different maturity groups (MGs) to planting date in the southern United States. This information is needed to determine optimal planting dates for each MG. Our objective was to determine the optimum planting date for soybean in MG II, III, IV, and V in western Tennessee while considering producers’ risk preference. Net returns for each MG with four revenue protection (RP) insurance coverage levels were simulated using planting date–yield response functions for each MG. A multiyear experiment (2008–2010) was conducted on MG II, III, IV, and V planted at different dates in Milan, TN. The profit‐maximizing planting dates for soybean in western Tennessee were 24 May, 16 May, 13 May, and 22 May for MG II, III, IV, and V, respectively. The confidence intervals for the expected profit‐maximizing planting dates across MGs overlapped, suggesting that Tennessee producers have a long period for planting. Risk‐neutral to slightly risk‐averse producers would prefer MG III with no RP, but as the risk aversion increased, the preferred management strategy was MG III with 80% RP. These results will help producers determine optimum planting windows and crop insurance options for soybean production in West Tennessee based on their risk preferences.