Soybean accounts from more than half of the acres dedicated to row crop production in the mid-south, leading to a wide planting window from late-March through mid-July. Studies were conducted in 2013 and 2014 evaluating seven planting dates of soybean, and their impact on agronomics. As planting was delayed, plant heights significantly increased, increasing the potential for lodging. Canopy closure significantly decreased as planting was delayed, leaving soybean more vulnerable to caterpillar pests. Yield potential also significantly decreased as planting was delayed. Season long surveys of insect pests and their arthropod natural enemies were conducted from 2013 to 2014 in small plot studies, and in large plot studies from 2015 to 2016 across multiple planting dates. The most common insect pests encountered in both studies were bean leaf beetles, the stink bug complex, and soybean looper. The most common natural enemies encountered were lady beetles, spiders, and the assassin bug complex. In general, insect pests densities increased as planting was delayed, whereas natural enemies were higher in earlier plantings or had no change throughout the planting windows. With the increased difficulty of controlling some caterpillar pests such as soybean looper, new control tactics need to be evaluated. A simulated Bt treatment was evaluated against a threshold, bug only, and untreated control across multiple plantings in 2013 and 2014. The simulated Bt treatment yielded significantly higher than the untreated control at plantings from early-June through mid-July. These were the only plantings that reached action threshold for soybean looper. The simulated Bt and threshold treatments were not significantly different from one another. In 2015 and 2016, a simulated Bt treatment plus threshold was evaluated in a late planting situation. The simulated Bt plus threshold treatment yielded significantly higher than the untreated control at the early-June and early-July plantings. Also in 2015 and 2016, the simulated Bt treatment was evaluated against a grower check on producer fields at 23 locations. The simulated Bt treatment resulted in significantly higher soybean yields than the grower check.