Amid widespread occurrence of herbicide-resistant weeds in the United States, the use of PRE herbicides and cover crops have resurged once again as important strategies for weed management in cropping systems. The objective of this experiment was to evaluate the length of soil residual weed control from PRE soybean herbicides and the detrimental impact of these herbicides on cover crop species using field treated soil in greenhouse bioassays. Greenhouse bioassays were conducted using soil from field experiments conducted in 2018 and 2019 in Arlington and Lancaster, WI. PRE herbicides consisted of imazethapyr, chlorimuron-ethyl, and cloransulam-methyl (acetolactate synthase [ALS] inhibitors); metribuzin (photosystem II [PS II] inhibitor); sulfentrazone, flumioxazin, and saflufenacil (protoporphyrinogen oxidase [PPO] inhibitors); acetochlor, S-metolachlor, dimethenamid-P, and pyroxasulfone (very long-chain fatty acid [VLCFA] inhibitors); and a nontreated control. Greenhouse bioassays were conducted using soil (depth, 0 to 10 cm) sampled at 0, 10, 20, 30, 40, and 50 d after treatment (DAT). Palmer amaranth and giant foxtail (weeds), and radish and cereal rye (cover crops) were used as bioindicators of herbicide levels in the soil. Bioassay results showed extended soil residual control of Palmer amaranth with sulfentrazone and pyroxasulfone; extended residual control of giant foxtail was observed with pyroxasulfone and S-metolachlor. Chlorimuron-ethyl and metribuzin were the most injurious herbicides to radish and cereal rye shortly after application, respectively, but minimal injury was observed from soil samples collected 50 DAT, indicating the use of PRE and fall-seeded cover crops in southern Wisconsin can be compatible. These results can support growers and practitioners with selection of effective PRE herbicides for Palmer amaranth and giant foxtail control and reduced impact on fall-seeded radish and cereal rye cover crops, altogether leading to more effective, diverse, and sustainable weed management programs.