A cereal rye cover crop mulch can suppress summer annual weeds early in the soybean growing season. However, a multi-tactic weed management approach is required when annual weed seedbanks are large or perennial weeds are present. In such situations, the weed suppression from a cereal rye mulch can be supplemented with the use of high-residue cultivators which can prolong the weed-free period during soybean growth. Research trials were conducted to determine the optimum timing of high-residue cultivation for weed control in rolled-crimped cereal rye mulches. Treatments included three cultivation timings with a high-residue cultivator: early (3-4 wk after soybean planting (WAP)), intermediate (5-6 WAP), and late (7-8 WAP), a weed-free and no-cultivation control. Crop and weed measurement included cereal rye biomass, weed biomass, soybean population and biomass, and yield. Cereal rye biomass was 50% lower and weed biomass was three times greater in 2011 than in 2010 and 2012 due to 2011 being a dry year. There was no significant effect of cultivation timing on soybean population when compared to no-cultivation or hand-weeded treatments. While cultivation reduced weed biomass by 67% compared to no-cultivation, soybean yield was only improved by 12% in early and late cultivation treatments and 22% in intermediate cultivation treatment when compared to no-cultivation. Effective strategies for improving weed management by integrating the use of a high-residue cultivator in no-till organic systems could help existing organic field crop producers to reduce tillage while also encourage adoption of organic crop production by conventional growers who prefer reduced-tillage systems. Unlike traditional organic cultivation equipment, therefore, optimal timing of cultivation should be delayed several weeks in organic cover crop-based no-till planted soybean production as compared to the typical tillage-based approach to ensure both weed control and optimal yield.