Harvest weed seed controls (HWSC) destroy weed seeds that are retained by the plant at crop harvest, which would typically be spread by the harvester along with other field residues. HWSC exploits coincidental maturity between crops and weeds, so an experiment was designed to collect weed seeds as they shatter throughout the growing season and through a simulated harvest delay. This experiment monitored four economically important broadleaf species and two grass species in a soybean (Glycine max (L.) Merr.) field. Results indicated that broadleaf species shattered seed at rates accelerating through the growing season, while grass species shattered more seed early in the growing season. Field experiments in organic and conventional winter wheat (Triticum aestivum L.) fields infested with Italian ryegrass (Lolium perenne L. ssp. multiflorum (Lam.) Husnot) compared two HWSC techniques to grower-standard weed management programs in each system, including both no-till and full-till standard treatments in the conventional system. Italian ryegrass populations were monitored, and wheat yield was measured both before and after HWSC application. In both organic and conventional cropping systems, HWSC treatments did not provide better Italian ryegrass control than the grower-standard treatments. The conventional program including tillage boosted Italian ryegrass populations. These results suggest that HWSC treatments did not enhance Italian ryegrass control compared to grower-standard practices in either the organic or conventional systems. Additionally, broadleaf weeds may retain enough seeds to be viable targets for HWSC. Incorporating best practices, such as a timely crop harvest, is key for understanding and optimizing HWSC.