Foliar-applied postemergence herbicides are a critical component of corn (Zea mays L.) and soybean [Glycine max (L.) Merr.] weed management programs in North America. Rainfall and air temperature around the time of application may affect the efficacy of herbicides applied postemergence in corn or soybean production fields. However, previous research utilized a limited number of site-years and may not capture the range of rainfall and air temperatures that these herbicides are exposed to throughout North America. The objective of this research was to model the probability of achieving successful weed control (≥85%) with commonly applied postemergence herbicides across a broad range of environments. A large database of more than 10,000 individual herbicide evaluation field trials conducted throughout North America was used in this study. The database was filtered to include only trials with a single postemergence application of fomesafen, glyphosate, mesotrione, or fomesafen + glyphosate. Waterhemp [Amaranthus tuberculatus (Moq.) Sauer], morningglory species (Ipomoea spp.), and giant foxtail (Setaria faberi Herrm.) were the weeds of focus. Separate random forest models were created for each weed species by herbicide combination. The probability of successful weed control deteriorated when the average air temperature within the first 10 d after application was <19 or >25 C for most of the herbicide by weed species models. Additionally, drier conditions before postemergence herbicide application reduced the probability of successful control for several of the herbicide by weed species models. As air temperatures increase and rainfall becomes more variable, weed control with many of the commonly used postemergence herbicides is likely to become less reliable.