Preplant (PP) herbicide applications are an important tool within an integrated weed management system, specifically in no-till production. An understanding of crop tolerance regarding PP applications is important for effectively integrating a new herbicide into no-till cropping systems. Twelve field trials (six in corn and six in soybean) were conducted over a 2-yr period (2018 and 2019) near Exeter and Ridgetown, ON. The purpose of these studies was to evaluate the tolerance of soybean and corn to halauxifen-methyl applied PP, PRE, or POST at the registered rate (5 g a.i. ha−1) and twice the registered rate (10 g a.i. ha−1), hereafter referred to as the 1× and 2× rate, respectively. All trials were kept weed-free throughout the growing season to remove the confounding effect of weed interference. Halauxifen-methyl applied 14 d preplant (DPP), 7 DPP, 1 DPP, and 5 d after seeding (DAS) at the 1× and 2× rates caused ≤10% visible soybean injury. In contrast, halauxifen-methyl applied POST (cotyledon–unifoliate stage, VE-VC) caused 67% to 87% visible soybean injury, a 50% to 53% reduction in height, 65% to 81% decrease in population, 56% to 67% lower biomass, and 53% to 63% decline in yield. Halauxifen-methyl applied 10 DPP, 5 DPP, 1 DPP, 5 DAS, and POST (spike–one leaf stage, VE-V1) at the 1× and 2× rate caused ≤3% visible corn injury and caused no effect on corn height or biomass. Halauxifen-methyl applied at VE-V1 at the 2× rate reduced corn yield 10%. Based on these studies, the current application restriction of 7 DPP in soybean and 5 DPP in corn is conservative and could be expanded. Expanding the application window of halauxifen-methyl would increase the utility of this herbicide for producers.