Herbicide resistance, documented in many economically damaging weed species, is a major threat to global crop production. The injudicious use of herbicides, often in the absence of diverse weed control strategies, poses an immense selection pressure on weed communities for resistance evolution and weed adaptive traits such as high seed dormancy. This study evaluates the interaction among developing herbicide resistance, seed size, and seed dormancy of ripgut brome (Bromus diandrus Roth), wild oat (Avena fatua L.), and hare barley [Hordeum leporinum Link; syn. Hordeum murinum L. ssp. leporinum (Link) Arcang.] collected from within intensively managed fields (in-crop) in comparison with populations in surrounding ruderal (non-crop disturbed) areas with no history of exposure to herbicides within the Western Australian grainbelt. Seed size of the three species varied by farming system (continuous cereal-intensive annual crops, diverse annual crops, pasture based) and habitat (in-crop, ruderal). Field populations of H. leporinum and B. diandrus tended to have greater seed size compared with ruderal populations. Larger seeds had significantly more dormancy in all three weed species. Field-collected populations that were exposed to herbicide applications for at least the past 5 yr exhibited significantly greater seed dormancy compared with their counterparts present in ruderal areas within the same geographic area. The association between increased seed dormancy and developing multiple herbicide resistance further complicates effective weed management.