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Herbicides act as human-mediated novel selective agents and community disruptors, yet their full effects on eco-evolutionary dynamics in natural communities has only begun to be appreciated. Here we synthesize how herbicide exposures can result in dramatic phenotypic and compositional shifts within communities at the agro-ecological interface and how these in turn affect species interactions and drive plant (and plant-associates’) evolution in ways that can feedback to continue to affect the ecology and ecosystem functions of these assemblages. We advocate a holistic approach to understanding these dynamics that includes plastic changes and plant community transformations and also extends beyond this single trophic level targeted by herbicides to the effects on non-target plant-associated organisms and their potential to evolve, thereby embracing the complexity of these real-world systems. We make explicit recommendations for future research to achieve this goal and specifically address impacts of ecology on evolution, evolution on ecology, and their feedbacks so that we can gain a more predictive view of the fates of herbicide-impacted communities.