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(1) Background: <i>Eragrostis plana</i> Ness is a invasive C₄ perennial grass in South America and very adaptable to environmental stresses. Our hypothesis is that there is a transgenerational cross-talk between environmental stresses and weed response to herbicides. This study’s objectives were to: (1) evaluate if <i>E. plana</i> primed by drought stress (DRY), a sub-lethal dose of quizalofop-p-ethyl (QPE), or a combination of both drought and herbicide stresses (DRY × QPE), produce a progeny with decreased sensitivity to quizalofop and (2) investigate the potential mechanisms involved in this adaptation; (2) Methods: A population of <i>E. plana</i> was isolatedly submitted to treatments for drought, quizalofop or drought plus quizalofop for two generations. The progenies were analyzed for sensitivity to the herbicide quizalofop and performed biochemical, chromatographic and molecular analyses.; (3) Results: In the G₂ generation, the quizalofop-treated CHK population had reduced stomatal conductance and increased hydrogen peroxide and lipid peroxidation. On the other hand, there was no change in stomatal conductance, hydrogen peroxide level, and lipid peroxidation in the quizalofop-treated DRY population. In addition, this population had increased antioxidant enzyme activity and upregulated <i>CYP72A31</i> and <i>CYP81A12</i> expression, which was accompanied by reduced quizalofop-p-ethyl concentrations; (4) Conclusions: <i>E. plana</i> demonstrated a capacity for transgenerational adaptation to abiotic stresses, with the population exposed to drought stress (DRY) becoming less sensitive to quizalofop-p-ethyl treatment.