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Distinct survival strategies can result from trade-offs in plant function under contrasting environments. Investment in drought resistance mechanisms can enhance survivorship but result in conservative growth. We tested the hypothesis that the widespread oaks (Quercus spp.) of the Americas exhibit an interspecific trade-off between drought resistance and growth capacity. Using experimental water treatments, we isolated adaptive trait associations among species in relation to their broad climates of origin and tested for correlated evolution between plant functional responses to water availability and habitat. Across all lineages, oaks displayed plastic drought responses - typically acclimating through osmolyte accumulation in leaves and/or employing conservative growth. Oaks from xeric climates had higher osmolytes and reduced stomatal pore area index, which allows for moderated gas exchange and limits tissue loss. Patterns suggest drought resistance strategies are convergent and under strong adaptive pressure. Leaf habit, however, mediates the growth and drought resistance strategies of oaks. Deciduous species, and evergreen species from xeric climates, have increased drought tolerance through osmoregulation, which allows for continuous, conservative growth. Evergreen mesic species show limited drought resistance but could enhance growth under well-watered conditions. Consequently, evergreen species from mesic environments are especially vulnerable to chronic drought and climate change., (© 2023 The Authors. New Phytologist © 2023 New Phytologist Foundation.)