Natural systems contain diverse assemblages of plants, providing a matrix of potential hosts that herbivores must navigate. Insect-plant host choice patterns are crucial to understanding both herbivore outbreaks and the consequences of outbreaks for plant hosts. Here, I follow the 2021 Brood X periodical cicada mass emergence event in the BiodiversiTREE forest diversity experiment at the Smithsonian Environmental Research Center (SERC) in Edgewater, MD, to uncover whether tree diversity influences cicada oviposition preferences or tree responses to oviposition (flagging), for 15 tree species grown in plots of single species or 12-species mixtures. While cicadas demonstrate clear tree species preferences, the diversity of the surrounding tree neighborhood plays at least as important a role in determining oviposition preference and tree flagging responses. Cicadas were threefold more likely to oviposit in trees grown in single species vs. mixed species plots. While overall, I find a concomitant decrease in tree flagging in diverse plots. I also document that species flag at different rates in response to the same oviposition scar density. Even when accounting for differential oviposition rates, surrounding tree diversity remains an essential additional predictor of tree flagging responses with trees in diverse plots less likely to flag at the same density of scars, suggesting a differential capacity of trees to tolerate damage when growing in single species plots. This study creates a richer understanding of the importance of tree context, specifically surrounding tree diversity, in shaping the ecological ramifications of a mass insect emergence event.