The order and timing of species arrival can significantly influence community assembly and ecological dynamics. This phenomenon is particularly relevant in plant-insect interactions, where early-arriving herbivores can shape subsequent interactions with other arthropods through both direct and indirect mechanisms. Over multiple years, I investigated how the presence and behavior of an early-season insect pest, the striped cucumber beetle (Acalymma vittatum), affected the behavior and success of a later-season herbivore (Anasa tristis) and its parasitoid natural enemy (Celatoria setosa). My research aimed to understand how interactions between A. vittatum and other arthropods occurred, what mechanisms underpinned these interactions, and the downstream consequences for all species involved. To answer this question, I specifically tested 1) How the presence of A. vittatum cues, such as foliar damage and vittatalactone – male aggregation pheromone – influenced attraction of A. tristis and C. setosa? 2) How early-season seedling damage by A. vittatum affects A. tristis growth and overall plant performance through changes in plant quality? 3) How defensive plant compounds sequestered by A. vittatum hosts influence C. setosa success and development? 4) How interactions between A. vittatum and A. tristis, or between A. vittatum and C. setosa, impact the performance of A. vittatum itself. Overall, I show that A. vittatum colonization attracted and facilitated A. tristis and led to reductions in reproductive traits and crop yield in cultivated Cucurbita pepo varieties. In interactions between A. vittatum and C. setosa, I observed asymmetries in parasitoid foraging behavior, host preference, and parasitism success. Despite these complexities, C. setosa proved to be an effective biological control agent, achieving high parasitism rates and reducing pest performance through both consumptive and non-consumptive effects, including decreased survival, feeding, oviposition, and vittatalactone emission in A. vittatum. Overall, my work highlights the behavioral dynamics within an insect community and shows that the natural sequence of herbivore arrival can have lasting impacts on plant reproductive traits and late-season performance.