Controlling crop pests while conserving pollinators is challenging, particularly when prophylactically applying broad-spectrum, systemic insecticides such as neonicotinoids. Systemic insecticides are often used in conventional agriculture in commercial settings, but the conditions that optimally balance pest management and pollination are poorly understood. We investigated how insecticide application strategies control pests and expose pollinators to insecticides with an observational study of cucurbit crops in the Midwestern United States. To define the window of protection and potential pollinator exposure resulting from alternative insecticide application strategies, we surveyed 62 farms cultivating cucumber, watermelon, or pumpkin across 2 yr. We evaluated insecticide regimes, abundance of striped and spotted cucumber beetles (Acalymma vittatum [Fabricius] and Diabrotica undecimpunctata Mannerheim), and insecticide residues in leaves, pollen, and nectar. We found that growers used neonicotinoids (thiamethoxam and imidacloprid) at planting in all cucumber and pumpkin and approximately half of watermelon farms. In cucumber, foliar thiamethoxam levels were orders of magnitude higher than the other crops, excluding nearly all beetles from fields. In watermelon and pumpkin, neonicotinoids applied at planting resulted in 4-8wk of protection before beetle populations increased. Floral insecticide concentrations correlated strongly with foliar concentrations across all crops, resulting in high potential exposure to pollinators in cucumber and low-moderate exposure in pumpkin and watermelon. Thus, the highest-input insecticide regimes maintained cucumber beetles far below economic thresholds while also exposing pollinators to the highest pollen and nectar insecticide concentrations. In cucurbits, reducing pesticide inputs will likely better balance crop protection and pollination, reduce costs, and improve yields.