Organisms that move across ecosystem boundaries connect food webs in apparently disparate locations. As part of their life cycle, aquatic insects transition from aquatic larvae to terrestrial adults, thereby linking freshwater ecosystem processes and terrestrial insectivore dynamics. These linkages are strongly affected by contamination of freshwater ecosystems, which can reduce production of adult aquatic insects (i.e., emergence), increase contaminant concentrations in adult insect tissues, and alter contaminant flux to terrestrial ecosystems. Despite the potential impact of contaminants on adult aquatic insects, little is known about predicting these effects. Here, I develop a heuristic model based on contaminant properties and ecotoxicological principles to predict the effects of various classes of aquatic contaminants on adult aquatic insects and discuss implications for terrestrial insectivores living near contaminated freshwaters. The main finding is that contaminant classes vary greatly in how their biologically-mediated effects on aquatic insects affect terrestrial insectivores. Highly bioaccumulative contaminants that are well retained during metamorphosis, like polychlorinated biphenyls (PCBs), are often non-toxic to aquatic insect larvae at concentrations commonly found in the environment. Such contaminants flux from aquatic ecosystems in large quantities in the bodies of emerging adult aquatic insects and expose terrestrial insectivores to toxic levels of pollution. On the other hand, contaminants that are less bioaccumulative, excreted during metamorphosis, and more toxic to insects, like trace metals, tend to affect terrestrial insectivores by reducing production of adult aquatic insects on which they prey. Management applications of this model illustrate type and severity of risk of aquatic contaminants to consumers of adult aquatic insects.