In this chapter, we synthesize the state of the science regarding ecological subsidies and contaminants at the land-water interface and suggest research and management approaches for linked freshwater-terrestrial ecosystems. Specifically, we focus on movements of animals with complex life histories and the detrital inputs associated with animal and plant matter delivered to freshwaters. We present a framework based on the physicochemical parameters of contaminants and how they shape the relationship between contaminant persistence within resource subsidies (“dark side” of subsidies) and movement of resource subsidies (“bright side” of subsidies) across ecosystem boundaries. This relationship between the “dark side” and “bright side” of subsidies defines an important parameter space that allows researchers and practitioners to predict the potential impacts of aquatic contaminants on resource subsidies and their interaction with other stressors on consumers. Ecological factors such as ecosystem productivity, community composition, and consumer prey preference shape the ecotoxicological outcomes of aquatic contamination on subsidies. Landscape factors such as lithology, hydrogeomorphology, hydroperiod, and land use underlie chemical, toxicological, and ecological patterns and provide the context within which effects of contaminants play out. Finally, effects of contaminants combine with effects of other global stressors on timing, quality, and quantity of subsidies that drive responses to contaminants at the land-water interface. Understanding the “dark side” of ecological subsidies requires expertise from multiple disciplines. We attempt to synthesize current knowledge from those disciplines and generate conceptual models that ecologists can use to guide future research in understanding cross-ecosystem subsidies and contaminant fate and effects.