Recent advances in our knowledge of parasitic and mutualistic associations have confirmed the central role of coevolutionary interactions in population and community ecology. Here, we discuss the potential coevolutionary interdependence of the strength and specificity of symbiotic interactions with the complexity and productivity of their environment. We predict that interactions become less beneficial with increasing environmental quality and that the association of productivity with symbiont specificity depends on the relative strengths of tradeoffs between host range and other life-history parameters. However, as biotic complexity increases, pathogen specificity is predicted to decline, whereas mutualist specificity will increase. Testing these predictions on a geographical scale would contribute significantly to the predictive science of coevolution, and to our ability to manage biological interactions embedded in increasingly fragmented landscapes.