Cooperatively breeding animals occur in virtually every ecosystem on earth. Comparative and biogeographic studies suggest that that both benign and harsh, as well as stable and fluctuating, environments can favor the evolution of cooperative breeding behavior. The fact that cooperative societies occur in environments of such contrasting quality creates a paradox of environmental quality and sociality. The dual-benefits framework—which leads to the prediction that the ecological consequences of sociality (e.g. range size) vary depending on the benefits that individuals of each species receive by forming social groups—offers a potential resolution to this paradox. Here, we use a case study of two avian lineages, starlings (Sturnidae) and hornbills (Bucerotidae), in which environmental unpredictability appears to have opposite effects on the evolution of cooperation to test the dual-benefits framework. Consistent with previous work, harsh and unpredictable environments promote cooperative breeding behavior in starlings, which in turn leads to larger geographic ranges. However, cooperatively breeding hornbills occur in benign and stable environments, but sociality does not influence range size. Our study suggests that the paradox of environmental quality and sociality arises largely because cooperative breeding is an umbrella term, encompassing social species that form groups for different reasons. Differentiating between these reasons that social groups form is crucial for developing a predictive framework for understanding the evolution of cooperative breeding behavior.