Herbivory is rare among birds and is usually thought to have evolved predominately among large, flightless birds due to energetic constraints or an association with increased body mass. Nearly all members of the bird order Anseriformes, which includes ducks, geese, and swans, are flighted and many are predominately herbivorous. However, it is unknown whether herbivory represents a derived state for the order and how many times a predominately herbivorous diet may have evolved. Compiling data from over 200 published diet studies to create a continuous character for herbivory, models of trait evolution support at least five independent transitions toward a predominately herbivorous diet in Anseriformes. Although a nonphylogenetic correlation test recovers a significant positive correlation between herbivory and body mass, this correlation is not significant when accounting for phylogeny. These results indicate a lack of support for the hypothesis that a larger body mass confers an advantage in the digestion of low-quality diets but does not exclude the possibility that shifts to a more abundant food source have driven shifts toward herbivory in other bird lineages. The exceptional number of transitions toward a more herbivorous diet in Anseriformes and lack of correlation with body mass prompts a reinterpretation of the relatively infrequent origination of herbivory among flighted birds.