We compared avian use of naturally occurring and planted woodlands in eastern South Dakota, USA, to evaluate whether planted woodlands support the same avian communities as natural woodlands. A stratified cluster sample was used to randomly select 307 public areas in which to survey planted (n = 425) and natural (n = 99) woodland patches. Eighty-five species of birds were detected in eastern South Dakota woodlands, 36 of which occurred in ??? 5 of 524 patches surveyed. The probability of occurrence for 8 of 13 woodland-obligate species was significantly greater in natural woodland habitats than in planted woodland habitats. Four of these species breed in relatively high numbers in eastern South Dakota. Only one woodland-obligate occurred less frequently in natural woodlands. Probability of occurrence for 6 edge and generalist species, including the brown-headed cowbird (Molothrus ater [Boddaert]), was significantly higher in planted woodlands. The avian community of planted woodlands was dominated by edge and generalist species. The homogeneous vegetation structure typical of planted woodlands does not appear to provide the habitat characteristics needed by woodland-obligate birds. We conclude that planted woodlands do not support significant numbers of woodland-obligate species and may negatively impact grassland-nesting birds by attracting edge and generalist bird species and predators into previously treeless habitats. Planted woodlands cannot be considered equal replacement habitats for natural woodland patches when managing for nongame woodland bird species. However, the preservation and maintenance of natural woodlands is critical for woodland-obligate species diversity in the northern Great Plains.