We document blockage of artificial Dryobates borealis (Red-cockaded Woodpecker) cavities by family Sphecidae (mud daubers) and large mixed-species aggregations of wintering Polistes (paper wasps) in cavity inserts at Great Dismal Swamp NWR in southeast Virginia. The large aggregations that we encountered are the only known cases of more than 2 paper wasp species cohabitating. Activity of Red-cockaded Woodpeckers within a cluster lessened the likelihood that paper wasps will aggregate in cavities, but not the likelihood that mud daubers will nest in cavities. The moist and saturated soils that predominate our field site may explain why these insects are more abundant compared to drier, upland habitats. Additionally, removal of hardwood trees may increase the breeding season habitat quality for paper wasps that hunt and nest in areas that are more open, while simultaneously limiting potential winter hibernacula habitat, typically found in mature hardwood tree cavities for Red-cockaded Woodpeckers. Common cavity management and translocation techniques may need to be altered to mitigate greater paper wasp and mud dauber activity at Red-cockaded Woodpecker cavity inserts in Pinus serotina (Pond Pine) pocosin habitat. We suggest using graduated rubber stoppers rather than screens that fail to exclude insect taxa or conducting translocations prior to the formation of winter aggregations of paper wasps.