Competition from hardwood species has long been considered a constraint on longleaf pine (Pinus palustris). However, evidence suggests that hardwood midstories may improve longleaf regeneration on xeric sites. Additionally, overstory retention for red-cockaded woodpecker (Leuconotopicus borealis; RCW) habitat may be inadvertently contributing to regeneration failures. Experimental plots in the North Carolina Sandhills were planted with containerized longleaf seedlings across a gradient of overstory density, and hardwoods were chemically controlled by treating at planting, treating after one year, or left untreated. Seedling survival (percent), growth (mass), and brown spot needle blight (percent infected seedlings; BSNB) were measured after two years. Seedling survival, growth, and BSNB infection rates were inversely related to overstory density. Midstory treatments did not significantly affect seedling survival, growth, or BSNB infection rates. Early results did not show facilitative effects from a hardwood midstory, but indicated overstory densities greater than 12 m2/ha negatively impact longleaf regeneration.