Understanding how habitat amount and configuration affect species richness, occurrence or abundance has been one of the major foci of research in ecology and biogeography, given its central importance for conservation planning and landscape management. We conducted bird point counts within clearcuts and mature pine stands of different sizes and configuration in working pine forest in north-central Mississippi to determine species associations. Early-successional and mature pine focal species showed varying response to the proportion and proximity of vegetation conditions in the landscape. While elements of configuration exhibited a greater influence on predicted avian abundance in this landscape, meaning many species require a mosaic of habitat conditions that come from both early-successional and mature vegetation types. Efforts to combine management of timber and conservation of songbirds must consider both species’ habitat requirements and the distribution of these requirements in the landscape.