Forest restoration has been undertaken on >200,000 ha of agricultural land in the Mississippi Alluvial Valley, USA, during the past few decades. Decisions on where and how to restore bottomland forests are complex and dependent upon landowner objectives, but for conservation of silvicolous (forest-dwelling) birds, ecologists have espoused restoration through planting a diverse mix of densely spaced seedlings that includes fast-growing species. Application of this planting strategy on agricultural tracts that are adjacent to extant forest or within landscapes that are predominately forested has been advocated to increase forest area and enhance forested landscapes, thereby benefiting area-sensitive, silvicolous birds. We measured support for these hypothesized benefits through assessments of densities of breeding birds and reproductive success of 9 species on 36 bottomland forest restoration sites. Densities of thamnic (shrub–scrub dwelling) and silvicolous birds, such as yellow-breasted chat (Icteria virens), indigo bunting (Passerina cyanea), and white-eyed vireo (Vireo griseus) were positively associated with 1) taller trees, 2) greater stem densities, and 3) a greater proportion of forest within the landscape, whereas densities of birds associated with grasslands, such as dickcissel (Spiza americana) and red-winged blackbird (Agelaius phoeniceus), were negatively associated with these variables. Vegetation structure, habitat edge, and temporal effects had greater influence on nest success than did landscape effects. Taller trees, increased density of woody stems, greater vegetation density, and more forest within the landscape were often associated with greater nest success. Nest success of grassland birds was positively related to distance from forest edge but, for thamnic birds, success was greater near edges. Moreover, nest success and estimated fecundity of thamnic species suggested their populations are self-sustaining on forest restoration sites, whereas these sites are likely population sinks for grassland and open-woodland species. We recommend restoration strategies that promote rapid development of dense forest stands within largely forested landscapes to recruit breeding populations of thamnic and silvicolous birds that have reproductive success sufficient to sustain their populations.