Red pine plantations may promote more desirable hardwood regeneration than hardwood stands because of differences in: 1) the composition and quantity of tree seeds available, and 2) abiotic and biotic properties of growth and establishment environments. However, information on how distance from hardwood edges, thinning of overstory pine, and site quality shapes hardwood regeneration properties in red pine plantations is scarce. Such information would aid in understanding and managing red pine plantation effects on hardwood regeneration processes and guide spatial and temporal rotations of such effects across landscapes. To elucidate relationships, we monitored hardwood seedlings and canopy openness across transitions from hardwood edges to red pine plantation interiors at 40 sites spanning a site quality gradient in northwestern-lower Michigan. Hardwood seedling density: 1) declined substantially from edges to interiors at all but low-quality sites before stabilizing 30-m into plantations, 2) was reduced, or not affected, by thinning despite positive effects on seedling light environments, and 3) was greater at intermediate than high- and low- quality sites. From edges to interiors, species composition shifted towards Acer rubrum, Quercus species, and Prunus serotina and away from Acer saccharum, Fagus grandifolia, Fraxinus americana, and Ostrya virginiana. Species increasing in relative abundance and/or density from edges to interiors were generally more drought-tolerant, shade-intolerant, large-seeded, and animal-dispersed than decreasing species. Shifts towards less shade-tolerant species from edges to interiors were consistent with increases in canopy openness and were most pronounced where changes in light were greatest (i.e., thinned plantations on high-quality sites). Changes in hardwood seedling density and composition were likely driven by differences across species in dispersal traits, seed characteristics, and relative adaptation to interior conditions (likely hotter, drier, and nutrient poor). To promote commercially valuable hardwoods, increase mast for wildlife, or improve climatic resiliency, the most suitable targets for conversion to hardwoods may be plantations with significant interiors (i.e., area > 30-m from hardwood edges) on higher quality sites adjacent to desirable seed sources (e.g., Quercus rubra, Prunus serotina, Acer saccharum). More desirable hardwood regeneration may result from reevaluating thinning timings and intensities originally designed to maximize red pine production. Our results also indicate that intentional management of surrounding hardwood forest composition (i.e., seed sources), within plantation retention of hardwood islands (e.g., mature oak stems), and greater control of Acer rubrum competition may further increase the desirability of hardwood regeneration in red pine plantations.