In the midwestern United States, oak (Quercus spp.) forests are considered critical habitat for conserving biodiversity and are a declining resource. Ecological conditions, such as deer herbivory and competition from more mesic broad-leaved deciduous species, have been linked to poor oak regeneration. In the Midwest, where up to 90% of forestland is privately owned, a greater understanding of social dimensions of oak regeneration success is especially critical to designing effective restoration strategies. We sought to determine factors that serve as direct and indirect constraints to oak restoration and identify policy mechanisms that could improve the likelihood for restoration success. We conducted in-depth qualitative interviews with 32 natural resource professionals working in the Midwest Driftless Area. We found that most professionals anticipate that oak will remain only a component of the future forest. Furthermore, they identified the general unwillingness of landowners to adopt oak restoration practices as a primary driving force of regional forest change. The professionals pointed to interdependent ecological and social factors, occurring at various scales (e.g., economic cost of management, deer herbivory, and exurban residential development) as influencing landowner oak restoration decisions. Professionals emphasized the importance of government cost-share programs and long-term personal relationships to securing landowner acceptance of oak restoration practices. However, given finite societal resources, ecologically- and socially-targeted approaches were viewed as potential ways to optimize regional success.