For the last several decades, a substantial amount of effort towards longleaf pine (Pinus palustris) restoration has taken place on public lands, while comparably less work has focused on private lands. Restoration has been hampered by various constraints associated with prescribed fire, such as legal liability, smoke management issues, and cost-related issues. The overall objective of this study was to examine factors influencing the application of prescribed fire for ecological restoration on private land. Key informant interviews were conducted to explore challenges and opportunities for restoration. Interviews examined informants’ interest in longleaf pine restoration, including reasons associated with not implementing prescribed fire, and motivations to apply fire. Findings demonstrate interest in ecological restoration, although this interest was tempered by challenges associated with complex land management practices. Such challenges included, prescribed fire costs, lack of knowledge, and concerns over regulatory issues. Still, informants expressed some interest in collaborative landscape management activities, whereby landowners would bundle expenditures and opportunities to conduct management activities Findings can be applied to policy and programs that increase prescribed fire in general as well as efforts to increase the range of native longleaf pine.