This study examines the outcomes of non-school internships hosted by two Appalachian Ohio organizations: Rural Action and Building Bridges to Careers (BB2C). As intermediary organizations, these entities work outside the boundaries of formal schooling to address issues of youth outmigration and sustainable community development through high school internships. This qualitative study, guided by the conceptual framework of community and career connected learning (CCCL), seeks to fill a gap in the literature where existing studies favor a distinctly urban-centric vantage point or focus on optimizing social mobility and developing skills needed to maintain a globalized, unrooted workforce. Previous program participants (2016-2020) between one to three years post-high school graduation (n = 25) were interviewed and data were analyzed using generalized issue focused analysis. Findings reveal impacts on participants': (a) perceived role within their rural communities, (b) career pathways, and (c) social capital acquisition. Participants indicated the internship positioned them to establish an initial career trajectory, while also leading them to reconsider their role within the community.