One of the perennial investments in Appalachia's infrastructure over the last two decades has been a funding and policy commitment to the reduction and closure of the socioeconomic gap created by the absence of broadband and internet access in Appalachian communities and schools. The Digital Divide looms as a topic of concern for policymakers, educators and citizens across the region, though steady progress has been chronicled. This paper offers a retrospective on the 20+ year commitment by regional stakeholders on digital literacy and equipping youth with internet access and skills. Using the deployment of internet connectivity to all K-12 schools in West Virginia as case study, this paper will document how this program successfully addressed policy, while igniting personal and community transformation. Moreover, the potential for how the program's success can be a model for areas in the region where technology gaps persist will be highlighted. A strategy for assessing the potential for virtual and tangible assets created through "Divide Closures" is presented. Finally, a framework for leveraging the foundational investment in Microsoft technology is discussed that could create inter and intra region connections that transcend geography, generations and career.