The Cooperative Extension System is at a crossroads regarding educational program delivery and clientele relationships in a digital age. To "help prepare counties for a future that demands increased use of technology for improving work efficiencies and expanding audience outreach," an assessment team was appointed to conduct a case study to investigate the potential for adoption of technology in county Extension programs in the Oregon State University Extension Service. This article contains key findings and recommendations in response to questions the team was charged to answer and assumptions it was asked to explore, many of which have national relevance.