Although the number of dental professionals has seen a modest rise since 2011, nearly all counties in North Carolina—98 out of 100—are classified as Dental Health Professional Shortage Areas by the Health Resources and Services Administration, highlighting a persistent gap in access to both primary and specialized oral healthcare. Providers in these underserved regions often face challenges when attempting to refer patients to oral and maxillofacial pathologists. The COVID-19 pandemic in 2020 further accelerated the adoption of digital solutions, as social distancing measures and lockdowns forced dental schools and practitioners to explore alternative approaches for consultations, teaching, and patient care. This study shares our institution’s experience using teledentistry to deliver specialized oral healthcare in rural settings. We conducted a seven-year retrospective case series analyzing patients who underwent remote evaluation of oral lesions, either synchronously or asynchronously, at ECU School of Dental Medicine and an affiliated satellite clinic. For cases that required surgical sampling, we compared the initial clinical impressions and differential diagnoses with the final pathology results to evaluate the diagnostic reliability of teledentistry assessments. A total of 71 patients were included. The majority of consultations were performed asynchronously. Most cases were referred due to suspected malignancies or infectious/reactive lesions, which accounted for 42% and 25.3% of consultations, respectively. These findings indicate that teledentistry can play a crucial role in extending specialized oral healthcare to rural communities by reducing patient travel, shortening the time to diagnosis, and minimizing the number of visits required. Teledentistry offers clinicians a practical and effective tool for evaluating and diagnosing oral mucosal lesions in remote and underserved populations.