The US Department of Veterans Affairs (VA) has adopted teledermatology, predominantly asynchronous, as an important strategy for improving access to expert skin care for its 9 million enrolled veteran patients. Despite the measurable success of its teledermatology program, one-fifth of all points of care have yet to implement teledermatology. The application of implementation science approaches offers the opportunity to systematically understand the VA’s teledermatology experience to yield insights into and lessons for implementing teledermatology widely as well as locally. Implementation frameworks and theories include the use of the Organizational Readiness for Change instrument as a prognosticator for implementation success, as well as the Reach, Effectiveness, Adoption, Implementation, and Maintenance (RE-AIM) framework to assess the longitudinal implementation of a teledermatology initiative for rural veterans. Development and implementation of novel technological innovations that introduce new teledermatology workflows into mature teledermatology environments were analyzed during the COVID-19 pandemic.