To improve patient access to skin care, the Department of Veterans Affairs (VA) developed a patient-facing asynchronous mobile teledermatology application (app), which allows patients to follow up remotely with dermatologists. To understand how the app would be received in VA, we examined Organizational Readiness for Change (ORC), an important prelude to effective implementation, which includes the shared resolve and collective ability of organizational members to implement a change. We used a mixed-methods multiple case study approach to assess ORC at three VA facilities. Data derived from a site process call, surveys, and semistructured telephone interviews of VA staff, field notes, and administrative data. Participants at all three facilities supported the intervention and recognized the value of using the app to increase patients' access to dermatologists, but expressed concerns largely related to disruption of the pre-existing clinical workflow. Participants at the facility most actively using the app had the highest overall ORC score and reported the most facilitators. Facility leadership support when guided by a clinical champion minimized barriers by recognizing the complexities of health care provision at specialty clinics. While provider buy-in remained a barrier, leadership, guided by the clinical champion, played a critical role instituting implementation strategies. The strong association between the ORC survey score and the presence of facilitators and barriers suggests that the ORC survey may be a rapid, convenient, and effective tool for health care systems to identify favorable sites for wider implementation of mobile telehealth care. Clinical Trials Identifier: NCT03241589.