Introduction: Digital health software technologies (DHSTs) have the potential to shift models of care delivery and improve patient outcomes. Health-care students lack training to prepare them for the growing breadth and depth of DHSTs that they will need to identify, assess, and use in their future clinical careers. The implementation of this pilot digital health curriculum aimed to provide health-care trainees skills to identify, assess, and use DHSTs in their future clinical careers. Materials and Methods: From June to August of 2021, the authors implemented a 10 weeks pilot educational internship in partnership with the Accelerated Digital Clinical Ecosystem (ADviCE), a multi-institutional collaborative created by physicians within University of California, San Francisco Health Informatics. Interns completed a customized digital health didactic program developed by program faculty, including a speaker series with clinical informaticists in the field, journal club discussions, and intern-led presentations. In addition, interns were given real-world educational opportunities to directly interact with DHST vendors in the process of creating a DHST registry. Interns also completed a postcourse survey to procure feedback about the pilot program’s strengths and weaknesses. Results: Interns learned from a didactic educational curriculum that included more than 10 h of live lectures, 3 supplemental readings, and structured interactions with 74 DHST vendors. Based on a survey to assess interns’ satisfaction with the internship, interns ranked the expert speaker series the highest with an average standard deviation ranking on a 5-point Likert scale of 4.6 (0.57) and journal club discussions the lowest with a ranking of 4.31 (0.96). Interns also gave feedback on recommending the internship to future students with a ranking of 4.6 (0.65). Conclusion: This first internship led to the positively favored and successful execution of a remote educational experience exploring digital health in medicine, while also giving interns direct interaction with a broad array of digital health companies.