Telehealth visits have become an integral model of healthcare delivery since the COVID-19 pandemic. This rapid expansion of telehealthcare delivery has forced faculty development and trainee education in telehealth to occur simultaneously. In response, academic medical institutions have quickly implemented clinical training to teach digital health skills to providers across the medical education continuum. Yet, learners of all levels must still receive continual assessment and feedback on their skills to align with the telehealth competencies and milestones set forth by the Association of American Medical Colleges (AAMC) and the Accreditation Council for Graduate Medical Education (ACGME). This paper discusses key educational needs and emerging areas for faculty development in telehealth teaching and assessment of telehealth competencies. It proposes strategies for the successful integration of the AAMC telehealth competencies and ACGME milestones into medical education, including skills in communication, data gathering, and patient safety with appropriate telehealth use. Direct observation tools in the paper offer educators novel instruments to assess telehealth competencies in medical students, residents, and peer faculty. The integration of AAMC and ACGME telehealth competencies and the new assessment tools in this paper provide a unique perspective to advance clinical practice and teaching skills in telehealthcare delivery.