Technology failures in telehealth are common, and clinicians need the skills to diagnose and manage them at the point of care. However, there are issues beyond technology failures mediating the effective use of telehealth. We must teach best-practice procedures for conducting telemedicine visits and include in instructional simulations commonly encountered failure modes so students can build their skills. To this end, we recruited medical students to conduct a Healthcare Failure Modes and Effects Analysis (HFMEA) to predict failures in telemedicine, their potential causes, and the consequences to develop and teach prevention strategies. Sixteen students observed telehealth appointments independently. Based on their observations, we identified four categories of failures in telemedicine: technical issues, patient safety, communication, and social and structural determinants. We proposed a normalized workflow that included management and prevention strategies. Our findings can inform the creation of new curricula.