Digital health is an umbrella term for components of health care using computer platforms, software, connectivity, and sensors to augment the recording, documentation, and communication of clinical information. The functions of digital health may be viewed in three domains: (1) the repository for patient information, (2) monitoring devices, and (3) communication tools. Monitoring devices have provided robust information as diagnostic and prognostic tools in office and hospital settings. In this review, as a case study, we will discuss the research and our direct clinical experience of electronic medication monitoring technology and the potential benefits to patient care, and the opportunities and perils encountered in using this approach for patients with moderate to severe asthma, including issues related to patient uptake and concerns for bias, impacts on the provider-patient relationship, and discussions regarding monitoring of rescue medication use in exacerbations. Additionally, although there is evidence for improvements in various aspects of patient care afforded by electronic medication monitoring, these devices have not yet seen widespread uptake in clinical settings, and we will discuss the steps needed to address these barriers and keep these important devices available for patient use in the future.