This chapter analyzes the role played by technology in undergraduate medical education (UME) using two perspectives: how technology is used as a tool to facilitate teaching and how medical students are taught to use technology in the clinical setting. For each perspective, a survey of literature, published from 2009 to 2019, was conducted to understand the current state. Authors critically examine the current state and describe and analyze issues with it. Recommendations are made for improving the blending of medical education, technology, pedagogy, and clinical practice. The narrative in this chapter is at the intersection of digital technology, educational theories, and medical settings (educational and practice).