The third year clerkship is an exciting yet challenging time for medical students (Cooke, Irby, & O'Brien, 2010). For the first time, students spend significant time in clinical settings (e.g., hospitals) assisting in the daily care of patients. Obtaining just-in-time and at point-of-care information and resources (Author, 2009) is one challenge faced by supervising doctors and students. Technology has been used extensively in point-of-care decision-making (Burke & Weill, 2012); mobile technology adds value to this activity. In this study, we explored how mobile tablets (e.g., iPads) were being used to support supervising doctors and medical students in three ways (1) supervising doctors learning the practice of academic teaching, (2) medical students learning the practice of Internal Medicine, and (3) supporting clinical decision-making for supervising. Results from a two-year study indicate that both faculty and students benefitted from and were challenged by the use of the iPads in clinical settings. Benefits included ready access to a teaching tool, access at point of care, and multiple resources to support decision-making. Challenges included keeping track of the tablet, network access, and speed of the network. Implications for improving practice and future research are suggested.