Because safe transitions of care are critical to patient safety, it is important to prepare physician trainees to assist in patient transitions from the hospital. As part of a discharge skills workshop for medical students, a brief reflective exercise was used to understand student perceptions of discharge problems and encourage application of classroom learning. Written reflections completed before and after the workshop were analyzed qualitatively to identify barriers to discharge observed on clinical clerkships and evaluate how the discharge skills workshop influenced student understanding of safe discharges. Students also completed a quantitative evaluation of the workshop. Seventy-eight of the 96 students (81%) at the Johns Hopkins University School of Medicine who participated in the discharge skills workshop volunteered to submit their written reflections. Eighteen themes were identified within two domains (barriers to safe discharges and solutions to improve discharges). The most commonly cited barrier was the sense that the discharge was rushed or premature. Three of the barrier themes and six of the solution themes were related to the importance of communication and collaboration in safe discharges. Students reported that the reflective exercise personalized the learning experience (mean 3.27 ± 0.86 on a scale of 1 (not at all) to 4 (a lot)). Students observed barriers to safe discharges on their clerkships related to poor communication, insufficient time spent planning discharges, and lack of patient education. Brief reflection encouraged students to apply lessons learned in a didactic session to consider solutions for providing safer patient care.