This document describes a study that used expert educator shifts to assess medical students on emergency medicine milestones. During the shifts, students were directly observed by attending physicians as they cared for patients, and were assessed on 10 milestones. Results showed that students who participated rated direct observation, feedback, and the educational experience more highly compared to previous students. The study concluded that expert educator shifts can effectively assess competency-based milestones and help prepare students for residency. Future directions involve developing an advanced clinical track to teach residency-level milestones prior to graduation.