The development of core entrustable professional activities (EPA) for entering residency and Accreditation Council for Graduate Medical Education's milestones have spurred thinking about the fourth year of medical school as a transition to residency. In this monograph, we lay out our specialty focused post-clerkship curriculum and report learner and residency director perceptions over the first three years of implementation. Ongoing curricular monitoring has reinforced core principles but has also informed actionable quality improvement efforts. EPA-focused learning experiences, integration of specialty-specific milestones, addition of the feedforward process, and accessible mentorships have been key curricular elements to guide the transition to residency.