After receiving their medical degrees, medical residents gain intensive clinical experience in patient care during a series of practice rotations, which continue for approximately four years. Scheduling these clinical rotations is a complex process of assuring sufficient provider coverage for patients while constraining the weekly resident workloads to be within nationally published guidelines. Many constraints on the rotations have to be met, and when these are violated, as they often are in current practice, both patient safety and resident work-life issues suffer. Our main objective is to build a decision-support tool that would enable the chief residents and program directors to develop implementable schedules instantly and with higher-quality results. Using integer programming we developed an Annual Block schedule tool to assign residents to rotations and a Rotation Work schedule tool to assign residents to work shifts. We compare and confirm the superiority of our generated schedules over past manually built schedules using performance metrics identified through an expert review process. To further evaluate the impact of improved scheduling, we gathered resident perceptions through an online survey on how undesirable characteristics affect patient safety and resident work-life. We used the results to create a unified quantifiable measure of the total impact of the schedule and advance one step closer in developing and implementing a better rotation scheduling system.