Background There is emerging evidence that learners may be suboptimally prepared for the expectations of residency. In order to address these concerns, many medical schools are implementing residency preparation courses (RPCs). Objective We aimed to determine trainees' perceptions of their transition to residency and whether they felt that they benefited from participation in an RPC. Methods All residents and fellows at the University of Michigan (n = 1292) received an electronic survey in July 2018 that queried respondents on demographics, whether medical school had prepared them for intern year, and whether they had participated in an RPC. Results The response rate was 44% (563 of 1292) with even distribution across gender and postgraduate years (PGYs). Most (78%, 439 of 563) felt that medical school prepared them well for intern year. There were no differences in reported preparedness for intern year across PGY, age, gender, or specialty. Overall, 28% (156 of 563) of respondents participated in an RPC and endorsed feeling prepared for intern year, which was more than RPC non-participants (85% [133 of 156] vs 70% [306 of 439], P = .029). Participation in longer RPCs was also associated with higher perceived preparedness for residency. Conclusions This study found that residents from multiple specialties reported greater preparedness for residency if they participated in a medical school fourth-year RPC, with greater perceptions of preparedness for longer duration RPCs, which may help to bridge the medical school to residency gap.