Background Medical schools face a growing challenge in providing a comprehensive educational experience. Students must graduate with not only the medical knowledge but also the requisite skills to care for patients and serve as physicians-in-training. Objective To assess whether residents felt prepared by their medical school training. Method We developed a questionnaire to assess resident attitudes towards various aspects of their medical school training and electronically distributed it among 107 United States training institutions. Results A total of 2287 residents responded. Overall, a majority (53.8%) agreed that 'medical school prepared me well to be a resident.' Most residents felt very well or mostly prepared in medical knowledge and clinical skills such as collecting a history (92.3 %), presenting a physical exam (86.1%), or pathophysiology (81.6%), but not for applied medical and psychosocial practices including endof-life care (41.7%), dealing with a patient death (46.3 %), and considering cost-effective care (28.7 %). Additionally, many residents reported feeling underprepared for time and fatigue management, debt, and medical-legal issues. Conclusions Medical school graduates generally feel well prepared for residency. However, they may be less prepared to face important psychosocial, cultural and professional issues. Ultimately, a greater emphasis on skills and psychosocial experience may yield graduates who feel better prepared for today's residency challenges.