Orthopaedic resident educators confront many important issues. This may be the most challenging time yet for orthopaedic education. A survey of program directors and chairs aimed to identify the major challenges in orthopaedic education. Many issues were identified, and the following four major themes emerged: (1) loss of professionalism, (2) too much emphasis on procedures, (3) lack of clinical experience, and (4) challenges with external oversight. Professionalism in taking care of patients may be compromised by work-hour limitations and affected by generational differences. Limitations to progressive, graduated responsibility include internal and external factors, resulting in a lack of opportunity. Overemphasis on case volume fosters a training environment where technical skill is seen as most important and can detract from teaching the basic principles of being a doctor, including shared decision making. This paper explores these major challenges to orthopaedic resident education in 2018. Substantial changes will be required to address these challenges, but better understanding of the issues they face should help educators identify, minimize, or ideally avoid threats to optimal resident education.