The transition between medical school and residency is a complex, multifaceted process that is commonly a time of stress and uncertainty for medical students. Occupying most of a student's final year of medical school, the residency application includes a primary Electronic Residency Application Service application, a variable number of program-specific secondary applications, and interviews. The application process culminates with The Match. Orthopaedic surgery is among the more competitive specialties; thus, it is critical that all involved parties understand the complexity of the process and the numerous variables that play into such a critical decision point in the career trajectory of a future physician. It is important to provide a mentor with an overview of the residency application process, specifically with respect to orthopaedic surgery, so that they may be best prepared to guide their medical student mentee through the process and help them find success.