The residency application process requires that applicants, their schools, and residency programs exchange and evaluate information to accomplish successful matching of applicants to postgraduate training positions. The different motivations of these stakeholders influence both the types of information provided by medical schools and the perceived value and completeness of information received by residency programs. National standards have arisen to shape the type and format of information reported by medical schools about their students, though criticisms about the candor and completeness of the information remain. Growth in the number of applicants without proportional expansion of training positions and continued increases in the number of applications submitted by each applicant contribute to increases in the absolute number of applications each year, as well as the difficulty of evaluating applicants. Few standardized measures exist to facilitate comparison of applicants, and the heterogeneous nature of provided information limits its utility. Residency programs have been accused of excluding qualified applicants through use of numerical screening methods, such as United States Medical Licensing Examination (USMLE) Step 1 scores. Applicant evaluation includes review of standardized measurements such as USMLE Step 1 scores and other surrogate markers of future success. Proposed potential improvements to the residency application process include limiting applications; increasing the amount and/or types of information provided by applicants and by residency programs; shifting to holistic review, with standardization of metrics for important attributes; and fundamental reanalysis of the residency application process. A solution remains elusive, but these approaches may merit further consideration.