The Medical Student Performance Evaluation (MSPE) was introduced as a refinement of the prior “dean’s letter” to provide residency program directors with a standardized comprehensive assessment of a medical student’s performance throughout medical school. The author argues that, although the MSPE was created with good intentions, many have questioned its efficacy in predicting performance during residency. The author asserts that, despite decades of use and some acknowledged improvement, the MSPE remains a suboptimal tool for informing program directors’ decisions about which applicants to interview and rank. In the current approach to MSPEs, there may even be some inherent conflicts of interest that cannot be overcome. In January 2015, an MSPE Task Force was created to review the MSPE over three years and recommend changes to its next iteration. The author believes, however, that expanding this collaborative effort between undergraduate and graduate medical education and other stakeholders could optimize the MSPE’s standardization and transparency. The author offers six recommendations for achieving this goal: developing a truly standardized MSPE template; improving faculty accountability in student assessment; enhancing transparency in the MSPE; reconsidering the authorship responsibility of the MSPE; including assessment of compliance with administrative tasks and peer assessments in student evaluations; and embracing milestones for evaluation of medical student performance.