The upcoming transition of the United States Medical Licensing Examination Step 1 to pass/fail score reporting has wide-ranging implications for the medical education community. The decision to discontinue 3-digit numeric score reporting comes following advocacy to change the exam because of its disproportionate importance in the residency match process, the negative impact the exam has on student well-being, and the prominent influence the exam has on medical school curricula. Shifting to pass/fail score reporting for Step 1 creates significant uncertainties to be addressed by the stakeholders in the transition from undergraduate medical education to graduate medical education. In this Invited Commentary, the authors reflect on the positive implications of this scoring change, potential negative ramifications that need to be proactively addressed, and future ways that the transition to residency can be optimized. The transition to pass/fail score reporting for Step 1 creates an opportunity to redefine the residency match process, to support applicant decision making, and to encourage a holistic review of applicants. These changes to the review process will require grace and trust among stakeholders, including students, as well as active support for students who might be negatively impacted during a complex implementation phase. By removing the dominance of Step 1 numeric scores from the residency selection process, the change to pass/fail scoring provides a unique opportunity for all stakeholders to work together and redefine the transition to residency while protecting students from unintended negative consequences.