Undergraduate medical educators seek to optimize student learning, improve grading transparency and fairness, and provide useful information to residency programs. Recently, the United States Medical Licensing Examination's shift to pass/fail scoring for Step 1 disrupted curricular and assessment operations, and schools' tiered grading practices have been scrutinized. In noting that significant institutional time and energy were being expended in addressing the current levels of student grade appeals, 6 public and private medical schools in the Northeastern United States engaged in an examination of grade appeals via a root cause analysis (RCA). From November 2021 to April 2022, the authors reviewed specific instances of grading challenges that the team of educators encountered previously. From May to June 2022, the authors met for a facilitated discussion of the question, "Why are students challenging grading processes and systems or outcomes?" From July to October 2022, the authors identified root causes by analyzing results from the fishbone diagram (process, equipment, materials, people, and environment) and using the "five whys" technique. Several potential explanations for grade appeals and challenging grading systems across institutions were identified, including variability in the quality or experience of evaluators, lack of clarity about the goals and expectations of clerkships and a lack of transparency about the grading process, having a tiered grading system, technical issues with equipment, and clinical productivity demands of faculty. In proposing solutions to root causes identified in the RCA, factors were mapped to Liaison Committee on Medical Education (LCME) standards to facilitate quality and process improvements in grading. Aiming to support the learning environment and a fair and equivalent assessment process, the authors present a novel RCA and LCME method that can contribute to improving grading systems and has the potential to enhance learning and success.