Moving to a pass/fail curriculum has generally been associated with decreased levels of stress and increased medical student well-being. However, not much research has been done to identify the specific effect of retaining class rank in a pass/fail curriculum and how this might affect student stress levels. The purpose of the current study was to fill in current research gaps in this area and to provide further insight into some of the factors that contribute to medical student burnout. The study was carried out using the Medical Student Well-Being Index (MSWBI), a self-reported survey that evaluates medical student fatigue, depression, burnout, anxiety/stress, and mental/physical QOL on a weighted and unweighted basis. Additionally, a set of add-on questions developed by the research team were distributed to participants along with the MSWBI. These questions asked the students to determine whether the change to a pass/fail curriculum increased, decreased, or did not change their perceived stress levels and to identify the major sources of their perceived stress. Participants were full-time medical students enrolled at ETSU Quillen College of Medicine from the Fall 2019 to Spring 2020 terms. They were divided by graduation year and asked to complete the MSWBI and IRB-approved add-on questions once per school year during this period. The number of add-on question respondents from each class reporting an increased or unchanged level of stress since switching to a pass-fail system encompassed 62.6% of all respondents. The most common reason provided by respondents for either increased or unchanged levels of stress after switching to a pass/fail curriculum was the continued reporting of class rank. This work will be useful in determining the true sources of student stress within the medical education system. While a pass/fail curriculum may reduce medical students’ perceived stress, this data indicates that class rank remains burdensome for many. Understanding the underlying factors that influence poor medical student well-being can lead to better targeted interventions.