Due to the rigor and pace of undergraduate medical anatomy courses, it is not uncommon for students to struggle and fail initially. However, repetition of coursework places an additional burden on the student, instructor, and institution. The purpose of this study was to compare the exam preparation strategies of repeating and non-repeating students to identify areas where struggling students can be supported prior to course failure. As part of their integrated anatomy course, first-year medical students at Indiana University completed a metacognitive Practice-Based Learning and Improvement (PBLI) assignment prior to and after their first exam. In the PBLIs, students were asked to reflect on their exam preparation strategies, confidence, and satisfaction, as well as their predicted and actual exam performance. PBLI responses from non-repeating and repeating students were then analyzed quantitatively and qualitatively. A total of 1802 medical students were included in this study, including 1751 non-repeating and 51 repeating students. Based on their PBLI responses, non-repeating students were appropriately confident, somewhat satisfied, and more accurate when predicting their exam performance. Repeating students were overconfident, dissatisfied, and inaccurate when predicting their first exam performance on their initial, unsuccessful attempt but were more successful on their second, repeat attempt. Qualitative analysis revealed that repeating students aimed to improve their studying by modifying their existing study strategies and managing their time more effectively. In conjunction with other known risk factors, these insights into repeater and non-repeater exam preparation practices can help anatomy educators better identify and support potential struggling students.