Abstract Problem Reflective practice is necessary for self-regulated learning. Helping medical students develop these skills can be challenging since they are difficult to observe. One common solution is to assign students’ reflective self-assessments, which produce large quantities of narrative assessment data. Reflective self-assessments also provide feedback to faculty regarding students’ understanding of content, reflective abilities, and areas for course improvement. To maximize student learning and feedback to faculty, reflective self-assessments must be reviewed and analyzed, activities that are often difficult for faculty due to the time-intensive and cumbersome nature of processing large quantities of narrative assessment data. Approach The authors collected narrative assessment data (2,224 students’ reflective self-assessments) from 344 medical students’ reflective self-assessments. In academic years 2019–2020 and 2021–2022, students at the University of Cincinnati College of Medicine responded to 2 prompts (aspects that surprised students, areas for student improvement) after reviewing their standardized patient encounters. These free-text entries were analyzed using TopEx, an open-source natural language processing (NLP) tool, to identify common topics and themes, which faculty then reviewed. Outcomes TopEx expedited theme identification in students’ reflective self-assessments, unveiling 10 themes for prompt 1 such as question organization and history analysis, and 8 for prompt 2, including sensitive histories and exam efficiency. Using TopEx offered a user-friendly, time-saving analysis method without requiring complex NLP implementations. The authors discerned 4 education enhancement implications: aggregating themes for future student reflection, revising self-assessments for common improvement areas, adjusting curriculum to guide students better, and aiding faculty in providing targeted upcoming feedback. Next Steps The University of Cincinnati College of Medicine aims to refine and expand the utilization of TopEx for deeper narrative assessment analysis, while other institutions may model or extend this approach to uncover broader educational insights and drive curricular advancements.