Purpose To examine how qualitative narrative comments and quantitative ratings from end-of-rotation assessments change for a cohort of residents from entry to graduation, and explore associations between comments and ratings. Method The authors obtained end-of-rotation quantitative ratings and narrative comments for 1 cohort of internal medicine residents at the University of Illinois at Chicago College of Medicine from July 2013–June 2016. They inductively identified themes in comments, coded orientation (praising/critical) and relevance (specificity and actionability) of feedback, examined associations between codes and ratings, and evaluated changes in themes and ratings across years. Results Data comprised 1,869 assessments (828 comments) on 33 residents. Five themes aligned with ACGME competencies (interpersonal and communication skills, professionalism, medical knowledge, patient care, and systems-based practice), and 3 did not (personal attributes, summative judgment, and comparison to training level). Work ethic was the most frequent subtheme. Comments emphasized medical knowledge more in year 1 and focused more on autonomy, leadership, and teaching in later years. Most comments (714/828 [86%]) contained high praise, and 412/828 (50%) were very relevant. Average ratings correlated positively with orientation (β = 0.46, P < .001) and negatively with relevance (β = −0.09, P = .01). Ratings increased significantly with each training year (year 1, mean [standard deviation]: 5.31 [0.59]; year 2: 5.58 [0.47]; year 3: 5.86 [0.43]; P < .001). Conclusions Narrative comments address resident attributes beyond the ACGME competencies and change as residents progress. Lower quantitative ratings are associated with more specific and actionable feedback.