Background: Rotation evaluations reflect the resident-perceived value of clinical experiences in graduate medical education. In this study, we sought to improve the quality of education for internal medicine residents during their inpatient medicine rotation. Methods: Program stakeholders critically appraised a core medicine rotation at a university-affiliated U.S. Veterans Affairs Medical Center utilizing end-of-rotation evaluations by residents. Thematic analysis identified three areas for improvement: culture, communication, and workload. Solutions were developed to address each theme: (1) site-specific orientation was provided to new trainees, (2) real-time notification of admissions occurred via secure messaging platform, and (3) an assistive rounding tool was integrated into the electronic medical record. Outcome measures of education were obtained via end-of-rotation evaluations by residents. Results: This study included 198 pre-intervention and 58 post-intervention evaluations by trainees from October 2022 through December 2023. Using a 5-point Likert scale, the quality of education improved from good to very good (3.26 to 4.02, +15%, p < 0.001) over the course of one year. All four subcategories also improved: diversity/quality of pathology (0.33; +7%), supervision (0.50; +10%), workload (0.42; +8%), and learning value (0.51; +10%). When the five categories are compared immediately pre-intervention (fourth quarter of 2022-2023 academic year) to full post-intervention (second quarter of 2023-2024 academic year) using a paired t-test, the change was statistically significant (p = 0.007). Conclusions: Significant educational enhancements were achieved over time for a core rotation in a residency program using solutions developed from interconnected themes found in learner evaluations.