As part of the Accreditation Council for Graduate Medical Education's Next Accreditation System, residency programs must connect resident-physician education to improved patient care outcomes. Residency training programs, however, face multiple obstacles in doing so. Results from residency quality improvement (QI) curricula tend to show improvement in simple process-based measures but not in more complex outcomes of care such as diabetes or blood pressure control. In this article, the authors describe the evolution of their QI educational program for internal medicine residents at the University of Cincinnati Medical Center within the structure of a novel training model called the Ambulatory Long Block. They discuss a resident-run project that led to reduced rates of patients with uncontrolled diabetes as an example of improvement in outcome measures. Despite favorable results from that particular resident group, the successful intervention did not spread practice-wide. Using this example, they detail the phases of evolution and lessons learned from their curriculum from 2006 to 2014 within a framework of previously published general principles for successful QI education, including those of exemplary care and learning sites. Successful programs require leadership, faculty expertise and mentorship, data management, learner buy-in, and patient engagement. Their experience will hopefully be of help to others as they attempt to simultaneously improve care and education. Further research and innovation are needed in this area, including optimizing strategies for strengthening resident-driven projects through partnership with nursing, allied health, and longitudinally engaged faculty members.