In the 2012-13 school year, Kentucky led the nation with an 85.4 percent high school graduation rate for low-income students and a one-percentage-point graduation gap between low-income and non-low-income students. In 2013-14 the state ranked fourth in the nation with a seven-percentage-point incomebased graduation rate gap. Even though Kentucky's low-income graduation rate decreased slightly in 2014 to 84 percent and the gap grew largely because graduation rates for non-low-income students continued to rise, the state remains near the top in the nation for boosting graduation rates for low-income students, proving that this achievement is not an anomaly. In fact, Kentucky's progress reflects steady improvement since 2003 and shows that the state's efforts to raise graduation rates and increase educational attainment have paid off. This report examines how Kentucky made such gains in an era of higher standards and at a time when the number of low-income students has dramatically risen. This study is driven by three key questions: (1) What has Kentucky done to raise the high school graduation rate for all students and narrow the income-based achievement gap? (2) What are the historical roots over the last 25 years and recent contributions to this success? What leadership, legislation, policies, and practices have been the chief drivers of progress? (3) What lessons can be learned from Kentucky's continued progress and remaining challenges that can be shared within the state and beyond its borders? This research highlights four major themes that have driven much of Kentucky's progress over the last 25 years, and contributed to its narrow gap between low-income and non-low-income students. This report also takes a deep dive into three regions of Kentucky (Central Kentucky, Appalachia and Eastern Kentucky, and Northern Kentucky) to better understand what educators and communities are doing on the ground to improve educational opportunities for students. Appendices provide supplemental data tables. [Funding for this report was provided by the CE&S Foundation, James Graham Brown Foundation, Haile Foundation, United Way of Greater Cincinnati, and Strive Partnership.]