Recent data from Chicago Public Schools (CPS) show that active English Learners were less likely to graduate from high school (77% did so in 2023) than their peers (85%) and less likely to enroll in college (56% of 2022 English Learners high school graduates enrolled in college compared to 66 percent of their non-English Learners high school graduate peers), drawing attention to what supports these students need and what barriers they face on the road to college. To understand the academic performance in high school, college enrollment, and college persistence of English Learners, this study highlights metrics for former English Learners and different groups of active English Learners (at the time of enrollment in ninth grade). The focus of this study is on understanding different indicators of academic performance in high school, college enrollment, and college persistence of English Learners--including variation in attainment among active and former English Learners--to support their path to high school graduation and access to college. Using three cohorts of students who were first-time ninth-graders in the fall of 2014, 2015, and 2016 where 33% of students were English Learners, the authors conclude that English Learners are not perpetually struggling, as publicly reported numbers suggest, but specific groups of English Learners need more support. There are some commonalities among English Learners, but also some key differences, suggesting that there are different strategies that would be effective in supporting different English Learners groups. [This report was co-produced by the University of Chicago Crown Family School of Social Work, Policy, and Practice.]