This study examines the relationship between Cycle 1 of the Houston Independent School District (HISD) College Success Initiative and students' preparation for, enrollment in, and persistence in college. Rates of FAFSA submission, two-year applications, four-year applications, and on-time college enrollment all significantly increased during Cycle 1 of the College Success Initiative (2015-16 and 2016-17) when compared to the baseline year (2014-15). Student meetings with College Success Advisors (CSAs) were associated with a significant increase in the probability of a student submitting their FAFSA application and a significant increase in the number of two-year and four-year applications submitted. Additionally, these meetings were associated with a greater likelihood of students enrolling in college immediately following their high school graduation. There was also some evidence that aspects of the College Advising Initiative were most beneficial to historically disadvantaged race/ethnic groups and English learner (EL) students. These findings indicate that current efforts by HISD are improving the college enrollment rates of their students, and have the potential to close historic gaps in educational attainment.