National trends and goals have pushed beyond the dropout crisis and are now focused on raising the percentage of graduates prepared for college and career. This study examined a longitudinal cohort (n = 6443) of students in an urban, public school district in order to explore how districts and communities can redirect off-track high school students. The researchers explored timing to first-time college readiness in English and math using Event History Analysis. Variables under investigation included gender, first-generation college student status, college aspiration, enrollment in college preparatory courses, and participation in organized, extracurricular, college preparatory activities. Results indicated a student’s chances of being on the college-ready trajectory were highest in the 8th grade. Findings also revealed a positive association between higher parent education levels and college preparatory course enrollment, particularly in math.