This study used a general two-level model to explore data from the National Education Longitudinal Study of 1988-1992 to determine the extent to which student-level (parental involvement) and school-level (school culture of college preparedness) factors individually and collectively influenced eighth grade students' eventual academic preparedness for college by the time they reached the twelfth grade. The study's models supported my foundational hypothesis that the middle school years play a critical role in preparing students for college. That said, the impacts of both parental involvement and school culture, at the middle school level, appear to have a very trivial influence, on average, on students' eventual levels of academic readiness for college. The study's models' random effects results, however, paint a slightly more complex picture. These resulted indicated that, at some schools within the study, some or all of the four parental involvement variables had a statistically significant impact on students' eventual ACRES scores. While I was unable to determine whether these significant effects were mostly positive or negative, it certainly supports the notion that parental involvement indeed plays an important role in preparing students to be academically prepared for college. Additionally, the study determined that students' middle school grades had the most positive influences on ACRES scores, and student poverty levels and first-generation status were associated with the most negative impacts on students' academic preparedness for college. The study concludes by calling on policymakers, educational leaders, teachers, and parents to focus their time, attention, and resources on the middle school years to improve students' eventual academic readiness for college.