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Students in the U.S. are underachieving in math and reading, which negatively affects transitions to postsecondary education (NAEP, 2015). Research shows that students exposure to college coursework in high school can increase academic outcomes for students and lead to successful transitions to college. However, many studies promote the use of early college programs that foster college readiness, without considering schools that may not be equipped to provide those opportunities for students. This article offers insight about the lack of college readiness for students, specifically students that attend urban schools, and the role that high schools play in combating these limitations. This article concludes with recommendations on ways to creatively immerse students from urban schools with college experiences.