Low-income students, many of whom reside in urban environments, often lack the support they need to prepare for postsecondary education, identify the best fit schools, apply for financial aid, enroll and persist in their studies, and, ultimately, graduate with a degree. Since 2014, a university school counseling department and a New York City high school collaborated to provide targeted and focused college readiness, awareness, and engagement activities to each and every student in the senior class through the direct involvement of school counseling preservice graduate students. The project's primary goals focused on student outcomes related to an improved graduation rate and postsecondary participation rate, with varying degrees of success. Participants in the high school-university partnership realized the value and importance of engaging students much earlier in career and college planning process.