For first-generation students of color, the transition from high school to the community college can be a difficult one. This study explored how high schools and community colleges can work in partnership to improve the transition for first-gen students of color. A mixed-methods analysis aimed to first discern high school students' perceptions before their transition to college, while the secondary qualitative phase uncovered community college students' perceptions after their transition from high school to college. Findings describe portraits of students at four "loss points," that is, missed opportunities where many underrepresented students are lost to the system of higher education. An integration of quantitative and qualitative findings demonstrated that the first-gen underrepresented students do not have the same access to home- or school-based cultural capital with respect to crucial details and support to make the transition to college, even as compared to their first-gen White and Asian counterparts. Additionally, the high schools are promoting four-year institutions over community colleges, despite that the largest majority of first-gen students of color cannot access four-year colleges. Recommendations outline ways in which high schools and community colleges can best collaborate to shift this inequity by forming strategic partnerships, making data-driving decisions, engaging all students in the community college application process, and encouraging priority enrollment at community colleges for local students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]