Most young people face challenges on the road to a college degree. They must make important decisions about career preparation, financing a college education, and how college and work fit together to ensure income security while in school. These challenges often seem particularly daunting for two groups of students: opportunity youth (OY)--the 5 million youth nationally aged 16-24 who are disconnected from both work and school--and first-generation college students. Many students from these groups come from schools or families that lack the resources to fully prepare them for college. This brief explores where policy can improve student pathways to a college degree. A goal of this research project is to advance the conversation on how colleges, community-based organizations, and the Commonwealth--most notably state education agencies--can systemize supports for OY and first-gen students. Four areas for improvement emerged: (1) align campus systems with student needs; (2) streamline academic progression; (3) build student navigation skills; and (4) connect the community and the campus. [Support for this project was provided by the Boston Opportunity Youth Collaborative (OYC).]