Objective: To determine barriers and opportunities to health insurance enrollment among an undergraduate students at a large urban university. Participants: Participants were 31 college students enrolled in 4-year and community colleges in the City University of New York (CUNY), and six health services and insurance enrollment specialists who facilitate and assist in the health insurance enrollment process for CUNY students. Methods: Focus groups were conducted with students and in-depth interviews with key informants in May 2017. Results: The research revealed important insights into how students perceive and value insurance and yielded recommendations for the university to improve enrollment of its students. Conclusions: Many colleges can increase student enrollment in health insurance by informing and educating students about the process. Improving enrollment processes can increase insurance rates and improve student population health.