This study examines the experiences of nine first-generation, single-mother college students, focusing on these intersecting, double-jeopardy identities. Participants' difficulty navigating college varied; contributing factors included family background, social capital, the type of college attended, and whether they established a mentor. The following themes were established: 1) realizing college is an option, 2) caught between two worlds, 3) college wasn't designed for us, 4) economic barriers, and 5) disparities in social capital. Our findings indicate colleges were unprepared to meet the unique challenges faced by this group. We present recommendations for the incorporation of specific supports in institutions and classrooms of higher education, including making implicit higher education customs explicit by creating cultural roadmaps to help students succeed, informing students of guidelines for successful communication with faculty, emphasizing and investing in completion of degrees as much as recruitment efforts, allowing parental accommodations in the classroom where possible, fostering avenues of personal connection and relationship-building with faculty and peers, and connecting students with financial and community resources as needed.