This article seeks to illuminate the social and educational context that leads undocumented college graduates to pursue graduate education in the face of the existing limited pathways towards employment and significant barriers toward graduate education. Although first generation immigrant Latinx students face adverse challenges as they pursue graduate education (Ramirez, 2011), this study highlights how immigration status complicates the pursuit of graduate degree attainment for undocumented college students. This paper draws on over two years of ethnographic data from a sample of twenty undocumented graduate students. The purpose of this study is to analyze the multifaceted nature of the decision-making process of undocumented college students to pursue graduate degrees, and how their commitment to matriculate in higher education programs is shaped by a myriad of social, familial, financial and institutional factors. This study illuminates the complex nature and context of undocumented students and their struggles to access higher education in California and across the nation.