The purpose of this study was to retroactively explore how Latinx undocumented students currently enrolled at a single University of California (UC) campus navigated policies concerning accessibility and affordability as they worked toward their goal of pursuing bachelor’s degrees. Using a critical race theory (CRT) and Latino/a critical race theory (LatCrit) lens, this study examined how policies such as California Assembly Bill (AB) 540; the California Development, Relief, and Education for Alien Minors (Dream) Act; and Deferred Action for Childhood Arrivals (DACA) shaped participants’ college goals. Moreover, this study explored participants’ challenges accessing information that was relevant to their status needs and the forms of support these participants used to navigate this larger policy landscape. Guided by a critical policy analysis approach that interrogated and scrutinized racial politics driving policy, 19 Latinx undocumented student participants engaged in two semistructured interviews and completed an educational journey map, an introspective tool used to uncover details about significant people, places, and events shaping their journeys to the 4-year institution. The study also used document analyses to investigate the resources and forms of support available to the participants. These document analyses encompassed resources available at the individual university site, those within the larger UC education system, and those forms of support situated within participants’ local contexts. The study’s findings revealed how California AB 540, California Dream Act, and DACA were important in enabling participants to better afford their 4-year institution. Despite these positive effects, the findings uncovered challenges and tensions in accessing accurate information concerning these policies. Along these lines, the findings addressed how these policies are situated within the larger web of college affordability, thereby demonstrating how and where existing policy has failed to consider the full scope of undocumented students’ needs. Implications from this study provide practitioners and researchers with ideas that can support the academic trajectories of Latinx undocumented students in a manner consistent with the current policy landscape and emerging policy changes. Given the study’s policy-oriented focus, the findings also yielded recommendations for policymakers so the system-level challenges articulated in the findings can be better addressed.