The necessity of a college degree is irrefutable. However, the path to college for undocumented students can be crowded with boulders, steep walls, or altogether non-existent. Drawing on interviews with 25 undocumented Latina/o students and 5 years (2012–2017) of school ethnography, I show that their college-going experiences are framed by the convergence of Hillcrest high school’s college practices and a broader shifting policy context—CA Dream Act 2011, DACA 2012, and CA Dream Loan 2014. I find that a pervasive silence regarding undocumented students’ distinct needs permeates Hillcrest’s college-going practices. This silence mediates the intended benefits of shifting policies by discounting the influence of students’ intersecting social locations (undocumented status, working-class position) as students strive to pursuit a post-secondary education. Undocumented Latina/o high school students’ experiences urge for a reconceptualization of college-going frameworks that account for morphing inequities within educational institutions in the 21st century.