Latino/a undocumented students are among the population of students who are in danger of not graduating or pursuing college due to the unique set of challenges they face navigating education in the U.S. This study aims to understand undocumented students' experiences and the factors that impede them from furthering their education. As professionals in education, school counselors can offer a unique perspective on the barriers that college-bound undocumented students face when pursuing higher education. Using a phenomenological approach, data was gathered from counselors (N=14) across 10 school districts. The findings revealed undocumented students are faced with a myriad of challenges, socio-emotionally, academically, and career-wise, as they prepare to transition from high school to college.