The purpose of this study was to examine the perceived academic obstacles of first-generation students in comparison to non-first-generation students. Using the Student Experience in the Research University (SERU) completed by approximately 58,000 students from six research universities, the researchers used nonparametric bootstrapping to analyze differences between first-generation and non-first-generation students' obstacles to academic success. The results suggest that first-generation students more frequently encounter obstacles that compromise their academic success as compared to non-first-generation students, such as job responsibilities, family responsibilities, perceived weak English and math skills, inadequate study skills, and feelings of depression. Implications for learning assistance professionals are outlined. (Contains 1 table.)