As many as a quarter of undergraduate college students are placed on academic probation at least once during their college career. In addition, first-generation college students are even more at-risk for stopping out or dropping out due to being less academically prepared than their non-first-generation peers. In order to examine factors that influence first generation student academic risk and success, this exploratory study examined the intersection of academic standing and four primary conceptual contributors: academic integration, personal adjustment, family and social adjustment, and psychological factors. Survey data were collected from first generation undergraduate students at an urban research university who were placed on academic probation and those who returned to good standing. Six overarching themes emerged that demonstrate critical importance in first generation student academic success: 1) overall study skills, 2) class attendance 3) health-related issues, 4) financial difficulties, 5) family and personal issues, and 6) physiological symptoms. In addition, these factors appear to have additive and multiplier affects for students. First generation students may be able to overcome one set of factors but each new dimension can further inhibit academic good standing. Recommendations include mandatory advising and college success classes.