The transition to college often occasions excitement as well as elevated stress for students. The latter may be especially the case for those with learning disabilities (LD), who can encounter problems both socially and academically. This study follows students both with and without LD during the first month of college to explore the relationships between LD status and two outcomes: loneliness/social distress and academic self-efficacy. In particular, we hypothesized that hope and optimism would mediate the relationship between LD status and these outcomes. The sample consisted of 344 first-year undergraduates at the beginning of the academic year (Time-1) and a month later (Time-2). Results showed that LD status predicted Time-2 levels of academic self-efficacy and loneliness only indirectly, demonstrating that relationships between LD and loneliness as well as between LD and academic self-efficacy are mediated by hope.