Students with disabilities are attending postsecondary school in increasing numbers. College students with disabilities have lower retention rates, take longer to complete degrees, and have lower degree completion rates than do their peers without disabilities. Thus, students with disabilities face a number of significant challenges adjusting to postsecondary school and have unique transition needs. In addition to serving a greater number of students with disabilities, many colleges and universities are also experiencing an influx of "first-generation" college students. Many first-generation students are less academically prepared than are continuing-generation students when entering postsecondary educational environments. Once admitted, first-generation college students have lower college persistence and attainment rates than do their continuing-generation peers, and these effects hold even after controlling for socioeconomic status (SES), institution type, and attendance status. Moreover, first-generation college students often face unique familial, cultural, and social transitions that may make the transition to, and completion of, postsecondary school challenging. The current investigation was undertaken in light of growing evidence that disability status and first-generation status are factors that place a student at risk of experiencing difficulties adapting to and completing postsecondary school. Although both of these student characteristics are indicative of risk in isolation, the authors were interested in developing further understanding about the dual challenge, or cumulative risk, associated with having a disability and being a first-generation college student. (Contains 3 tables and 1 figure.)