This study examined the experiences of first-generation college students who were enrolled in online degree programs at a traditional brick-and-mortar university located in the western United States. These students were viewed as "double first-generation" because they were not only the first in their family to pursue a bachelor's degree, but were also among the first generation in the history of American higher education to pursue public, postsecondary education in an entirely online format. The research was designed as a multiple methods case study that emphasized qualitative methods. Being exploratory in nature, the study focused on participant characteristics and the ways that they responded to and persisted in online degree programs. Data was collected through research that was conducted entirely online; it included an e-survey, two asynchronous focus groups, and individual interviews that were conducted via Skype. Grounded theory served as the primary method for data analysis, while quantitative descriptive statistics contextualized the case. The results of this study provide a window into the micro- and macro-level tensions at play in public, online postsecondary education. The findings indicate that these pioneering and traditionally underserved students drew from their diverse backgrounds to persist toward degree completion, overcoming challenges associated with time and finances, in hopes that their efforts would bring career and social mobility. As one of the first studies to critically examine the case of double first-generation college students, this study extends the literature in meaningful ways to provide valuable insights for policymakers, administrators, faculty, and staff who are involved with this population.