Rural community college students face unique difficulties in higher education for many reasons, including the resources they typically have access to, their collective histories, and in many cases, the preparation they received in high school. These challenges might be low-performing secondary schools, a lack of tradition and precedence in attending college, and even limited technology connectivity. These difficulties can be seen as barriers to college attendance, and it is important to understand how rural community college students see these barriers, and even more important to understand how they can be overcome. The current study sought to take the first step in understanding what inhibits college student enrollment by exploring self-reported barriers to community college matriculation. Using two case study institutions and a modified survey instrument, results largely supported existing research in that preparation for postsecondary education and finances were critical in deciding whether or not to enroll in the community college. Additionally, parental enrollment in higher education was perceived to play a role in attending college, validating the growing literature base on college attendance, in general, and rural students in particular. Somewhat contradictory to the literature of rural education, however, was the finding that technology connectivity was not seen as a barrier to education.