The issue of college readiness and student degree completion has become an issue in educational research over the past decade. The topic of college readiness is more than just academic; it involves a deeper understanding of student familial backgrounds, emotional preparedness, and other non-academic experiences, such as study skills and time management. Using Conley's 4 dimensions of college readiness as a conceptual framework, the current study aimed to understand the perspectives of 15 college-bound graduates from 2 study districts regarding how they felt about their higher educational preparation, the effects, if any, of their rural education, and how the adults around them influenced their college attendance. A case study design was employed to study these graduates. Graduates participated in focus groups, interviews, and filled out surveys on how college-ready they were upon high school graduation and how their secondary preparation affected their college-going plans, choices, and experiences. Typological data analysis was employed that included separating raw data into categories, then summarizing, analyzing, and coding data to identify themes within each typology. The findings revealed that graduates were satisfied with the education they received; however, many pointed to a lack of advanced coursework and poor college counseling as barriers to their perceived overall success in higher education. These findings will inform the efforts of secondary and post-secondary institutions in their work to improve student's postsecondary transition and degree completion. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]