Earning a college degree has been shown to have a number of positive socioeconomic impacts on individuals and society as a whole. Although researchers acknowledge that the decision to attend college is a complex process involving multiple factors, studies have focused primarily on individual reasons as part of a linear college choice paradigm. Individual obstacles to college attendance that consistently emerge in this strand of research include academic preparation, socioeconomic status, cost, family background, parental influence, motivation, and guidance counselor support (Harris & Halpin, 2002). College attendance rates are particularly low among students living in rural areas. Nationwide, only 59 percent of students from rural America choose to attend college, compared to 62 percent of their urban counterparts and 67 percent of students from suburban areas. (National Student Clearinghouse, 2015). The purpose of this study was to examine the college decision-making process of high school students in rural Vermont to better understand why fewer than 61 percent choose to attend college, despite more than 90 percent aspiring to do so at some point during their K-12 academic career (VSAC, 2016). A qualitative ethnographic case study approach was used to provide a unique student-focused perspective on the complexities of the college-decision making process as they go through it during their senior year of high school. A series of in-depth interviews were conducted with 10 students at two rural high schools throughout their senior year as they wrestled with an influx of information from multiple sources creating a series of pushes and pulls from guidance counselors, family members and friends with varying motives. Individual case study analyses were conducted on the following three groups of students based on their level of commitment to attend college at the start of their senior year: College Confident, College Considering and College Conflicted. A cross-case analysis of those three groups was also conducted. The result is a detailed account of how students in each group internalized and acted upon new information about their post-secondary plans, which depended heavily on when they received it, who they received it from and its quality. In most cases, the experience proved to be a frustrating, convoluted process that waxed and waned with each new piece of information. Ultimately, students made final college-going decisions based heavily on a combination of information that was not always accurate, sometimes misleading, and on the advice of at least one parent they perceived as having their best interest in mind.