One route to increase the number of baccalaureate degree holders in the US is for educators to guide students through the open door of the community college to the point of transfer to a four-year institution. This qualitative study is comprised of three companion projects aligned to examine the decision-making process of traditional-age students living in rural, southeastern Kentucky as they progress toward acquiring a bachelor's degree using the community college as a stepping-stone. Our team divided this project into three key transition points: (a) high school seniors' decisions to attend a community college as a means to acquire a bachelor's degree, (b) community college students' decisions that promote persistence to the transfer point, and (c) community college students' decisions in choosing a specific transfer university. Students' stories of sources of encouragement and comfort, and of barriers encountered and overcome, lead to a better understanding of the lens through which these students make sense of complex educational decisions. From this understanding, we developed a series of practical, informed recommendations to provide educational support tailored to the needs of students shaped by their Appalachian culture and other defining traits. Three common themes interweave through our three companion segments. Students' decisions are impacted by the value they place on (a) a sense of belonging associated with the comfort and familiarity of close personal relationships; (b) the emotional pull of region, family, and home which can limit perceived choices and opportunities; and (c) the acquisition of a college education as a means of obtaining a good job, often conflicting with the need to fulfill family obligations. This study provides greater focus on the middle step of this three-step process: persistence to transfer during the community college years. The findings identify a need for Tinto's (1975) integration theory to be revised to include insights offered by Bourdieu (1977) on the importance of mirroring habitus and building cultural capital that promote success within the immediate environment and within the broader, mainstream society. This study also calls for the development of practices that strengthen academic integration, building on Kegan's (1994) theory of cognitive development. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]