First Generation (FG) students' pursuit of higher education continues to be initiated at community colleges at high rates; these two-year Higher Education Institutions (HEIs) are critical in bridging the gap for an increase in degree completion at four-year HEIs. The purpose of this study is to explore the institutional barriers, indicators, and participant experiences faced by FG students in preparation of the vertical transfer process from a two-year HEI to a four-year HEI. As literature suggests, there is still a lack of development and implementation of key indicators for an FG student's readiness including institutional transfer processes that may inhibit an efficient transfer to benefit the aforementioned population. This comparative case study analysis of the transfer processes, in preparation of FG students' transfer from a two-year to a four-year HEI, is imperative for professionals in higher education to utilize when developing interventions, but also in assessing adequate student support resources for vertical transfer, development of viable institutional articulation agreements and indicators for preparation and readiness. The analysis of the study found similar answers to previous research findings regarding preparation as it is crucial for the effectiveness of the transfer process and as a main indicator for FG students' successful vertical transfer from a two to a four-year HEI. The finding, preparation, as an indicator of vertical transfer for FG students, enhances the transfer process in higher education, whereby accelerating the rate of college 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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]