Active-duty Air Force enlisted members face challenges associated with the transition into higher education. The problem addressed in this study was that 1 in 6 Air Force enlisted members find transitioning to higher education a challenging and stressful process. The purpose of this qualitative descriptive case study was to examine perceptions of active-duty Air Force enlisted members regarding their experiences with transitioning to higher education and take a deeper look into these challenges through a theoretical framework based on Schlossberg's transition theory. The data collection method was comprised and consolidated from in-depth semi-structured interviews that provided real-life views from participants with experience of this transition. The study included 10 participants currently serving as enlisted members in the United States Air Force. The data which were collected through the interviews were processed through thematic analysis with the use of NVivo software. The research questions derived categories and themes which were coded for further analysis. After the data were fully analyzed, it was found that higher education success was initially related to degree selection and members pursuing higher education through that of which they are personally passionate about. Themes also identified that the balance of family, school, and work as an active-duty enlisted member was the primary challenge associated with continuing education and was amplified by long, inconsistent, and unpredictable schedules to include deployments. Themes further identified the importance of degrees improving job performance and financial aid knowledge. Future enlisted members who are interested in pursuing higher education, as well as supervisors of these members could benefit from understanding the outcomes of this study to learn the lessons from the participants of this study. Additionally, higher education institutions could benefit from understanding needs to better support active-duty Air Force enlisted members. [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.]