This qualitative study examines the lived experiences of both first-generation (FG) students and employees of an Upward Bound (UB) program. The purpose of this study is to explore how an UB program at a private university in the Midwest can aid in bridging the educational gap for FG students while faced with obstacles such as reaching, engaging, and creating an accessible academic environment for FG students. The data collection method used is semi-structured interviews providing personal experiences of both UB employees and UB alumni to identify themes and subthemes. This research demonstrated that FG students experience additional unique challenges due to their FG status and provides insight into critical areas that UB can target to remove obstacles that impact academic achievement. As a result of the study findings, two structured objectives were proposed in the action plan: (1) to create onboarding and continuous training for UB employees, and (2) community and relationship building. These objectives are provided as a foundation for UB to create a supportive and equitable environment that fosters academic success to ultimately aid in bridging the educational gap for FG students. [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.]