Academically underprepared learners have been enrolling in college at increasing rates over the last several decades, yet their success rates in the courses designed to remediate their deficits have remained low. Theses courses serve as either gateways or gatekeepers to certificates and degrees for academically underprepared college students seeking to increase their opportunities for economic stability. The high attrition rates in college remedial studies suggest that they are serving as gatekeepers more often than gateways, interfering with students' educational attainment plans. This qualitative case study addressed the question: How do academically underprepared college students at a two-year minority-serving institution experience the transition into, through, and out of pre-curriculum studies to earn full enrollment in curriculum courses? Framed by transition theory, this study found that the participants: 1) experienced enrollment in pre-curriculum courses as stigmatizing, marginalizing, and as a threat to identity; 2) needed time to adapt their assumptions and behaviors and develop the internal and external resources they needed to support their progress through pre-curriculum courses; and 3) that the participants who internalized these adaptations developed interpersonally, intrapersonally, and cognitively. This study also found that the participants' interactions with empathetic faculty were critical to their willingness to adapt their assumptions and behaviors and develop the resources they needed to complete their remedial studies. [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.]