The general problem addressed by this study was that students who have been retained in the elementary grades were more likely to drop out of high school than their low achieving but socially promoted peers. The specific problem addressed in this study was that it is unclear what factors during students' retained years contribute to their inability to complete high school or post-secondary education in rural and urban settings. The purpose of this qualitative case study was to learn adult students' perceptions of being retained in early grades in rural and urban school settings. The theory that guided this study was critical theory. The students in a rural and urban Adult Education Program, an online Adult Facebook Group called GED Math Test Tutor and the students in College-Adult Literacy Services, were recruited to participate in the study. The criteria to participate in this study were those students who were retained in the elementary grade (K-6) and who did not complete high school (9-12). The researcher created the individual and focus group interview protocol. Interview and focus data were analyzed through Quirkos, using content analysis. From RQ1 six themes emerged to include: a need for additional help, resources and support prior to being retained; feeling left behind, embarrassed, inadequate, weird and scared; academics and school were viewed negatively, differently, hard and indifferent; male minority students were likely to be retained; educated in both rural and urban settings; and fifty percent of the participants believed that children should be retained, and fifty percent of the participants believed that children should not be retained. From RQ2 three themes emerged. These themes emerged to include multiple challenges, life issues, lack of motivation and no parental support; inability to make good money and have a career; and overall, their academic career turned out positive. [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.]