The purpose of this study was to explore the postsecondary education transition experiences of graduates of Choctaw Central High School (CCHS) who received support from the Tribal Scholarship Program (TSP) to better understand the barriers to successful postsecondary completion and the means to overcoming those barriers. Successful transitions are key for students to persist to academic completion. Studies show that American Indian students have low rates of college completion and experience a variety of factors attributed to withdrawal from college. This study provided insight into college success experienced by American Indian students and an understanding of the opportunities for a college education their scholarship program provides. Suggestions for improving the preparation of students and operation of the scholarship program are offered. The participants in this study were CCHS graduates who received support from the TSP for postsecondary education. A case study with a survey component research design was used in this study. Data from a cross-sectional survey, interviews, and observations were collected. A total of 87 past and present TSP supported students participated as survey respondents. Purposeful sampling in the form of maximum variation was used to select 6 respondents for researcher conducted interviews. The findings of this study documented four themes that characterized the transition experience of respondents to postsecondary education. Additionally, within these themes three general barriers to successful postsecondary completion were revealed. The general barriers included: (a) racial conflict with peers or faculty, (b) being overwhelmed academically, and (c) having to care for a legal dependent. The themes and barriers are discussed in the context of three primary factors related to postsecondary completion for American Indian students: sociocultural, academic, and personal factors. Recommendations included: (a) assessing and addressing the unique needs of nontraditional students in the Tribal Scholarship program, (b) arranging for an after hour study and tutoring facility for Tribal Scholarship Program students who commute from the reservation to college, (c) beginning orientation to the Tribal Scholarship Program with 9th graders, (d) providing on-campus mentoring opportunities for Tribal Scholarship Program participants, and (e) expanding this research to public school graduates who participate in the Tribal Scholarship Program.