Education administrators are placing greater demands on university faculty, staff, and admission counselors to enroll and retain more students. Understanding this transition and the associated challenges is important for institutions of higher education so they can better assist black male students as they navigate through college and universities.?However, research is extremely inadequate regarding the factors that contribute to enrollment and retention of Black male students. The purpose of this dissertation was to learn from men who identify as a Black male, attended a predominately White institution (PWI) and graduated with their 4-year degree what were the significant factors that contributed to their successful matriculation. This study was a phenomenological study (Creswell & Creswell, 2018) that used heuristic inquiry to investigate the experiences and perceptions of the research participants. Heuristic inquiry not only represents the exploration of the everyday human experiences of the participants but allows for the conscious or unconscious contributions of the researcher.?Ten Black males participated in this study. A 25-item questionnaire, developed by the author, was used to explore the college experiences of the participants. Using Nancy Schlossberg's Transition Theory (2008) as the conceptual framework for this study, the transition experiences during the Moving In, Moving Through, and Moving Out phases were explored. Information was captured and cataloged using the theoretical themes self, support, strategy, and situation. Data was collected via virtual interviews and coded using MAXQDA. Potential exogenous factors such as socioeconomic status, gender, and race?that affected scholastic success of the participants were also examined. The findings of this study revealed that the transition experiences of Black men during the onset of college enrollment and moving through their college experiences were largely negative. However, this study provided evidence that when Black male students, (1) Recognize their situation, that is the environment protective and risk factors (2) receive support, (3) are involved on campus with culturally relevant activities, and (4) understand and positively embrace their student identity as being black attending a predominantly White institution, there is a greater probability of success at PWIs. Prominent themes of covert and overt racism emerged from most research participants. Their stories of racism were slightly coded and cryptic regarding casual conversations with non-Black students, staff, and faculty. Study participants explained how the integration of one's Blackness and maleness into predominantly White spaces posed challenges to existing symbols of White standards and warranted a sense of wariness on behalf of Black students. The limitations, recommendations, and implications of this student are presented. [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.]