Background Much has been written about Black undergraduate men's out-of-class engagement and social experiences, identity development, participation in intercollegiate athletics, and college enrollment and completion rates. Too little is known about their academic readiness and first-year college adjustment. Purpose The purpose of this study was to understand Black male students’ academic transition experiences in the first college year, with a particular emphasis on how they resolved academic challenges with which they were confronted. Setting This study was conducted at 42 colleges and universities in 20 states across the United States. Six institution types were included: private liberal arts colleges, public research universities, highly selective private research universities, public and private Historically Black Colleges and Universities, and comprehensive state universities. Participants The sample was comprised of 219 Black undergraduate men, mostly juniors and seniors, who maintained high cumulative grade point averages, were extraordinarily engaged in a range of student organizations, held multiple leadership roles on campus, cultivated meaningful relationships with faculty and administrators, participated in enriching educational experiences (e.g., study abroad programs), and earned numerous merit-based awards and honors for their college achievements. Research Design Qualitative research methods were used in this study. Specifically, phenomenology was used to understand what Black male students experienced in the first college year and how they experienced the transition phenomenon. Data Collection and Analysis Individual, face-to-face interviews were conducted with all 219 participants. Each interview was 2-3 hours. Moustakas’ (1994) process for phenomenological data analysis and Harper's (2007) trajectory analysis technique were used to analyze data collected for this study. Findings Two thematic categories of findings are presented in this article. First are reflections from students who experienced turbulence in their transitions from high school to higher education. Being underprepared for the academic rigors of college, the surprising mismatch between academic effort and first-year grades, the racial composition dissimilarities between their high schools and college campuses, and feelings of cultural misfit were factors to which participants attributed their initial adjustment challenges. The second category includes insights from achievers who transitioned seamlessly to college. They attributed their successful starts to strong academic preparation, prior experiences in demographically comparable educational environments, participation in summer bridge and college transition programs, and academically profitable relationships they cultivated in student organizations. Recommendations This article ends with several suggestions for helping Black undergraduate men adjust more seamlessly and resolve surprising academic transition issues encountered in the first college year.