A gap in achievement among Black men who pursue post-secondary education remains (Wood & Palmer, 2015). Many Black men start their college education at community colleges, but little is known about their experiences at Historically Black Community Colleges (HBCCs). The purpose of this dissertation of practice was to gain insights into the influence of College 101, also labeled Orientation to College 101 (ORI 101), on the transition of Black men to an HBCC. I utilized a qualitative case study design. The main data source were 15 semi-structured interviews, which were supplemented with closed-ended student survey responses on the ORI 101 course evaluation and the course syllabus. Using Schlossberg's transition theory as a framework, this study showed that ORI 101 provided support and fostered the development of strategies needed for success in college. Specifically, ORI 1010 increased essential college skills for Black men when delivered synchronously online and in-person; ORI 101 Helped Black men navigate campus; ORI 101 expanded Black men's support network. ORI 101, however, lacked culturally relevant information on HBCC status, information that could have been beneficial for students as they navigated the transition to the HBCC. This dissertation led to several implications for practice and future research. A personal reflection on the dissertation process and my learning from this process is also included. [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.]