In this chapter, the authors discuss how school counselors may create a college-going environment for African American males in middle school. The authors use Bronfenbrenner’s (1979) Ecological Systems Theory to explain how environmental influences impact African American males’ college trajectory, both positively and negatively. Moreover, they use Ecological Systems Theory to discuss how multiple stakeholders (e.g., school counselors and parents) and various structured activities that align with the Eight Components of College and Career Readiness (NOSCA, 2010) may promote college preparation among Black male middle school students. The authors also present two case vignettes as examples of how school counselors may assist African American males for postsecondary options. In closing, the chapter concludes with implications for educational policy, research, and practice.