Results of a field study of the influences on Black male undergraduate students' participation in IT fields at a Predominately White Institution and Historically Black College and University are presented. This analysis shows how inadequacies within the academic pipeline present themselves as barriers to success for Black students. The findings are evidence that despite barriers Black students are not giving up on the Information Technology discipline despite the low number of Black professors at PWIs and HBCUs. The digital divide is once again shifting from usage to empowerment. Stereotype threat is threatening Black identity as Black males try to adapt to a field in which they are vastly underrepresented. A logical next step for researchers is to identify ways in which Black students are being affected by these inequalities. These findings indicate that Black students are disadvantaged in IT fields and steps must be taken to ensure they do not remain victims of a leaky academic pipeline.