There continues to be a severe under-representation of African Americans in the fields of information technology (IT) and computer science. The author contends that this is attributable, at least in part, to inappropriate assumptions about the nature of thinking, knowing, teaching and learning. He contends that attention given to these assumptions can improve learning environments, not only for African American students, but also for students of all ethnicities who experience difficulty in the existing school culture. This article is the case study of a project that selected 15 African American students experiencing some type of academic difficulty. These students were selected not only because of their academic challenges, but also because they exhibited an intrinsic interest in computer technology. The students were placed in two single-sex groups for instruction in Web development. While the ostensible objective was to introduce the students to the cognitive tasks involved in Web development, the underlying objective was to teach students who appeared unmotivated in the mainstream school context to engage cognitively in a relatively sophisticated domain. The learning environment used to do this was "socio-cultural" in nature, in that not only were the students exposed to the factual material and vocabulary needed for the domain (that is, from an objectivist perspective), and not only were the students allowed to work with this material in a way relevant to them as individuals (that is, from a constructivist perspective), but they were also allowed to help define the language of the classroom via peer learning and discussion. Such an environment was selected because of its potential to address the possibility of the learning environment being a "poor fit" for these students. Even though the contact hours were limited, it appeared that the girls quickly mastered the tasks and concepts required--and were able to articulate these concepts--while the boys mastered the tasks but did not appear to acquire the same mastery of the concepts as the girls. Much more work in this area is needed, but this case study indicates that the methodology used may not only facilitate a wider pool of African American students entering technology and science fields, but may also help students of various ethnicities that are struggling academically.