Boys have a slight advantage in the number of live births in the US (about 101:100), so, all things being equal, it is reasonable to assume that they would populate institutions at about the same rate as girls. However, institutions are social structures, and in social systems all things are almost "never" equal, so, clearly, there are other forces operating to produce imbalances in high school graduation, college attendance and college completion. The remainder of this paper is devoted to the examination of these forces, some of which are well-documented in research, others supported in theory, and still others more speculative but still useful for creating or adjusting interventions to promote boys' college attendance and success. Like many issues in education, this one is tremendously complex and results from the interplay of social, economic, psychological, educational, and community factors. However, it is unrealistic to believe that any single institution, such as the school, can mount an effective intervention in all of these areas and still do their core job of teaching content and skills to their students. Although this essay explores each of those contributory factors in some detail, the final recommendations for successful interventions assumes (1) that the program is school and community based, (2) a comprehensive program will address multiple factors, and (3) such programs may not be focused on boys exclusively (in accordance with most district policies and both state and federal law), but will be integrated into more comprehensive programs to promote college achievement. Also, for the purposes of this paper, much of the information addresses characteristics and conditions of boys who are the most unlikely to attend college (e.g., poor, minority, urban or rural) rather than those who are likely to be college-bound regardless of special interventions. (Contains 1 footnote.) [This paper was prepared for Oregon GEAR UP and the Ford Family Foundation.]