This paper focuses on findings based on analysis of perceptions of teachers and parents on how schoolboys in Kirinyaga and Nairobi counties constructed masculinities as they negotiated manhood in the midst of a clearly defined race towards attaining Education for All (EFA) goals in Kenya, by end of 2015, which is around the corner –metaphorically speaking. The paper is based on a FAWE1-sponsored study conducted in 2012 and 2013 titled “Girl-specific education focus and boys’ participation, performance and construction of masculinities in selected Kenyan schools”. The study posted major school-based findings that were shared through the CICE Research Paper Series No.5 whereby, boys emerged as relatively underperforming in the schooling project compared with their female peers. It was, however, not feasible to include findings of the interplay of parents (fathers and mothers) and teachers and the role and interpretations of constructions of masculinities in their respective school communities. This paper therefore undertakes to fill up this void by foregrounding findings in this regard, specifically the shaping of masculinities among schoolboys as men-in-the-making navigating the pathways to manhood. Conducted in an African Kenyan context, this study raises interest in the multifarious interpretations of the basic feminist standpoint theories that present men as a group that is socialised from childhood to benefit from structures of power – social, economic, political, or otherwise- that are designed to oppress women and girls as a gender category. The study design departed from the traditional Kenyan gender research that often foregrounds girls’ education independent of that of boys, and which consequently fails to problematise boys’ schooling and their construction of masculinities in a comparative manner. For many parents (mothers and fathers) and teachers, schooling in itself did not appear to offer realistic masculine modelling for boys compared with the girls and as such, the boys were disillusioned and distracted from schooling as they searched elsewhere for models of successful masculinities to emulate.