This chapter examines delays in primary education as a measure of educational inefficiency, focusing on gender disparities and intergenerational dynamics in a rural Philippine case. Based on household survey data from Bukidnon Province, the study finds that boys are more likely to experience greater delays in primary education compared to girls. Parental education plays a critical role, with higher maternal education reducing delays regardless of the child’s gender, while paternal education has a stronger impact specifically on boys. However, fathers generally have lower educational attainment than mothers, a disparity carried over to a similar gap between sons and daughters, perpetuating a vicious cycle. The analysis also highlights the effect of supply-side institutional changes, particularly an earlier school entrance age, on reducing delays. Female students benefit more significantly from this policy, showing greater progress toward minimal delays compared to their male counterparts. While household poverty exacerbates delays for both genders, cultural and contextual factors in rural Bukidnon further shape these patterns, where socioeconomic constraints and family dynamics interact in complex ways. The findings underscore the need for gender-sensitive educational policies to address the unique challenges faced by boys and girls, with attention to intergenerational and gendered dynamics in education.