This article examines the emerging unfair inequality in Kenyan secondary schools through comparative case studies of three secondary schools in western Kenya. Qualitative data were collected through fieldwork over a four-year period, with participant observation and semi- or non-structured interviews, to understand how interactions among schools, households, and communities impact the improvement of educational quality. This study demonstrates that educational inequality stems from economic background and academic performance. While establishing new schools allowed students to choose better schools in their vicinity, increasing school competition resulted in a school hierarchy restricting uniform access due to factors of affordability and academic achievement. This suggests that the unplanned establishment of new schools constrains vulnerable students from continuing their education. Expanding educational opportunities and improving quality are important facets of education; however, it is necessary to pay attention to the beneficiaries of this process, as economic inequality may translate into educational inequality.