This article is designed to examine the current situation of urban education in the selected schools in Addis Ababa with the view of establishing specific challenges that confront the schools, as well as, to explore the perception of stakeholders such as school leaders, teachers, students and the parents. To elicit the perceptions of the educational environment, surveys questioning the quantitative data were used in conjunction with interviews collecting the qualitative data. Structural questionnaires were filled by 400 participants who responded to the study purposively; 100 school directors, 100 teachers, 100 students, and 100 parents. Purposeful sampling technique used in the study involved achieving a balance of males and females and representation of 50 schools in Addis Ababa, across the following stakeholders: Further, 10 interview respondents were used to provide qualitative data feedback to enhance the collected data. The sources used for developing this approach include Bronfenbrenner and the Ecological Systems Theory; Levin's Social Justice Theory; Jonassen's Constructivist Learning Theory; and Critical Education Theory. The result depicts moderate perception towards the teaching effectiveness and moderate parental involvement. However, vital concerns were noted with regard to the adequacy of educational material and policy clarity, whereby low mean scores were obtained, pointing out that the current and prospective policies fail to cater for various students' needs. Based on the assessment, the following pivotal steps are suggested for improved resource distribution, class size reduction, effective involvement of key actors in formulation of policies, and better dissemination of the education policies. Applying these recommendations makes it feasible for students to enjoy a better educational climate, with stronger results as well as engagement at the community level. This research advances the study of educational dynamics in so far as it considers stakeholder perceptions as central to the formation and implementation of educational policies and practice. Therefore, closing the stated gaps, this study can be useful for educators, policymakers, and heads of schools who want to enhance students' experiences within educational institutions.