Abstract: The objective of the study was to determine challenges affecting effective implementation of the 2020 school re – entry policy guidelines in Narok County, Kenya. The study targeted 132 girls and mixed public secondary schools in Narok County with a sample size of 20 schools that were selected using multistage and simple random sampling techniques. A participatory approach that engaged diverse stakeholders including school principals, teachers, form three students for the year 2022, teenage mothers, expectant girls, parents and guardians, Sub County Directors of Education, Children Department Officers, County Education Gender Officer and representatives of Non – Governmental Organizations was used. The survey included 720 respondents chosen using probability and non-probability sampling procedures. The study was anchored on theoretical principles of General Systems Theory. Convergence parallel design with cross sectional and hermeneutic phenomenology strands guided the study. A Questionnaire was used to collect quantitative data while interview guides and FGD discussion guides collected qualitative data. Descriptive statistics was used to analyse quantitative data while thematic analysis was used to analyse qualitative data. The evaluation established that challenges that affect effective implementation of the re-entry policy in Narok County include unfavorable school environments, lack of psychosocial support to the affected girls, poor record keeping of drop out and re-entry rates, inconsistency in the implementation of the policy at the school level, retrogressive cultural practices, limited support from baby fathers and parents and lack of enforcement by the Ministry of Education. The evaluation makes key recommendations including freeing school environment of stigma, integration of mental and psychosocial support to the policy, strengthening record keeping, undertaking frequenting monitoring to track implementation progress and eliminating retrogressive social and cultural norms. 

Key words: Challenges, Policy implementation, 2020 School re-entry guidelines, Teenage mothers, Expectant girls