In South Africa the education system ensures that education is available and accessible to every learner. To ensure inclusivity for all learners, the implementation of accommodations for learners with barriers are vital. Research has indicated that the implementation of accommodations can be challenging at times for educators and relevant role players, e.g., policy implementers. The main aim of this study is to explore the systematic challenges when implementing the assessment accommodation policy in independent high schools in a qualitative method. This study applied the interpretivism paradigm to explore the phenomenon under study by applying Bronfenbrenner’s bio-ecological systems theory to explore the challenges experienced. An intensity case study design was selected with six participating independent high schools. Individual semi-structured interviews were conducted with each policy implementer by using intensity sampling. In addition, audio-recordings and a reflection journal were used as a data collection strategy. Using thematic analysis, three main themes emerged from the data, namely: challenges with parent, insufficient internal support for policy implementers, and inadequate services. Each theme was accompanied by a number of sub-themes. Constructed on the research findings, I conclude that when the identified systematic challenges are addressed when implementing inclusive education policies like the IEB’s assessment accommodation policy, then policy implementers, better supported, will be able to ensure that education is accessible to all learners in South Africa. / Psychology of Education / M. Ed. (Psychology of Education)