The aim of this study was to investigate the schooling experiences of four orphaned learners at Mandini Secondary School in the Maluti District of Education in the Eastern Cape. The study adopted a qualitative research methodology and a phenomenological research design. Purposive sampling was adopted and the tape recorded narrative responses of all four respondents, were obtained from the use of in-depth phenomenological unstructured interviews. The respondents were four orphaned children (two males and two females) between the ages of fifteen and twenty years. The study used the Social Rupture Theory as lenses of analysis of the findings. This was considered a very sensitive topic because the respondents had to relate issues which could result in them reliving traumatic experiences. As a result more attention was paid on ethical issues and making the respondents feel comfortable. The respondents were capable of distinguishing between their quality of life while their parents were still alive and well; when they (the parent[s]) became sick and when they eventually died. Furthermore, the respondents highlighted the negative effects of parental absence in their education. In addition, these orphaned children formed relationships with the school community after their parents’ death which, to some extent, had a positive effect on their schooling. Based on these findings the study suggests that educators need to be trained in diagnosing psycho-social problems and given skills to deal with them. Similarly, short courses should be organized for guardians and community development workers in identifying and counseling of problems.