Often a Grade 12 certificate is perceived as a passport to tertiary education and the minimum requirement to enter the world of work. In spite of its importance, many students do not make this milestone in South Africa. It is important to find out why so many students still fail in spite of transformation in the education system in the post-apartheid era. Given the complexity of education and its context, this study adopted a case study design to examine one historically underperforming high school in Bushbuckridge, Mpumalanga Province, South Africa in 2013. The aim was to gain a understanding of the inner and outer school contextual factors associated with the high failure rate among Grade 12 students. Government documents and reports were consulted to identify factors in the district and the village surrounding the school and a student survey was conducted to identify school, home and student factors. The randomly-sampled half of the population of Grade 12 students (53) participated in the survey and quantitative data are analyzed using descriptive statistical methods. The findings showed that a host of factors is at play. The school is located in a village within a municipality which has been one of the poorest three municipalities in South Africa and the lowest Grade 12 pass rate in the Mpumalanga province. Moreover, over half of the families of the students are single parents, 43% are unemployed and the majority has a low level of education. In addition, most families (83%) do not have basic study materials such as a dictionary, books, tables, and chairs. A significant number of students (70%) are over-aged (+19 years old); close to half of them (49%) are grade repeaters. The school itself lacks essential resources, namely computers, science laboratories, library, and enough furniture and textbooks. Moreover, teaching and learning are negatively affected by the teachers’ occasional absenteeism, inadequate lesson preparation, and poor communication skills. Overall, the continuous low performance of students in this school mirrors the vicious circle of multiple negative conditions present within and outside of the school. The complexity of factors associated with the underperformance of Grade 12 students in this school calls for a multi-dimensional intervention from government and stakeholders. One important intervention should be the placement of over-aged students and grade-repeaters in suitable educational institutions for the benefit of other students.