Open Source Software (OSS) presents many benefits to both the private and the public sectors, and has proven to be a viable solution in schools. Although a policy mandating the use of OSS exists in the Western Cape province of South Africa, very few schools in the province have adopted OSS. The education system in South Africa is currently facing a crisis because of its inability to provide quality education, and its lack of funds. The Western Cape recently signed a Microsoft Schools Agreement. This study aimed at gaining insights into the factors influencing or inhibiting OSS adoption within the Western Cape Schools Environment. In-depth interviews were conducted with senior staff in the Department of the Premier, and the Department of Education, as well as users at school level. The Technology-Organisation-Environment (TOE) framework was employed to organise the data, while thematic analysis was used to uncover themes and patterns in the data. Significant factors that emerged as positive influences on the adoption of OSS included cost, performance and positive attitudes. The negative influences that emerged included compatibility, lack of resources and time, and lack of support. Recommendations for the negative influences were highlighted, and include research and development, employment of additional resources, on-going support, and training. The study contributes to existing knowledge, by extending the TOE framework through the inclusion of the "Individual" element.