An e-Learning project has been rolled out in Gauteng schools in an attempt to improve the quality of education and move towards paperless classrooms. The purpose of this study was to investigate the challenges faced by Tshwane South Secondary Schools associated with the implementation of the e-Learning project with a view to suggest possible solutions. The study followed a qualitative research approach with a case study research design. The study population consisted of teachers, school management team (SMT), and learners. Purposive sampling was used to select three teachers, six learners and three school management team members of the schools' e-Learning committees. Data was collected through individual semi-structure interviews and focus group interview. The Analysis, Design, Development, Implementation, and Evaluation model (ADDIE model) was used to provide a theoretical perspective on how instructional designers, training developers, and educators should design and develop a program such as e-Learning. The data was analysed using a thematic approach. The study found that teachers were not adequately trained prior to the implementation of e-Learning, which impacted negatively on the project. Teachers had difficulty in operating the smartboards and accessing the learning resources that has been loaded in the smartboards which affected the implementation of the project. The study concluded that poor planning on the site of Department of Basic Education has resulted into challenges that hampered the implementation of e-Learning. The study recommends extensive training of both learners and teachers in the use of e-Learning.