Business strategy, operations, communication and technology have converged and resulted in increased demand for business flexibility. Chief Information Officers (CIOs) are particularly challenged because they operate at the intersection between information technology, their organisations, and society. Amidst increasing emphasis on cost-efficiency, information technology resource investment and emergence of new technologies, stakeholders need to understand the most relevant issues within a three-to five-year period. This study was undertaken to contribute to the body of knowledge around key information systems issues in South Africa, with its unique social issues. Thirty-one responses were received from South African CIOs surveyed in late 2004. The top issues were: Security and control, Building a responsive IT infrastructure, IT value management, Service delivery, and Improving IS strategic planning. The ranked list of issues was compared to previous studies, and further analysed by industry and source of IT services (in-house, outsource or combination). Industry and the sourcing of information services were found to have an effect on the ranking of key issues.