Urbanization, particularly in developing countries, has brought about opportunities and major challenges. Similarly, the new urban agenda that is indicator-centric has forced planners to change planning by utilizing information and communications technologies. This chapter explores the level of use of planning support systems (PSS) and e-planning as well as the challenges in four cities – Johannesburg and Ekurhuleni in South Africa, and Harare and Bulawayo in Zimbabwe – allowing comparisons to be made between cities at various stages in the adoption of PSS and e-planning. A survey that targeted practitioners in the planning departments of each city was conducted to gauge the level of PSS and e-planning application. How the citizens utilized and engaged with e-planning and PSS was also assessed. The results indicate that there is a high uptake and potential for e-planning by citizens in the planning process; however, there is limited use of PSS in the three metropolitan municipalities. Challenges such as lack of training and resources, poor organizational culture and insufficient education for planners have inhibited the application of PSS in cities of the developing world. Nevertheless, the increased penetration of smartphones as well as the internet and the eagerness of citizens to adopt e-planning bodes well for improving e-planning and its adoption in future.