Planning has failed to exert effective influence on the growth of human settlements in Ghana. As a result, the growth of cities has been chaotic. The district assemblies, which are the designated planning authorities, are commonly blamed for this failure, yet little attention has been given to district assemblies’ perspectives of what factors lead to failures in planning. This paper attempts to fill this gap. Drawing on fieldwork in Ghana, it argues that, from the perspective of district assemblies, five major challenges inhibit planning, namely: an inflexible land ownership system, an unresponsive legislative framework, undue political interference, an acute human resource shortage, and the lack of a sustainable funding strategy. The paper concludes with proposals for reforming the planning system in Ghana.