Planning support tools are developed to ensure streamlined planning process and collaboration. This study explores what planning activities can be supported with planning support tools, how planning support tools fit to the planning support tasks, and what problems occur in performing tasks of planning support. An introduction is given to planning support history, highlighting the evolution of planning support tools, seeking a procedural understanding of planning process and how it can be supported. Functional types and roles of planning support systems (PSS) are introduced, and planning support tools are divided based on types by their specialisation. To assess planning support tools performance I describe planning process tasks that could be supported, as well as user-friendliness of planning support tools. I introduce planning support tools: their interfaces and possible applications in planning process, as well as problems they face performing particular tasks. I explore how tools selected for this study (Cityscope, Cityfier, Tridify, Maptionnaire) can meet the demands of planning support tasks using task technology fit (TTF) methodology, results are summarised in concluding table.