This thesis focuses on the planning support systems (PSS) that are currently being applied in Dutch urban development practice. The use of PSS can support the complex urban development processes by giving insight into the urban processes by structuring and visualising spatial data, and also by supporting the communication and collaboration between stakeholders through interactive workshops. Nevertheless, after years of development, PSS are still scarcely applied in planning practice. One of the bottlenecks to its widespread use is the unfamiliarity of PSS to its potential users. Therefore, the aim of this research is to increase our understanding of the constraints and benefits of planning support systems; to increase our comprehension of their role in the Dutch urban development processes; and to provide insights into the different factors that influence the perceived usefulness of these applications in the decision-making process in urban development in the Netherlands. Next to a literature review, four case studies were executed using two different PSS: the MKP-MapTable of the Province of Utrecht and Urban Strategy of TNO. Additionally, the use of Tygron, Planmaat and Play the City is outlined based on semi-structured interviews with the developers to illustrate the broad variety of planning support systems. The results of these case studies have led to recommendations about the use of PSS in the urban redevelopment project Buiksloterham in Amsterdam. The outcomes are explained by using systems theory. The case studies illustrate that it still takes much preparation time to adapt PSS to the specific spatial issue. Although PSS can be used individually, the application of PSS is especially suitable for complex, integral urban development processes that are characterised by open group decision-making. PSS process explicit knowledge that can determine the feasibility of a plan, while tacit knowledge can be shared during the workshop in order to determine the desirability of a plan. PSS are not able to visualise all the effects of urban development plans, due to the complex relationships between the different elements of urban development. Therefore, PSS advise stakeholders, but stakeholders do not have to abide by the result. PSS need to become more flexible in order to deal with the new insights of stakeholders during the planning process. In Buiksloterham, PSS are especially usefull in sharing information between different stakeholders in order to create a mutual understanding and a broad support on how Buiksloterham should be developed.