Applying geographic information (GI) technologies to facilitate managerial and operational processes in urban management is a widely known approach. However, planning practice seems to lag behind in their incorporation. While the academic world has embraced planning support systems (PSS), their use in planning practice remains sporadic and limited. This disconnect creates a gap between the PSS knowledge produced in academic settings, with regard to collaborative planning and decision-making, and the unrealized potential of applying PSS in planning cultures that lack collaborative approaches. This chapter aims to address the gap between academia and planning practice by incorporating the practitioner discussions regarding the utility of PSS in a planning process. It elaborates a real-life case application that explored the usability of PSS in a collaborative planning approach. Through this contribution, we aim to strengthen the relationship and foster interaction between academia and practice.