Planning Support Systems (PSS) are a promising tool for involving stakeholders in urban adaptation workshops. Past research has focused on the use and added value of PSS. While earlier studies have widely acknowledged the importance of context in determining the effectiveness of PSS, there has so far been no dedicated study of the influence of context on the use and added value of these tools in real planning workshops. To address this gap, we made an in-depth exploratory case study of a PSS, called the Adaptation Support Tool (AST), used in an adaptation planning workshop in Guayaquil, Ecuador. The workshop used the AST to support collaborative spatial planning for urban water management, at the neighbourhood scale. Interviews, questionnaires, observations and document review were used to investigate the influence of three contextual factors on the use and added value of the AST. The studied contextual factors are: 1) the style of tool use, 2) the phase of planning, and 3) the local project setting. Our findings indicate that the style of tool use and the local project setting were the most important contextual factors in determining the use and added value of the AST during the workshop. Meanwhile, the phase of planning appears to be critical for achieving impacts at the project level. This exploratory case study is a modest first contribution to understanding the influence of context on the use and added value of PSS in practice. Nevertheless, the findings indicate that further exploration of this topic could offer important insights to PSS use in practice. The influence of context on the use and added value of Planning Support Systems in workshops: an exploratory case study of climate adaptation planning in Guayaquil, Ecuador.