The use of games as a method for planning and designing cities is often associated with visualisation, from simplistic to immersive environments. They can also include complex and sophisticated models which provide an evidence base. The use of such technology as artefacts, aids, or mechanics curates the player experience in different and very often subtle ways, influencing how we engage with (simulated) urban phenomena, and, therefore, how the games can be used. In this article, we aim to explore how different aspects of technology use in city games influence the player experience and game outcomes. The article describes two games built upon the same city gaming framework, played with professionals in Rome and Haifa, respectively. Using a mixed-method, action research approach, the article examines how the high-tech, free form single-player games elicit the mental models of players (traffic controllers and planners in both cases). Questionnaires and the players' reflections on the gameplay, models used, and outcomes have been transcribed and analysed. Observations and results point to several dimensions that are critical to the outcomes of digital city games. Agency, exploration, openness, complexity, and learning are aspects that are strongly influenced by technology and models, and in turn, determine the outcomes of the game. City games that balance these aspects unlock player expertise to better understand the game dynamics and enable their imagination to better negotiate and resolve conflicts in design and planning.