<p>This study investigates how urban configuration, the spatial arrangement, and characteristics of the built environment, particularly the contrast between high-rise and low-rise settings, influence wayfinding propensity. Building on Credé and Fabrikant [Let’s put the skyscrapers on the display—decoupling spatial learning from working memory. In: Freksa C, Winter S (eds) Proceedings of workshops and posters at the 13th international conference on spatial information theory (COSIT 2017). Springer, Cham, pp 163–170, 2018] assertion that global landmarks improve wayfinding by reducing cognitive load, this research explores how landmarks interact with urban configurations to affect individuals’ wayfinding. Using three virtual environment configurations in the video game Grand Theft Auto V, the study evaluates the wayfinding performance of 50 participants. The results highlight four significant findings: first, high-rise environments significantly increase the perception and importance of city image elements and urban design qualities for wayfinding; second, analysis of variance revealed statistically significant differences in wayfinding times between high-rise and low-rise environments, showing the critical role of urban configuration in shaping navigation efficiency; third, multiple regression analysis demonstrated that improvements in individuals’ wayfinding time and route knowledge are more pronounced in high-rise settings; and lastly, route-following behavior varies notably across configurations, highlighting differences in the perception of city image elements. Collectively, the findings of this study offer valuable insights into the influence of urban configuration, image elements, and urban design qualities on wayfinding, contributing to the development of more intuitive urban areas that enhance navigational efficiency and user experience.</p>