Aim: Road users, such as cyclists and car drivers, are constantly adapting to each other and to the road infrastructure. This study aimed to investigate what trade-offs can be observed when drivers and cyclists adapt to other road users and to the infrastructure. Methods: A semi-controlled study was carried out in an urban traffic environment, where all participants travelled the same route twice, once as a cyclist and once as a car driver. The extended control model was used as an analytical framework to examine how people adapt depending on their main and current road-user role, experiencing different infrastructure and complexity. Results: The results revealed possible trade-offs made while adapting, mainly in relation to rule-following. No differences in adaptive behaviour between people who mostly drive and people who mostly cycle were found. The current situational demands influence both the need to adapt and the adaptation carried out. A more complex traffic environment led to increased information intake, measured by glance behaviour. © 2020, The Author(s).