Situation awareness, ones understanding of ‘what is going on’, is a critical commodity for road users. Although the concept has received much attention in the driving context, situation awareness in vulnerable road users, such as cyclists, remains unexplored. This paper presents the findings from an exploratory on-road study of cyclist situation awareness, the aim of which was to explore how cyclists develop situation awareness, what their situation awareness comprises, and what the causes of degraded cyclist situation awareness may be. Twenty participants cycled a pre-defined urban on-road study route. A range of data were collected, including verbal protocols, forward scene video and rear video, and a network analysis procedure was used to describe and assess cyclist situation awareness. The analysis produced a number of key findings regarding cyclist situation awareness, including the potential for cyclists’ awareness of other road users to be degraded due to additional situation awareness and decision making requirements that are placed on them in certain road situations. Strategies for improving cyclists’ situation awareness are discussed.