External human–machine-interfaces (eHMIs) might support the interaction between automated vehicles and pedestrians. The messages conveyed by eHMIs need to be understood quickly and correctly by their addressees. If implemented in the future, pedestrians will repeatedly encounter eHMIs in situations that feature different traffic context. So far, little is known about the influence of contextual cues like regulatory elements or (presumed) model behavior of fellow road users on the comprehension of eHMIs. In order to investigate possible effects of such contextual cues on comprehension, we conducted a picture-based online study among German residents (N = 175). Participants repeatedly interpreted three eHMI icons (“you can cross”, “do not cross”, and “pedestrian detected”) either without any context (control group) or within varying degrees of relevant context (experimental group). Context facilitated comprehensibility in terms of accuracy and subjective certainty. Relevant context was especially beneficial at first encounter. As soon as an icon's meaning was internalized, the necessity of relevant context decreased. The effect of context should therefore be considered in future eHMI research as real-world comprehension might be underestimated otherwise.