Background Research investigating the interactions between cyclists and automated vehicles (AVs) is very scarce. So far, only two photo-based studies (Hagenzieker et al., 2019; Rodríguez Palmeiro, van der Kint, Hagenzieker, van Schagen, & de Winter, 2018) and one study using animated videos (Vlakveld & Kint, 2019) have been performed and have generally found conservative dispositions of cyclists towards AVs. Method The aim of this study was to determine the main factors influencing cyclists’ crossing intentions when interacting with an AV as compared to a conventional vehicle (CV). A 360 video smartphone-based virtual reality experiment was performed and included 16 different scenarios resulting from four factors with two-levels each: vehicle type, gap size, vehicle speed, right of way. Additional factors considered in the study were trust in AVs, cyclists’ self-reported behaviour, Perceived Behavioural Control (PBC), and Perceived Risk (PR). Forty-seven individuals participated in the VR experiment. A multinomial logistic mixed regression model was developed and estimated. Results The primary factors influencing cyclists’ crossing intentions are the distance gap between the cyclist and the vehicle approaching the intersection and the right of way. Neither speed of the approaching vehicle, vehicle appearance, vehicle automation or Trust in AVs had a significant effect on the crossing intentions. Interestingly, participants’ statements whether they trusted AVs as compared to CVs was found to be a better predictor of the crossing intentions compared to their score on the Trust in AVs questionnaire. A positive relation was found between cycling slower or faster and PBC and a negative for PR. Conclusions The results of this study concur with previous studies. Cyclists are still cautious towards automated vehicles and do not adapt their behavior when interacting with them, at this point in time. Therefore, vehicle type and appearance did not have an effect on crossing intentions. However, future exposure to AVs may elicit behavioral adaptation from cyclists. Thus, the long term effects of AVs on cyclists should be studied. The relative trust cyclists have in AVs compared to CVs is more important than the absolute trust.@en