With the increasing use of phone-based ride-hailing apps, concerns have arisen regarding road safety and driver distraction. Despite the recognized safety risks of driver distraction, limited research has explored how distractions from various ride-hailing systems affect drivers in the taxi industry. To close this gap, the current research utilized a driving simulator experiment involving 51 male taxi drivers in two road environments (urban street and motorway) and three distracted driving conditions (no distraction, auditory distraction via radio dispatching system, and visual-manual distraction via mobile application). A car-following scenario with sudden brake events was incorporated into the experiments because this is a typical safety–critical situation where attention will determine the outcome. The collected performance indicators include brake reaction time, time headway, and car-following distance. The grouped random parameters Weibull accelerated failure time model was applied to model the duration data under different road conditions. The brake reaction time and time headway are dependent variables, while the car-following distance is a covariate in the models. The results indicate that although taxi drivers show longer brake reaction time when distracted by mobile app and radio system, this does not necessarily equate with greater risk or reduced safety since they compensate for the risk of rear-end crashes by maintaining a longer time headway. In general, taxi drivers’ brake reaction time and time headway are more profoundly affected by mobile apps when distracted in both urban and motorway scenarios. This highlights the elevated risks associated with such technologies. In addition, significant interaction effects revealed the observed heterogeneity, which suggests that drivers’ personal characteristics influence the relationship between distraction type and driving performance. This research provides valuable insights for designing safer ride-hailing operations and systems.