To ensure traffic flow and road safety in automated driving, external human–machine interfaces (eHMIs) could prospectively support the interaction between automated vehicles (AVs; SAE Level 3 or higher) and pedestrians if implicit communication is insufficient. Particularly elderly pedestrians (≥65 years) who are notably vulnerable in terms of traffic safety might benefit of the advantages of additional signals provided by eHMIs. Previous research showed that eHMIs were assessed as useful means of communication in AVs and were preferred over exclusively implicit communication signals. However, the attitudes of elderly users regarding technology usage and acceptance are ambiguous (i.e., less intention to use technology vs. a tendency toward overreliance on technology compared to younger users). Considering potential eHMI malfunctions, an appropriate level of trust in eHMIs is required to ensure traffic safety. So far, little research respected the impact of multiple eHMI malfunctions on participants’ assessment of the system. Moreover, age effects were rarely investigated in eHMIs. In the current monitor-based study, N = 36 participants (19 younger, 17 elderly) repeatedly assessed an eHMI: During an initial measurement, when encountering a valid system and after experiencing eHMI malfunctions. Participants indicated their trust and acceptance in the eHMI, feeling of safety during the interaction and vigilance toward the eHMI. The results showed a positive effect of interacting with a valid system that acted consistently to the vehicle’s movements compared to an initial assessment of the system. After experiencing eHMI malfunctions, participants’ assessment of the system declined significantly. Moreover, elderly participants assessed the eHMI more positive across all conditions than younger participants did. The findings imply that participants considered the vehicle’s movements as implicit communication cues in addition to the provided eHMI signals during the encounters. To support traffic safety and smooth interactions, eHMI signals are required to be in line with vehicle’s movements as implicit communication cues. Moreover, the results underline the importance of calibrating an appropriate level of trust in eHMI signals. An adequate understanding of eHMI signals needs to be developed. Thereby, the requirements of different user groups should be specifically considered.