Objective Automated driving is becoming a reality, and such technology raises new concerns about human–machine interaction on road. This paper aims to investigate factors influencing trust calibration and evolution over time. Background Numerous studies showed trust was a determinant in automation use and misuse, particularly in the automated driving context. Method Sixty-one drivers participated in an experiment aiming to better understand the influence of initial level of trust (Trustful vs. Distrustful) on drivers’ behaviors and trust calibration during two sessions of simulated automated driving. The automated driving style was manipulated as positive (smooth) or negative (abrupt) to investigate human–machine early interactions. Trust was assessed over time through questionnaires. Drivers’ visual behaviors and take-over performances during an unplanned take-over request were also investigated. Results Results showed an increase of trust over time, for both Trustful and Distrustful drivers regardless the automated driving style. Trust was also found to fluctuate over time depending on the specific events handled by the automated vehicle. Take-over performances were not influenced by the initial level of trust nor automated driving style. Conclusion Trust in automated driving increases rapidly when drivers’ experience such a system. Initial level of trust seems to be crucial in further trust calibration and modulate the effect of automation performance. Long-term trust evolutions suggest that experience modify drivers’ mental model about automated driving systems. Application In the automated driving context, trust calibration is a decisive question to guide such systems’ proper utilization, and road safety.