Passive fatigue during conditional automated driving can compromise driver readiness and safety. This paper presents findings from a test-track study with 40 participants in a real-world rural automated driving scenario. In this scenario, a Large Language Model (LLM) based conversational agent (CA) was designed to check in with drivers and re-engage them with their surroundings. Drawing on in-car video recordings, sleepiness ratings and interviews, we analysed how drivers interacted with the agent and how these interactions shaped alertness. Users found the CA helpful for supporting vigilance during passive fatigue. Thematic analysis of acceptability further revealed three user preference profiles that implicate future intention to use CAs. Positioning empirically observed profiles within existing CA archetype frameworks highlights the need for adaptive design sensitive to diverse user groups. This work underscores the potential of CAs as proactive Human-Machine Interface (HMI) interventions, demonstrating how natural language can support context-aware interaction during automated driving.
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