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 This study leverages a critical provocation design approach to examine user interactions with intelligent agents, specifically focusing on how non-conventional agent behaviours impact user perceptions. By embedding playful, challenging, and mischievous elements into the user experience, the research aims to uncover insights that traditional methods might miss. The experimental design involved participants interacting with a trivia game agent named Trivia Friend, which intentionally provided false feedback to provoke reactions and gain insights on user perceptions. Key findings highlight the emotional spectrum elicited by the agent’s behaviour, ranging from frustration and mistrust to amusement and engagement. The study reveals that user perceptions of fairness and communication style are influenced by the agent’s provocations. Furthermore, the research underscores the importance of managing user expectations. A provocative design can stimulate engagement. However, real world implementations of intelligent agents must be designed with fairness and transparency to ensure positive user experiences. The study calls for incorporating efforts towards emotional understanding, clear communication, and ethical considerations when implementing socially capable intelligent agents. This research contributes to the development of adaptive, user-friendly, and ethically sound intelligent AI based agents by offering valuable insights into the complex dynamics of human-agent interactions.