Interest in the concept of AI-driven harmful manipulation is growing, yet current approaches to evaluating it are limited. This paper introduces a framework for evaluating harmful AI manipulation via context-specific human-AI interaction studies. We illustrate the utility of this framework by assessing an AI model with 10,101 participants spanning interactions in three AI use domains (public policy, finance, and health) and three locales (US, UK, and India). Overall, we find that that the tested model can produce manipulative behaviours when prompted to do so and, in experimental settings, is able to induce belief and behaviour changes in study participants. We further find that context matters: AI manipulation differs between domains, suggesting that it needs to be evaluated in the high-stakes context(s) in which an AI system is likely to be used. We also identify significant differences across our tested geographies, suggesting that AI manipulation results from one geographic region may not generalise to others. Finally, we find that the frequency of manipulative behaviours (propensity) of an AI model is not consistently predictive of the likelihood of manipulative success (efficacy), underscoring the importance of studying these dimensions separately. To facilitate adoption of our evaluation framework, we detail our testing protocols and make relevant materials publicly available. We conclude by discussing open challenges in evaluating harmful manipulation by AI models.

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