Multi-modal Large Language Models (MLLMs) have made substantial advances on benchmarks, yet their real-world effectiveness remains uncertain. This gap stems from the fundamental misalignment between benchmarks in controlled, static settings and the dynamic, interactive, and contextualized nature of real-world applications. To bridge this gap, we propose CEDI (Contextualized Evaluation of MLLMs through Dynamic, multi-round Interactions), a framework that recasts evaluation as a three-party interaction between an evaluatee model, an automated examiner, and a grader. The examiner conducts multi-turn, semi-structured conversations guided by a graph-based representation of the task. By navigating state-space transitions, CEDI deploys diverse strategies, from clarification requests to adversarial probes, to elicit performance evidence. We apply CEDI to visual hallucinations. Empirical results across multiple models, diverse settings, datasets, and domains show that contextualized, interactive evaluations reveal not only significantly more hallucinations than conventional static evaluation but also ones that more closely resemble those arising in practical use cases. We further show that hallucinations often accumulate over long contexts, through self-reinforcing dialogue history, and models are particularly vulnerable to questions requiring premise rejection or refusal. Together, these findings highlight CEDI as a step toward realistic, systematic, and ecologically valid assessments of MLLMs' capabilities. Code is available at github.com/williamium3000/cedi.

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