Interpreter agents built on machine translation (MT) increasingly mediate live conversation between people who do not share a language, yet we still evaluate them with metrics built for isolated sentences, which measure fidelity rather than whether communication succeeds. We introduce a reusable three-layer checklist-and-judge framework that evaluates interpreter-mediated conversation across semantic, pragmatic, and cultural-social dimensions, covering the naturalness, intent, and social appropriateness that fidelity metrics leave unmeasured. It runs in both single-turn and interactive multi-turn settings, where simulated users reply to translated messages as the conversation unfolds and each turn is scored alongside the conversation as a whole. We extensively validate it through controlled perturbations, cross-judge comparisons, and human annotations. Our main single-turn benchmark evaluates 10 interpreter setups across Arabic, Bengali, Indonesian, and Korean from 5,624 OpenSubtitles-derived scenarios spanning 12 translation directions, and our multi-turn study covers all 6 language pairs in scripted and live modes. Results show a consistent decline from semantic to pragmatic and cultural-social success, while conventional MT metrics overlook failures among stronger interpreters, and prompt ablations show that scenario context, structured instructions, and cultural context improve communicative success, although gains vary across setups. Our work thus provides an evaluation framework and benchmark for interpreter agents in conversation, and highlights the importance of communicative success alongside existing translation metrics.

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