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Despite the prevalence of such ambiguities in practice, existing agent benchmarks largely assume unambiguous, well-specified policies, leaving a critical evaluation gap. We introduce DRIP-R, a benchmark that systematically exploits real-world retail policy ambiguities to construct scenarios in which no single correct resolution exists. DRIP-R comprises a curated set of policy-ambiguous return scenarios paired with a realistic customer personas, a full-duplex conversational simulation with tool-calling capabilities and a multi-judge evaluation framework covering policy adherence, dialogue quality, behavioral alignment, and resolution quality. 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DRIP-R comprises a curated set of policy-ambiguous return scenarios paired with a realistic customer personas, a full-duplex conversational simulation with tool-calling capabilities and a multi-judge evaluation framework covering policy adherence, dialogue quality, behavioral alignment, and resolution quality. 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