Fruitful collaborations rely on cooperative communications, including of contextual cues to incorporate into reasoning. The increasing use of LLMs in collaborative and agentic pipelines raises questions about the extent to which they exhibit these pragmatic capabilities, especially in scenarios where they may not have access to the same information as their collaborators. In this paper, we perform a novel investigation into the pragmatic reasoning capabilities of LLMs in a multi-party collaborative task under partial information conditions. We formalize a notion of collaborative epistemic asymmetry that explicitly connects objective task success to Grice's cooperative principle and empirically assess various LLMs' abilities to act cooperatively as both speakers and listeners, including both prompting and post-training strategies. Our results show that while LLMs exhibit certain pragmatic capabilities in collaborative settings, and these can be elicited through prompting and post-training, they still face challenges in pragmatic communication with incomplete information, and that certain failure modes do correlate with floutings of Grice's maxims that go unrecognized.

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