Flout at Your Own Risk: LLMs Struggle with Pragmatic Cooperativity Under Epistemic Asymmetry

As LLM-based agents with user-instructed goals are becoming widely deployed, they increasingly encounter each other in strategic interactions, and face challenges of finding mutually beneficial outcomes. Prior literature has argued that cooperation problems such as the Prisoner's Dilemma are resolvable in settings where agents know they follow very similar decision making patterns, as for example in monocultural AI ecosystems. Following that line of work, this paper introduces the first framework for evaluating LLM decision making when agents are provided with graded similarity signals. Among our findings, we establish that different LLM models vary drastically in how they navigate similarity signals, with some modern models showing consistent behavior across cooperation problems, payoff structures, and prompt framing. Perhaps surprisingly, our experiments also show that the dataset based on which the similarity signal is computed has small to no impact on induced cooperation, and that LLM models systematically self-identify as highly similar when asked to evaluate another model's chain-of-thought reasoning by themselves. Finally, we develop an LLM-behavioral-game-theoretic model that captures some of their reasoning rationale, and show that it can support cooperative outcomes in equilibrium under sufficiently high similarity scores.

Large language models (LLMs) are increasingly studied as repositories of linguistic knowledge. In this line of work, models are commonly evaluated both as generators of language and as judges of linguistic output, yet these two roles are rarely examined in direct relation to one another. As a result, it remains unclear whether success in one role aligns with success in the other. In this paper, we address this question for pragmatic competence by comparing LLMs' performance as pragmatic listeners, judging the appropriateness of linguistic outputs, and as pragmatic speakers, generating pragmatically appropriate language. We evaluate multiple open-weight and proprietary LLMs across three pragmatic settings. We find a robust asymmetry between pragmatic evaluation and pragmatic generation: many models perform substantially better as listeners than as speakers. Our results suggest that pragmatic judging and pragmatic generation are only weakly aligned in current LLMs, calling for more integrated evaluation practices.

LLMs are increasingly presented as collaborators in programming, design, writing, and analysis. Yet the practical experience of working with them often falls short of this promise. In many settings, users must diagnose misunderstandings, reconstruct missing assumptions, and repeatedly repair misaligned responses. This poster introduces a conceptual framework for understanding why such collaboration remains fragile. Drawing on a constructivist grounded theory analysis of 16 interviews with designers, developers, and applied AI practitioners working on LLM-enabled systems, and informed by literature on human-AI collaboration, we argue that stable collaboration depends not only on model capability but on the interaction's grounding conditions. We distinguish three recurrent structures of human-AI work: one-shot assistance, weak collaboration with asymmetric repair, and grounded collaboration. We propose that collaboration breaks down when the appearance of partnership outpaces the grounding capacity of the interaction and contribute a framework for discussing grounding, repair, and interaction structure in LLM-enabled work.