Human conversation relies heavily on conversational implicature, in which speakers convey meanings that are suggested rather than explicitly stated. Although recent large language models exhibit strong conversational fluency, they remain unreliable when interpretation depends on reasoning that integrates social and contextual cues, a process rarely articulated in text. We introduce DRinQ, a benchmark for evaluating pragmatic reasoning about conversational implicature in question utterances, designed to isolate pragmatic variation while holding each question's surface form fixed. To support scalable evaluation, we propose a semi-automated pipeline that produces question-context-interpretation instances with systematic variation. Across evaluations, we find a consistent generation-inference asymmetry: while state-of-the-art models can generate plausible pragmatic scenarios when guided, they often fail to recover the intended implication at inference time. For smaller models, structured prompting improves alignment with human judgments. A comparative writing study further reveals complementary strengths: human authors tend to produce safer, predictable contexts, whereas models generate varied scenarios with interpretations that sometimes exceed contextual support. These findings highlight persistent challenges in modeling conversational implicature and motivate more context-sensitive evaluation frameworks.
Presupposition projection in conditionals is central to theories of meaning and pragmatics, yet it remains largely unevaluated in large language models. We address this gap through a parallel behavioral study comparing human judgments and LLM predictions on a normed dataset of conditional sentences that controls the relation between the antecedent and the projected presupposition. We collect likelihood ratings from 120 participants and four LLMs under matched contextual conditions. Results show that humans integrate probabilistic and pragmatic cues in their judgment, whereas LLMs show variable alignment with human patterns. Using a linguistically motivated checklist within an LLM-as-a-Judge framework, we further evaluate model reasoning. We observe models that best match human ratings often lack coherent pragmatic reasoning, while models with stronger reasoning produce less human-like judgments. These findings suggest that LLMs' performance on such tasks may result from surface pattern matching rather than pragmatic competence. Our findings highlight the importance of benchmarks grounded in linguistic theory for comparing humans and models.
Humans effortlessly go beyond literal meanings: If you mow the lawn, I will give you fifty dollars, is typically understood as implying that the speaker will pay only if the lawn is mowed, whereas If you are hungry, there is pizza in the oven implies that pizza is available regardless of the hearers hunger. Large Language Models - LLMs - show human-like performance on many tasks, yet it remains unclear whether they reason like humans. To address this, we conducted a population-matching experiment assessing how twentyfive LLMs compute conditional inferences across four languages, compared to an equal number of humans per language. We find that humans enrich logical reasoning through pragmatic inferences across languages. Model behavior is more variable. Some LLMs perfectly follow the truth-table of conditionals but they ignore pragmatic inferences, while others deviate from the truth-table, adhering to a single interpretation across the board, thus reflecting accurate rule-based processing but not human-like reasoning. Overall, LLMs are accurate semantic operators, but fail to capture the pragmatic enrichments characteristic of human reasoning. Crucially, LLM accuracy is neither predicted nor boosted by open vs. closed status, training orientation, or architecture type, suggesting that pragmatic reasoning is still an emerging ability in the cognitive toolkit of artificial systems.
Paolo Morosi, Nikoleta Pantelidou, Fritz Günther +2
We introduce DiscoTrace, a method to identify the rhetorical strategies answerers use when responding to information-seeking questions. DiscoTrace represents answers as a sequence of question-related discourse acts paired with interpretations of the original question, annotated on top of rhetorical structure theory parses. Applying DiscoTrace to answers from nine different communities reveals that communities have diverse preferences for answer construction. In contrast, LLMs do not exhibit rhetorical diversity in their answers, even when prompted to mimic specific human community answering guidelines. LLMs also systematically opt for breadth, addressing interpretations of questions that human answerers choose not to address. The rich, community-sensitive answering behavior structurally revealed by DiscoTrace can guide the development of pragmatic LLM answerers that are more attuned to contextual information needs.
Neha Srikanth, Jordan Boyd-Graber, Rachel Rudinger