Human conversation relies heavily on *conversational implicature*, in which speakers convey meanings that are suggested rather than explicitly stated. Although recent large language models (LLMs) 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.

Through a controlled study, we identify a systematic deficiency in the multimodal grounding of Vision Language Models (VLMs). While VLMs can recall factual associations when provided a textual reference to an entity, their ability to do so is significantly diminished when the reference is visual instead. Forcing VLMs to rely on image representations of an entity halves their ability to recall factual knowledge, suggesting that VLMs struggle to link their internal knowledge of an entity with its image representation. We show that such linking failures are correlated with the expression of distinct patterns in model internal states, and that probes on these internal states achieve over 92% accuracy at flagging cases where the VLM response is unreliable. These probes can be applied, without retraining, to identify when a VLM will fail to correctly answer a question that requires an understanding of multimodal input. When used to facilitate selective prediction on a visual question answering task, the probes increase coverage by 7.87% (absolute) while also reducing the risk of error by 0.9% (absolute). Addressing the systematic, detectable deficiency is an important avenue in language grounding, and we provide informed recommendations for future directions.