In law, lore, and everyday life, loopholes are commonplace. When people exploit a loophole, they understand the intended meaning or goal of another person, but choose to go with a different interpretation. Past and current AI research has shown that artificial intelligence engages in what seems superficially like the exploitation of loopholes, but this is likely anthropomorphization. It remains unclear to what extent current models, especially Large Language Models (LLMs), capture the pragmatic understanding required for engaging in loopholes. We examined the performance of LLMs on two metrics developed for studying loophole behavior in humans: evaluation (ratings of trouble, upset, and humor), and generation (coming up with new loopholes in a given context). We conducted a fine-grained comparison of state-of-the-art LLMs to humans, and find that while many of the models rate loophole behaviors as resulting in less trouble and upset than outright non-compliance (in line with adults), they struggle to recognize the humor in the creative exploitation of loopholes in the way that humans do. Furthermore, only two of the models, GPT 3 and 3.5, are capable of generating loopholes of their own, with GPT3.5 performing closest to the human baseline.

Systems that automatically define unfamiliar terms hold the promise of improving the accessibility of scientific texts, especially for readers who may lack prerequisite background knowledge. However, current systems assume a single “best” description per concept, which fails to account for the many ways a concept can be described. We present ACCoRD, an end-to-end system tackling the novel task of generating sets of descriptions of scientific concepts. Our system takes advantage of the myriad ways a concept is mentioned across the scientific literature to produce distinct, diverse descriptions oftarget concepts in terms of different reference concepts. In a user study, we find that users prefer (1) descriptions produced by our end-to-end system, and (2) multiple descriptions to a single “best” description. We release the ACCoRD corpus which includes 1,275 labeled contexts and 1,787 expert-authored concept descriptions to support research on our task.