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Drawing on key concepts of semantics and pragmatics, we analyze interactions with two state-of-the-art systems, namely, ChatGPT and Claude. Through qualitative analysis of prompt\u2013response interactions, we assess how these systems manage meaning and social nuance. Our findings highlight significant limitations in AI\u2019s pragmatic competence, especially in grounding communication and interpreting implicit cues. We argue that naturalness in human\u2013AI interaction is not a fixed standard based on human norms, but a socially negotiated and context-dependent construct. Instead of designing AI to imitate human behavior perfectly, we advocate for redefining naturalness in terms of communicative functionality, user expectations, and adaptive interactional strategies. This reconceptualization foregrounds the importance of designing AI systems that foster trust, clarity, and usability within their specific social roles.<\/jats:p>","DOI":"10.1007\/s00146-025-02595-1","type":"journal-article","created":{"date-parts":[[2025,9,20]],"date-time":"2025-09-20T16:28:45Z","timestamp":1758385725000},"page":"1053-1062","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Do chatbots dream of AI sheep? A semantic\u2013pragmatic investigation of \"naturalness\" in human\u2013AI interaction"],"prefix":"10.1007","volume":"41","author":[{"given":"Iuliia","family":"Lysova","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lara","family":"Ahmed","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bethan","family":"Cunningham","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yonghua","family":"Huang","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Martina","family":"Wiltschko","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2025,9,20]]},"reference":[{"key":"2595_CR1","volume-title":"How to do things with words","author":"JL Austin","year":"1962","unstructured":"Austin JL (1962) How to do things with words. 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