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Understanding sentence meanings and updating information states appropriately across time – what we call “situational understanding” (SU) – is a critical ability for human-like AI agents. SU is essential in particular for chat models, such as ChatGPT, to enable consistent, coherent, and effective dialogue between humans and AI. Previous works have identified certain SU limitations in non-chatbot Large Language models (LLMs), but the extent and causes of these limitations are not well understood, and capabilities of current chat-based models in this domain have not been explored. In this work we tackle these questions, proposing a novel synthetic environment for SU testing which allows us to do controlled and systematic testing of SU in chat-oriented models, through assessment of models’ ability to track and enumerate environment states. Our environment also allows for close analysis of dynamics of model performance, to better understand underlying causes for performance patterns. We apply our test to ChatGPT, the state-of-the-art chatbot, and find that despite the fundamental simplicity of the task, the model’s performance reflects an inability to retain correct environment states across time. Our follow-up analyses suggest that performance degradation is largely because ChatGPT has non-persistent in-context memory (although it can access the full dialogue history) and it is susceptible to hallucinated updates – including updates that artificially inflate accuracies. Our findings suggest overall that ChatGPT is not currently equipped for robust tracking of situation states, and that trust in the impressive dialogue performance of ChatGPT comes with risks. We release the codebase for reproducing our test environment, as well as all prompts and API responses from ChatGPT, at https://github.com/yangalan123/SituationalTesting.