Nowadays, the complexity of electronic health records (EHRs) requires tools capable of efficiently and accurately extracting and interpreting clinically relevant information to support clinicians. This study explores the use of the Cheshire Cat AI framework, configured with Ollama and using LLaMA3 as a language model, with the main purpose of performing automatic analysis of synthetic EHRs from Kaggle. Through specific structured queries, the model was able to successfully reconstruct patients’ clinical histories and extracted useful data such as diagnoses, treatments, visits, comorbidities and demographic data. A validation process through repeated queries was then performed, which confirmed a high level of accuracy. To preserve data privacy, only synthetic datasets were used in this work. Beyond the simple retrieval of information by means of queries, the study highlights the great potential of language models in clinical decision support. Their ability to interpret large and heterogeneous datasets certainly offers new opportunities to improve diagnostic accuracy, simplify workflows and personalise treatments. Specifically, natural language queries by tools such as Cheshire Cat AI can be used for intelligent support systems that can, for instance, integrate multimodal and real-time data to provide medical recommendations. These results represent a first step towards the exploitation of large language models not only for EHR analysis, but also to assist in clinical decision-making processes in different medical fields and, above all, for the study of specific complex diseases such as rare diseases.