Aim <p>This study aims to evaluate the potential of AI-based chatbots in assisting with clinical decision-making in the management of medically complex patients in oral surgery.</p> Materials and methods <p>A team of oral and maxillofacial surgeons developed a pool of open-ended questions <i>de novo</i>. The validity of the questions was assessed using Lawshe’s Content Validity Index. The questions, which focused on systemic diseases and common conditions that may raise concerns during oral surgery, were presented to ChatGPT 3.5 and Claude-instant in two separate sessions, spaced one week apart. Two experienced maxillofacial surgeons, blinded to the chatbots, assessed the responses for quality, accuracy, and completeness using a modified DISCERN tool and Likert scale. Intraclass correlation, Mann-Whitney U test, skewness, and kurtosis coefficients were employed to compare the performances of the chatbots.</p> Results <p>Most responses were high quality: 86% and 79.6% for ChatGPT, and 81.25% and 89% for Claude-instant in sessions 1 and 2, respectively. In terms of accuracy, ChatGPT had 92% and 93.4% of its responses rated as completely correct in sessions 1 and 2, respectively, while Claude-instant had 95.2% and 89%. For completeness, ChatGPT had 88.5% and 86.8% of its responses rated as adequate or comprehensive in sessions 1 and 2, respectively, while Claude-instant had 95.2% and 86%.</p> Conclusion <p>Ongoing software developments and the increasing acceptance of chatbots among healthcare professionals hold promise that these tools can provide rapid solutions to the high demand for medical care, ease professionals’ workload, reduce costs, and save time.</p>