Real-world health questions from patients often unintentionally embed false assumptions or premises. In such cases, safe medical communication typically involves redirection: addressing the implicit misconception and then responding to the underlying patient context, rather than the original question. While large language models (LLMs) are increasingly being used by lay users for medical advice, they have not yet been tested for this crucial competency. Therefore, in this work, we investigate how LLMs react to false premises embedded within real-world health questions. We develop a semi-automated pipeline to curate MedRedFlag, a dataset of 1100+ questions sourced from Reddit that require redirection. We then systematically compare responses from state-of-the-art LLMs to those from clinicians. Our analysis reveals that LLMs often fail to redirect problematic questions, even when the problematic premise is detected, and provide answers that could lead to suboptimal medical decision making. Our benchmark and results reveal a novel and substantial gap in how LLMs perform under the conditions of real-world health communication, highlighting critical safety concerns for patient-facing medical AI systems. Code and data are available at https://github.com/srsambara-1/MedRedFlag.

People are increasingly seeking healthcare information from large language models (LLMs) via interactive chatbots, yet the nature and inherent risks of these conversations remain largely unexplored. In this paper, we filter large-scale conversational AI datasets to achieve HealthChat-11K, a curated dataset of 11K real-world conversations composed of 25K user messages. We use HealthChat-11K and a clinician-driven taxonomy for how users interact with LLMs when seeking healthcare information in order to systematically study user interactions across 21 distinct health specialties. Our analysis reveals insights into the nature of how and why users seek health information, such as common interactions, instances of incomplete context, affective behaviors, and interactions (e.g., leading questions) that can induce sycophancy, underscoring the need for improvements in the healthcare support capabilities of LLMs deployed as conversational AI. We release code and artifacts to retrieve our analyses and combine them into a curated dataset for further research.