Language models are increasingly mediating information access to end users, urging a systematic evaluation of their responses for a fair and reliable information ecosystem. Existing evaluations, however, are often topic-specific or synthetic, limiting their ability to capture the complexity of "in the wild" information-seeking queries and the risks present in model responses. To address this gap, we introduce WildSEEK, a manually annotated dataset of 3k information-seeking queries from real user interactions, and an evaluation framework for LLM-generated responses. WildSEEK includes annotations for risk-sensitive domains (e.g. health and financial information), and distinguishes factoid queries from analytical queries which seek responses beyond facts. We train classifiers on WildSEEK to analyze more than 1.8M realistic user queries. We find that over a third of information-seeking queries are high-risk and more often analytical. Our findings show that LLM responses fail more often in four criteria: sycophantic behavior, overreliance, a default US-centric perspective, and poor handling of vulnerable populations -- with failure rates being mostly higher for analytical queries. By providing methods to monitor the reliability, safety, and fairness of LLM behavior, our dataset and evaluation framework offer an empirical foundation for the broader question of how these systems should behave as they take on a growing role in information access.
Large language models (LLMs) are widely used to fulfill users' information needs; users ask LLMs about the weather, pose educational questions, and consult them for legal assistance. One particularly understudied area is digital security and privacy (S&P), where users may seek LLMs' help on how to secure their online accounts or protect their computers from cyber attacks. To the best of our knowledge, no prior study has collected or analyzed the S&P questions users ask LLMs; prior research on LLM response quality relied on expert-authored S&P misconceptions or FAQs rather than user queries. Drawing from WildChat, a dataset of 3.2M user-LLM conversations collected in the wild, our study identifies 14,727 S&P prompts and categorizes them into nine categories covering a wide range of S&P topics. From the S&P prompts, we sampled 450 and performed a thematic analysis to characterize the S&P questions users ask LLMs. Separate from the thematic analysis, we curated 270 advice-seeking S&P prompts, where users ask for recommendations, guidance, or specific S&P information. We measured LLM response quality and consistency when posing the prompt to LLMs 10 times. We found that commercial LLMs outperform open-weight models (GPT 5.5 provided "good enough" responses on 98% of prompts; Llama 4 on 47%). However, among prompts that received high-quality responses on average, commercial models sometimes produce contradictory responses across runs, risking confusing or misleading users.
Existing safety evaluations for large language models overlook whether responses preserve comparable medical information across different user phrasings of the same question. To address this, we introduce the Medical Information Response Audit (MIRA), a bilingual, controlled benchmark that assesses whether LLMs provide comparable medical information across user-side language, register, and health literacy signals. MIRA contains 4,320 prompts built from 60 medically reviewed, low-risk health questions. Across five mainstream LLMs, models answered all medical questions, but responses to low health-literacy signals consistently omitted more key information, provided fewer concrete next steps, and offered less support for independent judgment. We term this pattern Differential Information Dilution (DID). A comparison with 300 real-world health queries provides preliminary evidence of rank-order validity. A knowledge-guided mitigation prompt reduces information dilution for most models, with the largest reductions in underinformative simplification observed for Claude (~8%) and Qwen (~6%). Code and data are available at https://github.com/Rainxu09/MIRA.
In this paper, we discuss question-answer dataset for LLM safety evaluation, with a focus on illegal activities. Specifically, on the basis of manual analysis of AnswerCarefully, we introduce several additional information, methods for creating question-answer examples, and a rubric for evaluating LLM-generated responses. The outcomes of this study are intended to be shared with the "JAI-Trust" project.