Security and Privacy Prompts in the Wild: What Users Ask LLMs and How LLMs Respond
Authors: Hobin Kim, Xiaoyuan Wu, Omer Akgul, Lujo Bauer, Nicolas Christin
Organizations: Carnegie Mellon University · RSAC Labs
Abstract
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.
Large Language Models (LLMs) can solve complex problems, but their misuse in high-risk domains can lead to severe consequences. Model providers therefore restrict assistance for potentially harmful requests. Refusing all cybersecurity requests would therefore harm legitimate users. Providers need a mechanism to block malicious use without denying legitimate assistance to defenders. Existing cybersecurity-specific datasets evaluate this mechanism, but none considers the conversational context of a request. We introduce 3R-Bench (Refusal, Repetition, and Revision), a benchmark of 150 real-world cybersecurity requests augmented with two adversarial conversational settings, and evaluate eight LLMs on it. Prior assistant behavior strongly changes responses to an unchanged request: among 376 available pairs from a 400-pair panel, compliance rises from 62.0% after refused history to 85.1% after accepted history. The opposite pattern appears under dialogue decomposition. In comparison, compliance falls from 501/800 direct responses to 172/800 after dialogue; among 738 pairs returning model-authored text in both conditions, the decrease is 45.1 points. Failure feedback recovers only a small fraction of this loss.
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.
Tanise Ceron, Joachim Baumann, Elisa Bassignana +3
Large language models (LLMs) are rapidly being adopted for tasks like drafting emails, summarizing meetings, and answering health questions. In these settings, users may need to share private information (e.g., contact details, health records). To evaluate LLMs' ability to identify and redact such information, prior work introduced real-life, scenario-based benchmarks (e.g., ConfAIde, PrivacyLens) and found that LLMs can leak private information in complex scenarios. However, these evaluations relied on proxy LLMs to judge the helpfulness and privacy-preservation quality of LLM responses, rather than directly measuring users' perceptions. To understand how users perceive the helpfulness and privacy-preservation quality of LLM responses to privacy-sensitive scenarios, we conducted a user study (n=94) using 90 PrivacyLens scenarios. We found that users had low agreement with each other when evaluating identical LLM responses. In contrast, five proxy LLMs reached high agreement, yet each proxy LLM had low correlation with users' evaluations. These results indicate that proxy LLMs cannot accurately estimate users' wide range of perceptions of utility and privacy in privacy-sensitive scenarios. We discuss the need for more user-centered studies to measure LLMs' ability to help users while preserving privacy, and for improving alignment between LLMs and users in estimating perceived privacy and utility.