Same Request, Different Boundary: Evaluating Cybersecurity Assistance across Conversational Contexts

Agentic scaffolds have dramatically improved LLM performance on complex, long-horizon tasks, yielding both broad benefits and amplified risks in domains like cybersecurity. Existing benchmarks for AI agents in cybersecurity focus mainly on measuring proficiency--how effectively agents can complete offensive security tasks--but neglect a critical question: when and how should agents refuse harmful requests? We present the first framework for establishing refusal boundaries in offensive security contexts. Our framework defines (1) principled criteria for when tasks should be refused, (2) categories of tasks that warrant refusal, and (3) evaluation methodology for measuring agent robustness under both benign and adversarial conditions. We apply this framework to assess how current LLM-powered agents adhere to appropriate refusal boundaries across a range of web-based offensive security scenarios, finding that 6 of 8 frontier models tested show near-zero refusal rates, with only 2 models (GPT-5.2 and GPT-5.1 Codex) demonstrating any meaningful refusal behavior.

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.

An attacker can split a malicious goal into sub-prompts that each look benign on their own and only become harmful in combination. Existing LLM safety benchmarks evaluate prompts one at a time, or across turns of a single chat, and so do not look for a malicious signal spread across separate sessions with no shared context. We build FragBench, a benchmark drawn from 24 real-world cyber-incident campaigns, which keeps the full attack trail: the multi-fragment kill chain, the per-fragment safety-judge verdicts, sandboxed execution traces, and a matched set of benign cover sessions. FragBench splits this trail into two paired tasks: an adversarial rewriter that hardens fragments against a single-turn safety judge (FragBench Attack), and a graph-based user-level detector trained on the resulting interactions (FragBench Defense). The single-turn judge is near chance on the released corpus by construction, but four GNN variants and three classical-ML baselines all recover the cross-session feature, reaching aggregate event-level F1 = 0.88-0.96. Defending against fragmented LLM misuse therefore requires modeling the cross-session interaction graph, rather than isolated prompts. Our generator, rewriter, sandbox harness, and detector are released at https://github.com/LidaSafety/fragbench.