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This research introduces 3R-Bench, a critical benchmark revealing how conversational history drastically alters Large Language Models' willingness to assist with cybersecurity tasks. The study demonstrates that prior refusals or accepted interactions significantly shift compliance rates, highlighting a major gap in current safety evaluation methods that ignores dialogue context. For the AI community, this underscores the urgent need for robust mechanisms that distinguish between malicious actors and legitimate defenders without relying solely on static request analysis.
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Same Request, Different Boundary: Evaluating Cybersecurity Assistance across Conversational Contexts

arXiv2 min read

arXiv:2609.00578v1 Announce Type: new Abstract: 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.

Abstract: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.

Artificial Intelligence (cs.AI); Cryptography and Security (cs.CR)

arXiv:2609.00578 [cs.AI]

(or arXiv:2609.00578v1 [cs.AI] for this version)

https://doi.org/10.48550/arXiv.2609.00578 Focus to learn more arXiv-issued DOI via DataCite (pending registration)

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Full text under the publisher's open licence · 263 words

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