Exposing LLM Safety Gaps Through Mathematical Encoding:New Attacks and Systematic Analysis

Large language models (LLMs) employ safety mechanisms to prevent harmful outputs, yet these defenses primarily rely on semantic pattern matching. We show that encoding harmful prompts as coherent mathematical problems -- using formalisms such as set theory, formal logic, and quantum mechanics -- bypasses these filters at high rates, achieving 46%--56% average attack success across eight target models and two established benchmarks. Crucially, the effectiveness depends not on mathematical notation itself, but on whether a helper LLM deeply reformulates the harmful content into a genuine mathematical problem: rule-based encodings that apply mathematical formatting without such reformulation perform no better than unencoded baselines. We introduce a novel Formal Logic encoding that achieves attack success comparable to Set Theory, demonstrating that this vulnerability generalizes across mathematical formalisms. Additional experiments with repeat post-processing confirm that these attacks are robust to simple prompt augmentation. Notably, newer models (GPT-5, GPT-5-Mini) show substantially greater robustness than older models, though they remain vulnerable. Our findings highlight fundamental gaps in current safety frameworks and motivate defenses that reason about mathematical structure rather than surface-level semantics.

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16 pages, 2 figures, 4 tables. Accepted as a long paper at the 39th Canadian Conference on Artificial Intelligence (Canadian AI 2026)