Refusing Everything Looks Safe: Restoring the Benign Arm to Encoded-Prompt Evaluation

Safety classifiers ("guards") are the dominant black-box defense for vision-language models, yet a guard judges an input's surface form, not its meaning: a harmful request re-encoded as set theory, formal logic, a classical language, code, or text rendered inside an image slips past a guard that would block it in plain language - the decode gap. The standard fix is a preprocessor that recovers image content and decodes the encoding before the guard. We build one and evaluate it against an ensemble of eleven published encoding attacks, counting a behavior as broken if any attack succeeds. That metric separates two mechanisms such defenses conflate. Restoring a view the guard never had improves it on both axes at once: it blocks far more attacks, and, measured on a category-balanced benign set, it blocks fewer benign requests, because restating a request normalizes the borderline phrasing a classifier over-flags. It still does not make the system safer: against an attacker free to choose among eleven encodings, closing one channel relocates the success rather than removing it, and no ensemble contrast survives multiple-comparison correction. What does lower ensemble attack success is re-screening the recovered pre-decode surface, and that step is where the entire benign cost falls. The safety-utility trade-off is therefore not a property of recovery; it is localized to one step. Across the full guard x target x condition factorial, no configuration reaches an ensemble attack-success rate at or below 40% while holding benign over-refusal under 70%. The per-attack averages usually reported understate the attacker roughly fourfold, which is why this frontier is easy to miss. Composing across defense families is the one lever that moved the safety axis, beating every configuration we measured, and still landing far outside any deployable refusal budget.

Large language models (LLMs) are becoming increasingly integrated into mainstream development platforms and daily technological workflows, typically behind moderation and safety controls. Despite these controls, preventing prompt-based policy evasion remains challenging, and adversaries continue to "jailbreak" LLMs by crafting prompts that circumvent implemented safety mechanisms. Prior work has established cipher-mediated interaction, code-embedded decryption, prompt decomposition and reconstruction, and layered custom encryption as viable attack primitives. However, reported evaluations generally collapse visible acceptance, successful recovery of the concealed request, and subsequent execution into an aggregate attack-success outcome. This leaves limited evidence about where multistage prompt-transformation attacks fail within an observable black-box interaction. This paper introduces RoguePrompt, a jailbreak pipeline that partitions a forbidden prompt and applies two nested encodings, Vigenere followed by ROT13, along with natural-language reconstruction instructions. RoguePrompt was developed and evaluated under a black-box threat model, with only API or user-interface access to the hosted models, and was tested on 313 real-world, hard-rejected prompts. Success was measured in terms of moderation bypass, instruction reconstruction, and execution when the relevant stage exceeded its automated criterion. RoguePrompt achieved average rates of 93.93% for filter bypass, 79.02% for reconstruction, and 70.18% for execution. These results demonstrate the effectiveness of layered prompt encoding while providing stage-level evidence of where multistage jailbreaks fail during moderation bypass, instruction reconstruction, and execution.

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.