# ASCII Attack: Recontextualising Harmful Requests as Artistic Critique in Large Language Models

arXiv: https://arxiv.org/abs/2609.02215 · HTML: https://mlsanity.com/paper/2609.02215/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Safety alignment and jailbreak attacks, one of 10 directions in LLM alignment / RLHF / preference optimisation.
- Builds on 28 of its 48 references that are in the map.
- First posted on arXiv 2 Sep 2026.

## Placed in

- LLM alignment / RLHF / preference optimisation / [Safety alignment and jailbreak attacks](https://mlsanity.com/alignment/safety-alignment-and-jailbreak-attacks/)
- LLM safety and security / [Safety alignment, refusal and guardrails](https://mlsanity.com/safety/safety-alignment-refusal-and-guardrails/)

## Builds on (most cited first, 28 of 28)

- [Attention Is All You Need](https://mlsanity.com/paper/1706.03762/) (2017)
- [The Llama 3 Herd of Models](https://mlsanity.com/paper/2407.21783/) (2024)
- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (2023)
- [Gemma 3 Technical Report](https://mlsanity.com/paper/2503.19786/) (2025)
- [HarmBench: A Standardized Evaluation Framework for Automated Red Teaming and Robust Refusal](https://mlsanity.com/paper/2402.04249/) (2024)
- [Jailbreaking Black Box Large Language Models in Twenty Queries](https://mlsanity.com/paper/2310.08419/) (2023)
- [Llama Guard: LLM-based Input-Output Safeguard for Human-AI Conversations](https://mlsanity.com/paper/2312.06674/) (2023)
- [Refusal in Language Models Is Mediated by a Single Direction](https://mlsanity.com/paper/2406.11717/) (2024)
- [Tree of Attacks: Jailbreaking Black-Box LLMs Automatically](https://mlsanity.com/paper/2312.02119/) (2023)
- [WildGuard: Open One-Stop Moderation Tools for Safety Risks, Jailbreaks, and Refusals of LLMs](https://mlsanity.com/paper/2406.18495/) (2024)
- ["Do Anything Now": Characterizing and Evaluating In-The-Wild Jailbreak Prompts on Large Language Models](https://mlsanity.com/paper/2308.03825/) (2023)
- [Catastrophic Jailbreak of Open-source LLMs via Exploiting Generation](https://mlsanity.com/paper/2310.06987/) (2023)
- [GPT-4 Is Too Smart To Be Safe: Stealthy Chat with LLMs via Cipher](https://mlsanity.com/paper/2308.06463/) (2023)
- [FigStep: Jailbreaking Large Vision-Language Models via Typographic Visual Prompts](https://mlsanity.com/paper/2311.05608/) (2023)
- [DeepInception: Hypnotize Large Language Model to Be Jailbreaker](https://mlsanity.com/paper/2311.03191/) (2023)
- [Are aligned neural networks adversarially aligned?](https://mlsanity.com/paper/2306.15447/) (2023)
- [Low-Resource Languages Jailbreak GPT-4](https://mlsanity.com/paper/2310.02446/) (2023)
- [ArtPrompt: ASCII Art-based Jailbreak Attacks against Aligned LLMs](https://mlsanity.com/paper/2402.11753/) (2024)
- [The Hidden Risks of Large Reasoning Models: A Safety Assessment of R1](https://mlsanity.com/paper/2502.12659/) (2025)
- [CodeAttack: Revealing Safety Generalization Challenges of Large Language Models via Code Completion](https://mlsanity.com/paper/2403.07865/) (2024)
- [EasyJailbreak: A Unified Framework for Jailbreaking Large Language Models](https://mlsanity.com/paper/2403.12171/) (2024)
- [garak: A Framework for Security Probing Large Language Models](https://mlsanity.com/paper/2406.11036/) (2024)
- [AILuminate: Introducing v1.0 of the AI Risk and Reliability Benchmark from MLCommons](https://mlsanity.com/paper/2503.05731/) (2025)
- [PyRIT: A Framework for Security Risk Identification and Red Teaming in Generative AI System](https://mlsanity.com/paper/2410.02828/) (2024)
- [Multi-Turn Jailbreaks Are Simpler Than They Seem](https://mlsanity.com/paper/2508.07646/) (2025)
- [HarmMetric Eval: Benchmarking Metrics and Judges for LLM Harmfulness Assessment](https://mlsanity.com/paper/2509.24384/) (2025)
- [Adversarial Poetry as a Universal Single-Turn Jailbreak Mechanism in Large Language Models](https://mlsanity.com/paper/2511.15304/) (2025)
- [ArtPerception: ASCII Art-based Jailbreak on LLMs with Recognition Pre-test](https://mlsanity.com/paper/2510.10281/) (2025)

## Abstract (arXiv)

Safety alignment trains large language models to refuse harmful requests stated plainly, but that training is applied mostly to surface form. Requests that only recontextualise the same operational content, changing how the model reads it, are therefore only weakly covered. The ASCII Attack is one such recontextualisation. It is single-turn and black-box: one message, with no access to model internals. It embeds a fully legible harmful request in ASCIl-art characters, presents it as artwork, and asks for feedback. Unlike ArtPrompt, it hides nothing: the request stays readable. The reply is written as artistic critique and can contain operational detail that a plain request would have been refused for. Every framed prompt is paired with a direct-question control, so the contrast is isolated from topic, model and decoding variation. The contrast identifies a bundled surface, not one isolated channel. Across eleven models and eight harm topics, a harm-aware classifier judges 62% of framed prompts harmful against 42% of controls. On the most susceptible model the framed prompt succeeds 93% of the time. A single query matches or exceeds published single-query attacks under four of five harm judges. The effect tracks the model more than the topic and does not diminish with scale. At least one judge dissents from the panel majority on nearly two-thirds of framed rows, which is itself a measurement-validity finding. That pattern is consistent with mismatched generalisation.