# ICO: Enhancing Semantic-Shift Jailbreaks via Iterative Context Optimization

arXiv: https://arxiv.org/abs/2608.03210 · HTML: https://mlsanity.com/paper/2608.03210/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Jailbreaking, one of 12 directions in LLM safety and security.
- Builds on 28 of its 34 references that are in the map.
- First posted on arXiv 4 Aug 2026.

## Placed in

- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)

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

- [Language Models are Few-Shot Learners](https://mlsanity.com/paper/2005.14165/) (2020)
- [GPT-4 Technical Report](https://mlsanity.com/paper/2303.08774/) (2023)
- [The Llama 3 Herd of Models](https://mlsanity.com/paper/2407.21783/) (2024)
- [Visual Instruction Tuning](https://mlsanity.com/paper/2304.08485/) (2023)
- [BLIP-2: Bootstrapping Language-Image Pre-training with Frozen Image Encoders and Large Language Models](https://mlsanity.com/paper/2301.12597/) (2023)
- [Flamingo: a Visual Language Model for Few-Shot Learning](https://mlsanity.com/paper/2204.14198/) (2022)
- [On the Opportunities and Risks of Foundation Models](https://mlsanity.com/paper/2108.07258/) (2021)
- [Gemini 1.5: Unlocking multimodal understanding across millions of tokens of context](https://mlsanity.com/paper/2403.05530/) (2024)
- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (2023)
- [Qwen3-VL Technical Report](https://mlsanity.com/paper/2511.21631/) (2025)
- [Jailbroken: How Does LLM Safety Training Fail?](https://mlsanity.com/paper/2307.02483/) (2023)
- [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)
- [Red Teaming Language Models with Language Models](https://mlsanity.com/paper/2202.03286/) (2022)
- [DeepSeek-V3.2: Pushing the Frontier of Open Large Language Models](https://mlsanity.com/paper/2512.02556/) (2025)
- [Red Teaming Language Models to Reduce Harms: Methods, Scaling Behaviors, and Lessons Learned](https://mlsanity.com/paper/2209.07858/) (2022)
- [Tree of Attacks: Jailbreaking Black-Box LLMs Automatically](https://mlsanity.com/paper/2312.02119/) (2023)
- [Jailbreaking ChatGPT via Prompt Engineering: An Empirical Study](https://mlsanity.com/paper/2305.13860/) (2023)
- [FigStep: Jailbreaking Large Vision-Language Models via Typographic Visual Prompts](https://mlsanity.com/paper/2311.05608/) (2023)
- [A StrongREJECT for Empty Jailbreaks](https://mlsanity.com/paper/2402.10260/) (2024)
- [Toxicity in ChatGPT: Analyzing Persona-assigned Language Models](https://mlsanity.com/paper/2304.05335/) (2023)
- [Visual Adversarial Examples Jailbreak Aligned Large Language Models](https://mlsanity.com/paper/2306.13213/) (2023)
- [MM-SafetyBench: A Benchmark for Safety Evaluation of Multimodal Large Language Models](https://mlsanity.com/paper/2311.17600/) (2023)
- [AutoDAN-Turbo: A Lifelong Agent for Strategy Self-Exploration to Jailbreak LLMs](https://mlsanity.com/paper/2410.05295/) (2024)
- [Images are Achilles' Heel of Alignment: Exploiting Visual Vulnerabilities for Jailbreaking Multimodal Large Language Models](https://mlsanity.com/paper/2403.09792/) (2024)
- [FlipAttack: Jailbreak LLMs via Flipping](https://mlsanity.com/paper/2410.02832/) (2024)
- [In-Context Representation Hijacking](https://mlsanity.com/paper/2512.03771/) (2025)
- [Jailbreaking Vision-Language Models Through the Visual Modality](https://mlsanity.com/paper/2605.00583/) (2026)

## Abstract (arXiv)

Foundation models have achieved remarkable success across diverse tasks, but they remain vulnerable. To investigate such vulnerabilities, semantic-shift jailbreaks have recently emerged as a promising attack paradigm. They bypass explicit safety mechanisms by replacing harmful terms in original harmful questions with benign alternatives and leveraging contextual information to induce the target model to reinterpret these alternatives as their corresponding harmful concepts. However, existing semantic-shift jailbreaks often achieve limited effectiveness. In this work, we reveal that this limitation arises from overlooking the semantic-shift capability of contexts. Through systematic analysis, we find that contexts exhibit substantially different abilities in inducing semantic shifts: contexts with stronger semantic-shift capabilities are more likely to guide models toward recovering harmful meanings and achieving successful jailbreaks. Based on this finding, we systematically identify and distill the characteristics of effective contexts and propose a black-box context-aware semantic-shift jailbreak framework with Iterative Context Optimization (ICO). In each iteration, ICO leverages these characteristics and feedback from the target model to optimize contexts. Extensive experiments on three datasets and eight target foundation models demonstrate that ICO consistently outperforms eight state-of-the-art baselines, achieving an average attack success rate of 74.6%.