# When Search Goes Wrong: Red-Teaming Web-Augmented Large Language Models

arXiv: https://arxiv.org/abs/2510.09689 · HTML: https://mlsanity.com/paper/2510.09689/

## Key facts

- Cited by 1 papers in the map (data through 14 Oct 2026).
- Placed in Prompt injection and agent security, one of 12 directions in LLM safety and security.
- Builds on 28 of its 42 references that are in the map.
- First posted on arXiv 9 Oct 2025.

## Placed in

- LLM safety and security / [Prompt injection and agent security](https://mlsanity.com/safety/prompt-injection-and-agent-security/)

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

- [The Llama 3 Herd of Models](https://mlsanity.com/paper/2407.21783/) (2024)
- [Chain-of-Thought Prompting Elicits Reasoning in Large Language Models](https://mlsanity.com/paper/2201.11903/) (2022)
- [Retrieval-Augmented Generation for Knowledge-Intensive NLP Tasks](https://mlsanity.com/paper/2005.11401/) (2020)
- [Evaluating Large Language Models Trained on Code](https://mlsanity.com/paper/2107.03374/) (2021)
- [Gemini 2.5: Pushing the Frontier with Advanced Reasoning, Multimodality, Long Context, and Next Generation Agentic Capabilities](https://mlsanity.com/paper/2507.06261/) (2025)
- [Universal and Transferable Adversarial Attacks on Aligned Language Models](https://mlsanity.com/paper/2307.15043/) (2023)
- [Survey of Hallucination in Natural Language Generation](https://mlsanity.com/paper/2202.03629/) (2022)
- [WebGPT: Browser-assisted question-answering with human feedback](https://mlsanity.com/paper/2112.09332/) (2021)
- [HarmBench: A Standardized Evaluation Framework for Automated Red Teaming and Robust Refusal](https://mlsanity.com/paper/2402.04249/) (2024)
- [Llama Guard: LLM-based Input-Output Safeguard for Human-AI Conversations](https://mlsanity.com/paper/2312.06674/) (2023)
- [Red Teaming Language Models with Language Models](https://mlsanity.com/paper/2202.03286/) (2022)
- [Red Teaming Language Models to Reduce Harms: Methods, Scaling Behaviors, and Lessons Learned](https://mlsanity.com/paper/2209.07858/) (2022)
- [Texygen: A Benchmarking Platform for Text Generation Models](https://mlsanity.com/paper/1802.01886/) (2018)
- [Certifying LLM Safety against Adversarial Prompting](https://mlsanity.com/paper/2309.02705/) (2023)
- [Jailbreak Attacks and Defenses Against Large Language Models: A Survey](https://mlsanity.com/paper/2407.04295/) (2024)
- [Red-Teaming Large Language Models using Chain of Utterances for Safety-Alignment](https://mlsanity.com/paper/2308.09662/) (2023)
- [How Abilities in Large Language Models are Affected by Supervised Fine-tuning Data Composition](https://mlsanity.com/paper/2310.05492/) (2023)
- [On Second Thought, Let's Not Think Step by Step! Bias and Toxicity in Zero-Shot Reasoning](https://mlsanity.com/paper/2212.08061/) (2022)
- [LLM Lies: Hallucinations are not Bugs, but Features as Adversarial Examples](https://mlsanity.com/paper/2310.01469/) (2023)
- [MART: Improving LLM Safety with Multi-round Automatic Red-Teaming](https://mlsanity.com/paper/2311.07689/) (2023)
- [ProPILE: Probing Privacy Leakage in Large Language Models](https://mlsanity.com/paper/2307.01881/) (2023)
- [Red-Teaming for Generative AI: Silver Bullet or Security Theater?](https://mlsanity.com/paper/2401.15897/) (2024)
- [A Safe Harbor for AI Evaluation and Red Teaming](https://mlsanity.com/paper/2403.04893/) (2024)
- [ART: Automatic Red-teaming for Text-to-Image Models to Protect Benign Users](https://mlsanity.com/paper/2405.19360/) (2024)
- [Llama Guard 3-1B-INT4: Compact and Efficient Safeguard for Human-AI Conversations](https://mlsanity.com/paper/2411.17713/) (2024)
- [RAG LLMs are Not Safer: A Safety Analysis of Retrieval-Augmented Generation for Large Language Models](https://mlsanity.com/paper/2504.18041/) (2025)
- [Unsafe LLM-Based Search: Quantitative Analysis and Mitigation of Safety Risks in AI Web Search](https://mlsanity.com/paper/2502.04951/) (2025)
- [Boosting Big Brother: Attacking Search Engines with Encodings](https://mlsanity.com/paper/2304.14031/) (2023)

## Built on by (most cited first, 1 of 1)

- [Breadcrumbing Search Agents](https://mlsanity.com/paper/2608.04565/) (2026)

## Abstract (arXiv)

Large Language Models (LLMs) have been augmented with web search to overcome the limitations of the static knowledge boundary by accessing up-to-date information from the open Internet. While this integration enhances model capability, it also introduces a distinct safety threat surface: the retrieval and citation process has the potential risk of exposing users to harmful or low-credibility web content. Existing red-teaming methods are largely designed for standalone LLMs as they primarily focus on unsafe generation, ignoring risks emerging from the complex search workflow. To address this gap, we propose CREST-Search, a pioneering red-teaming framework for LLMs with web search. The cornerstone of CREST-Search is three novel attack strategies that generate seemingly benign search queries yet induce unsafe citations. It also employs an iterative in-context refinement mechanism to strengthen adversarial effectiveness under black-box constraints. In addition, we construct a search-specific harmful dataset, WebSearch-Harm, which enables fine-tuning a specialized red-teaming model to improve query quality. Our experiments demonstrate that CREST-Search can effectively bypass safety filters and systematically expose vulnerabilities in web search-based LLM systems, underscoring the necessity of the development of robust search models.