arXiv:2510.09689v1 Announce Type: cross Abstract: Large Language Models (LLMs) excel at tasks such as dialogue, summarization, and question answering, yet they struggle to adapt to specialized domains and evolving facts. To overcome this, web search has been integrated into LLMs, allowing real-time access to online content. However, this connection magnifies safety risks, as adversarial prompts combined with untrusted sources can cause severe vulnerabilities. We investigate red teaming for LLMs with web search and present CREST-Search, a framework that systematically exposes risks in such systems. Unlike existing methods for standalone LLMs, CREST-Search addresses the complex workflow of search-enabled models by generating adversarial queries with in-context learning and refining them through iterative feedback. We further construct WebSearch-Harm, a search-specific dataset to fine-tune LLMs into efficient red-teaming agents. Experiments show that CREST-Search effectively bypasses safety filters and reveals vulnerabilities in modern web-augmented LLMs, underscoring the need for specialized defenses to ensure trustworthy deployment.