As large Vision-Language Models (VLMs) gain prominence, ensuring their safe deployment has become critical. Recent studies have explored VLM robustness against jailbreak attacks—techniques that exploit model vulnerabilities to elicit harmful outputs. However, the limited availability of diverse multimodal data has constrained current approaches to rely heavily on adversarial or manually crafted images derived from harmful text datasets, which often lack effectiveness and diversity across different contexts. In this paper, we propose IDEATOR, a novel jailbreak method that autonomously generates malicious image-text pairs for black-box jailbreak attacks. IDEATOR is grounded in the insight that VLMs themselves could serve as powerful red team models for generating multimodal jailbreak prompts. Specifically, IDEATOR leverages a VLM to create targeted jailbreak texts and pairs them with jailbreak images generated by a state-of-the-art diffusion model. Extensive experiments demonstrate IDEATOR’s high effectiveness and transferability, achieving a 94% attack success rate (ASR) in jailbreaking MiniGPT-4 with an average of only 5.34 queries, and high ASRs of 82%, 88%, and 75% when transferred to LLaVA, InstructBLIP, and Chameleon, respectively. Building on IDEATOR’s strong transferability and automated process, we introduce the VLBreakBench, a safety benchmark comprising 3,654 multimodal jailbreak samples. Our benchmark results on 11 recently released VLMs reveal significant gaps in safety alignment. For instance, our challenge set achieves ASRs of 46.31% on GPT-4o and 19.65% on Claude-3.5-Sonnet, underscoring the urgent need for stronger defenses.