Multimodal Large Language Models (MLLMs) are vulnerable to jailbreak attacks, which can elicit harmful responses from MLLMs. Many MLLMs support multi-image inputs, inadvertently introducing new vulnerabilities due to less efforts on multi-image safety alignment. Previous MLLM jailbreak methods only uses a single image, which restricts the attack space: they cannot distribute harmful requests across multiple images, carry abundant information, or exploit additional visual reasoning tasks to distract MLLMs. To address these limitations, in this paper, we propose a compositional jailbreak framework, DMN, which leverages Distributed instruction, Multimodal evidence and a Number chain task to fully enhance the jailbreak performance. Extensive experiments show that DMN is highly effective for MLLM jailbreaking, e.g. achieving attack success rates of over 90% on GPT-4o, Gemini-2.5-pro and Claude Sonnet 4, surpassing other baselines by a large margin. This compositional, multi-image jailbreak strategy reveals fundamental weaknesses in their safety mechanisms.

Multi-turn jailbreak attacks simulate real-world human interactions by engaging large language models (LLMs) in iterative dialogues, exposing critical safety vulnerabilities. However, existing methods often struggle to balance semantic coherence with attack effectiveness, resulting in either benign semantic drift or ineffective detection evasion. To address this challenge, we propose Reasoning-Augmented Conversation (RACE), a novel multi-turn jailbreak framework that reformulates harmful queries into benign reasoning tasks and leverages LLMs’ strong reasoning capabilities to compromise safety alignment. Specifically, we introduce an attack state machine framework to systematically model problem translation and iterative reasoning, ensuring coherent query generation across multiple turns. Building on this framework, we design gain-guided exploration, self-play, and rejection feedback modules to preserve attack semantics, enhance effectiveness, and sustain reasoning-driven attack progression. Extensive experiments on multiple LLMs demonstrate that RACE achieves state-of-the-art attack effectiveness in complex conversational scenarios, with attack success rates (ASRs) increasing by up to 96%. Notably, our approach achieves average ASR of 83.3% against leading commercial models, including Gemini 2.0 Flashing Thinking and OpenAI o1, underscoring its potency.