Vision-Language Models (VLMs) expand the attack surface of safety-aligned systems by coupling visual perception with text generation. Existing multimodal jailbreak attacks primarily rely on crafted visual content, adversarial perturbations, or image-specific attack strategies, leaving the potential of reusable visual anchors in benign natural images largely unexplored. To address the problem, we introduce \textbf{MemJack}, a memory-augmented multi-agent framework for automated VLM red-teaming with natural images. MemJack combines visual-anchor discovery, visual-semantic camouflage, response evaluation, reflection-guided repair, and dynamic replanning within a closed-loop attack pipeline. Beyond attack generation, MemJack automatically transforms public images into attack anchors, enables the construction of \textbf{MemJack-Bench}, a dataset of over 113,000 interactive multimodal jailbreak trajectories for safety evaluation and defensive alignment. Extensive empirical evaluations across full, unmodified COCO val2017 images demonstrate that MemJack achieves a 71.48\% attack success rate (ASR) against Qwen3-VL-Plus, scaling to 90\% under extended budgets. Compared with representative multimodal jailbreak baselines under the same natural-image evaluation setting, MemJack achieves the highest ASR while requiring fewer mean rounds to success, demonstrating superior jailbreak effectiveness on VLMs. These results demonstrate that benign natural images can act as transferable jailbreak anchors and reveal substantial vulnerabilities in current safety-aligned VLMs.

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