The widespread practice of fine-tuning open-source Vision-Language Models (VLMs) raises a critical security concern: jailbreak vulnerabilities in base models may persist in downstream variants, enabling transferable attacks across fine-tuned systems. To investigate this risk, we propose the Simulated Ensemble Attack (SEA), a grey-box jailbreak framework that assumes full access to the base VLM but no knowledge of the fine-tuned target. SEA enhances transferability via Fine-tuning Trajectory Simulation (FTS), which models bounded parameter variations in the vision encoder, and Targeted Prompt Guidance (TPG), which stabilizes adversarial optimization through auxiliary textual guidance. Experiments on the Qwen2-VL family demonstrate that SEA achieves consistently high transfer success and toxicity rates across diverse fine-tuned variants, including safety-enhanced models, while standard PGD-based image jailbreaks exhibit negligible transferability. Further analysis reveals that fine-tuning primarily induces localized parameter shifts around the base model, explaining why attacks optimized over a simulated neighborhood transfer effectively. We also show that SEA generalizes across different base generations (e.g., Qwen2.5/3-VL), indicating that its effectiveness arises from shared fine-tuning-induced behaviors rather than architecture- or initialization-specific factors.