Multimodal large language models (MLLMs) are increasingly deployed in real-world systems, yet their safety under adversarial prompting remains underexplored. We present a two-phase evaluation of MLLM harmlessness using a fixed benchmark of 726 adversarial prompts authored by 26 professional red teamers. Phase 1 assessed GPT-4o, Claude Sonnet 3.5, Pixtral 12B, and Qwen VL Plus; Phase 2 evaluated their successors (GPT-5, Claude Sonnet 4.5, Pixtral Large, and Qwen Omni) yielding 82,256 human harm ratings. Large, persistent differences emerged across model families: Pixtral models were consistently the most vulnerable, whereas Claude models appeared safest due to high refusal rates. Attack success rates (ASR) showed clear alignment drift: GPT and Claude models exhibited increased ASR across generations, while Pixtral and Qwen showed modest decreases. Modality effects also shifted over time: text-only prompts were more effective in Phase 1, whereas Phase 2 produced model-specific patterns, with GPT-5 and Claude 4.5 showing near-equivalent vulnerability across modalities. These findings demonstrate that MLLM harmlessness is neither uniform nor stable across updates, underscoring the need for longitudinal, multimodal benchmarks to track evolving safety behaviour.