Sanket Mendapara

Typographic prompt injection exploits vision language models' (VLMs) ability to read text rendered in images, posing a growing threat as VLMs power autonomous agents. Prior work typically focus on maximizing attack success rate (ASR) but does not explain \emph{why} certain renderings bypass safety alignment. We make two contributions. First, an empirical study across four VLMs including GPT-4o and Claude, twelve font sizes, and ten transformations reveals that multimodal embedding distance strongly predicts ASR ($r{=}{-}0.71$ to ${-}0.93$, $p{<}0.01$), providing an interpretable, model agnostic proxy. Since embedding distance predicts ASR, reducing it should improve attack success, but the relationship is mediated by two factors: perceptual readability (whether the VLM can parse the text) and safety alignment (whether it refuses to comply). Second, we use this as a red teaming tool: we directly maximize image text embedding similarity under bounded $\ell_\infty$ perturbations via CWA-SSA across four surrogate embedding models, stress testing both factors without access to the target model. Experiments across five degradation settings on GPT-4o, Claude Sonnet 4.5, Mistral-Large-3, and Qwen3-VL confirm that optimization recovers readability and reduces safety aligned refusals as two co-occurring effects, with the dominant mechanism depending on the model's safety filter strength and the degree of visual degradation.