Oversensitivity occurs when language models defensively reject prompts that are actually benign. This behavior not only disrupts user interactions but also obscures the boundary between harmful and harmless content. Existing benchmarks rely on static datasets that degrade over time as models evolve, leading to data contamination and diminished evaluative power. To address this, we develop a framework that dynamically generates model-specific challenging datasets, capturing emerging defensive patterns and aligning with each model’s unique behavior. Building on this approach, we construct OverBench, a benchmark that aggregates these datasets across diverse LLM families, encompassing 450,000 samples from 25 models. OverBench provides a dynamic and evolving perspective on oversensitivity, allowing for continuous monitoring of defensive triggers as models advance, highlighting vulnerabilities that static datasets overlook.