As large language models (LLMs) are increasingly deployed as general-purpose conversational assistants, they must handle diverse user requests while reliably refusing harmful ones. Jailbreak attacks craft adversarial instructions or conversational contexts to elicit unsafe responses despite these safeguards. However, existing jailbreak benchmarks often rely on manually designed or collected prompts, making it difficult to systematically extend coverage to new threat conditions. Moreover, existing attack search methods typically optimize for attack success rate (ASR), providing limited insight into how model behavior changes locally between safe refusal and unsafe response. To address these limitations, we present JailBound, a unified jailbreak evaluation framework that combines automated benchmark construction with first-order loss (FOL)-guided dual-branch search. JailBound organizes threats by risk category, application domain, and attack type. Conditioned on this taxonomy, a fine-tuned meta-attack generator synthesizes evaluation prompts across diverse threat conditions. FOL serves as a local sensitivity signal for exploring high-value attack states and behavior-sensitive states. We evaluate JailBound across 46 LLMs from 13 model families under a unified experimental protocol. Under matched settings, the High-Value Branch improves average ASR over a ZOL-only baseline by 5.1 and 4.9 percentage points across the two evaluation settings. Under local perturbations, states from the Safety-Sensitivity Branch exhibit higher behavioral flip rates than those from the High-Value Branch across all tested radii for JailBound and S-Eval, indicating greater local sensitivity of judge-assigned safety labels. Warning: this paper includes examples that may be offensive or harmful.

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