Rethinking LLM Jailbreak Evaluation: Continuous Risk Landscapes Beyond Binary Outcomes

A binary success indicator is a natural representation for discriminative tasks such as image classification under adversarial perturbations, where each input is mapped to a single prediction. However, generative tasks are fundamentally different: an LLM jailbreak prompt induces a distribution over open-ended trajectories, while a sampled response reveals only one path. Yet LLM jailbreak evaluation typically retains the binary response indicator underlying attack success rate, obscuring the surrounding structure of possible generations. We introduce a continuous, context-conditioned risk landscape over first-token branches, estimated by fixing candidate openings and repeatedly sampling their continuations. This continuous risk-landscape perspective reveals two complementary properties: current decoder exposure and safe rerouting capacity, which have been obscured by binary-indicator-based ASR. The resulting representation also provides a common basis for comparing clean prompts, attacked variants, and attack strength against a known adaptive defense. Across multiple target models and jailbreak attacks, we uncover risky branches beneath apparently safe outputs, identify qualitatively different ways attacks reshape the model's opening distribution, and show that attacks strongest before a defense do not necessarily remain the strongest after the defense reacts. These findings recast jailbreaks as deformations of the surrounding continuation-risk landscape, establishing a more informative foundation for understanding jailbreak behavior and developing safer language models.