Recent research has focused on exploring the vulnerabilities of Large Language Models (LLMs), aiming to elicit harmful and/or sensitive content from LLMs. However, due to the insufficient research on dual-jailbreaking -- attacks targeting both LLMs and Guardrails, the effectiveness of existing attacks is limited when attempting to bypass safety-aligned LLMs shielded by guardrails. Therefore, in this paper, we propose DualBreach, a target-driven framework for dual-jailbreaking. DualBreach employs a Target-driven Initialization (TDI) strategy to dynamically construct initial prompts, combined with a Multi-Target Optimization (MTO) method that utilizes approximate gradients to jointly adapt the prompts across guardrails and LLMs, which can simultaneously save the number of queries and achieve a high dual-jailbreaking success rate. For black-box guardrails, DualBreach either employs a powerful open-sourced guardrail or imitates the target black-box guardrail by training a proxy model, to incorporate guardrails into the MTO process.
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