We introduce Siege, a multi-turn adversarial framework that models the gradual erosion of Large Language Model (LLM) safety through a tree search perspective. Unlike single-turn jailbreaks that rely on one meticulously engineered prompt, Siege expands the conversation at each turn in a breadth-first fashion, branching out multiple adversarial prompts that exploit partial compliance from previous responses. By tracking these incremental policy leaks and re-injecting them into subsequent queries, Siege reveals how minor concessions can accumulate into fully disallowed outputs. Evaluations on the JailbreakBench dataset show that Siege achieves a 100% success rate on GPT-3.5-turbo and 97% on GPT-4 in a single multi-turn run, using fewer queries than baselines such as Crescendo or GOAT. This tree search methodology offers an in-depth view of how model safeguards degrade over successive dialogue turns, underscoring the urgency of robust multi-turn testing procedures for language models.
View on arXiv@article{zhou2025_2503.10619,
title={ Siege: Autonomous Multi-Turn Jailbreaking of Large Language Models with Tree Search },
author={ Andy Zhou },
journal={arXiv preprint arXiv:2503.10619},
year={ 2025 }
}