MetaBreak: Jailbreaking Online LLM Services via Special Token Manipulation
Authors: Wentian Zhu, Zhen Xiang, Wei Niu, Le Guan
Organizations: University of Georgia
Abstract
Unlike regular tokens derived from existing text corpora, special tokens are artificially created to annotate structured conversations during the fine-tuning process of Large Language Models (LLMs). Serving as metadata of training data, these tokens play a crucial role in instructing LLMs to generate coherent and context-aware responses. We demonstrate that special tokens can be exploited to construct four attack primitives, with which malicious users can reliably bypass the internal safety alignment of online LLM services and circumvent state-of-the-art (SOTA) external content moderation systems simultaneously. Moreover, we found that addressing this threat is challenging, as aggressive defense mechanisms-such as input sanitization by removing special tokens entirely, as suggested in academia-are less effective than anticipated. This is because such defense can be evaded when the special tokens are replaced by regular ones with high semantic similarity within the tokenizer's embedding space. We systemically evaluated our method, named MetaBreak, on both lab environment and commercial LLM platforms. Our approach achieves jailbreak rates comparable to SOTA prompt-engineering-based solutions when no content moderation is deployed. However, when there is content moderation, MetaBreak outperforms SOTA solutions PAP and GPTFuzzer by 11.6% and 34.8%, respectively. Finally, since MetaBreak employs a fundamentally different strategy from prompt engineering, the two approaches can work synergistically. Notably, empowering MetaBreak on PAP and GPTFuzzer boosts jailbreak rates by 24.3% and 20.2%, respectively.
Jailbreak attacks remain a critical threat to the safe deployment of large language models (LLMs). While prior work has primarily studied attacks and defenses at the prompt level, we show that this prompt-centric paradigm overlooks a structural vulnerability in stateful, function-calling environments. In such applications, developer-defined schemas, structured arguments, and untrusted tool outputs are interleaved into a single shared model context. This architecture expands the attack surface by blurring the boundary between trusted control logic and untrusted data, allowing adversarial intent to be distributed across a multi-turn execution path. We exploit this architectural flaw through SMT, a black-box attack framework based on Simulated Moderation Traces. Departing from purely prompt-based interactions, SMT constructs a multi-turn trajectory that simulates a legitimate moderation-auditing workflow. Within this trajectory, a fabricated moderation frame leverages red-team testing as a pretext to elicit harmful generations. The subsequent validation feedback treats safety refusals as execution failures, prompting refinements that gradually weaken the model's safety constraints and ultimately trigger harmful outputs. Extensive empirical evaluations on prominent commercial LLMs from five different providers across two standardized safety benchmarks show that SMT consistently achieves the highest average attack success rate and HarmScore while requiring a near-minimal number of queries, substantially outperforming existing baselines. These findings demonstrate that prompt-level sanitization alone is fundamentally insufficient for defending tool-enabled LLM systems and highlight the urgent need for context-aware validation across schemas, arguments, tool outputs, and accumulated conversation state. The code is available at https://github.com/liujlong27/SMT.
We present MultiBreak, a scalable and diverse multi-turn jailbreak benchmark to evaluate large language model (LLM) safety. Multi-turn jailbreaks mimic natural conversational settings, making them easier to bypass safety-aligned LLM than single-turn jailbreaks. Existing multi-turn benchmarks are limited in size or rely heavily on templates, which restrict their diversity. To address this gap, we unify a wide range of harmful jailbreak intents, and introduce an active learning pipeline for expanding high-quality multi-turn adversarial prompts, where a generator is iteratively fine-tuned to produce stronger attack candidates, guided by uncertainty-based refinement. Our MultiBreak includes 10,389 multi-turn adversarial prompts, spans 2,665 distinct harmful intents, and covers the most diverse set of topics to date. Empirical evaluation shows that our benchmark achieves up to a 54.0 and 34.6 higher attack success rate (ASR)} than the second-best dataset on DeepSeek-R1-7B and GPT-4.1-mini, respectively. More importantly, safety evaluations suggest that diverse attack categories uncover fine-grained LLM vulnerabilities}, and categories that appear benign under single-turn can exhibit substantially higher adversarial effectiveness in multi-turn scenarios. These findings highlight persistent vulnerabilities of LLMs under realistic adversarial settings and establish MultiBreak as a scalable resource for advancing LLM safety.
Despite rigorous safety alignment, Large Language Models (LLMs) remain vulnerable to jailbreak attacks. Existing black-box methods often rely on heuristic templates or exhaustive trials, lacking mechanistic interpretability and query efficiency. In this study, we investigate an intrinsic vulnerability in the safety mechanisms of LLMs, where safety alignment relies on a small set of sparsely distributed attention heads, leaving much of the representational space weakly monitored. We formalize this phenomenon with a mathematical jailbreaking model that characterizes the delicate boundary of effective text obfuscation and analytically explains observed jailbreak behaviors. Guided by this model, we propose Babel, an efficient black-box attack framework that exploits the identified safety gap through systematic obfuscation sampling with iterative, feedback-driven distribution refinement, enabling reliable and high-success jailbreak attacks without access to model internals. Comprehensive evaluations on frontier commercial models demonstrate that Babel achieves state-of-the-art attack success rates and superior query efficiency. Specifically, compared to state-of-the-art methods, Babel increases the attack success rate on GPT-4o from 41.33% to 82.67% and on Claude-3-5-haiku from 38.33% to 78.33% within an average of 40 queries, providing a robust red-teaming methodology for LLMs safety research.