Despite the widespread use of Transformer-based text embedding models in NLP tasks, surprising “sticky tokens” can undermine the reliability of embeddings. These tokens, when repeatedly inserted into sentences, pull sentence similarity toward a certain value, disrupting the normal distribution of embedding distances and degrading downstream performance. In this paper, we systematically investigate such anomalous tokens, formally defining them and introducing an efficient detection method, Sticky Token Detector (STD), based on sentence and token filtering. Applying STD to 40 checkpoints across 14 model families, we discover a total of 868 sticky tokens. Our analysis reveals that these tokens often originate from special or unused entries in the vocabulary, as well as fragmented subwords from multilingual corpora. Notably, their presence does not strictly correlate with model size or vocabulary size. We further evaluate how sticky tokens affect downstream tasks like clustering and retrieval, observing significant performance drops of up to 50%. Through attention-layer analysis, we show that sticky tokens disproportionately dominate the model’s internal representations, raising concerns about tokenization robustness. Our findings show the need for better tokenization strategies and model design to mitigate the impact of sticky tokens in future text embedding applications.

**Warning: This paper contains content that may involve potentially harmful behaviours, discussed strictly for research purposes.**Jailbreak attacks can hinder the safety of Large Language Model (LLM) applications, especially chatbots. Studying jailbreak techniques is an important AI red teaming task for improving the safety of these applications. In this paper, we introduce TombRaider, a novel jailbreak technique that exploits the ability to store, retrieve, and use historical knowledge of LLMs. TombRaider employs two agents, the inspector agent to extract relevant historical information and the attacker agent to generate adversarial prompts, enabling effective bypassing of safety filters. We intensively evaluated TombRaider on six popular models. Experimental results showed that TombRaider could outperform state-of-the-art jailbreak techniques, achieving nearly 100% attack success rates (ASRs) on bare models and maintaining over 55.4% ASR against defence mechanisms. Our findings highlight critical vulnerabilities in existing LLM safeguards, underscoring the need for more robust safety defences.