What Intermediate Layers Know: Detecting Jailbreaks from Entropy Dynamics

Jailbreak attacks reveal a persistent weakness in aligned Large Language Models: carefully crafted prompts can elicit policy-violating responses despite safety training. While most defenses operate at the prompt or output level, it remains unclear how harmful intent is encoded within the model's internal representations. We investigate this question by analyzing token-level predictive entropy trajectories across layers of a frozen LLM using the logit lens. We find that static aggregate statistics of prompt-level entropy (e.g., mean, variance) carry little discriminative signal, whereas features capturing how entropy evolves across token positions, such as monotonic rank-based trend scores, are substantially more informative. Importantly, this signal is not uniform across model depth: it is concentrated in intermediate layers and degrades at the final layer, indicating that jailbreak-relevant structure is most pronounced in mid-network representations rather than at the output head. Across multiple models (Llama, Qwen, Gemma) and adversarial benchmarks, these entropy dynamics provide architecture-consistent separation without additional training. Together, our findings show that jailbreak behavior is reflected in structured intermediate uncertainty dynamics, clarifying both which entropy-derived features encode harmful intent and where in the network that signal is most pronounced.

Stress-testing Machine Generated Text Detection: Shifting Language Models Writing Style to Fool Detectors

Recent advancements in Generative AI and Large Language Models (LLMs) have enabled the creation of highly realistic synthetic content, raising concerns about the potential for malicious use, such as misinformation and manipulation. Moreover, detecting Machine-Generated Text (MGT) remains challenging due to the lack of robust benchmarks that assess generalization to real-world scenarios. In this work, we present a pipeline to test the resilience of state-of-the-art MGT detectors (e.g., Mage, Radar, LLM-DetectAIve) to linguistically informed adversarial attacks. To challenge the detectors, we fine-tune language models using Direct Preference Optimization (DPO) to shift the MGT style toward human-written text (HWT). This exploits the detectors' reliance on stylistic clues, making new generations more challenging to detect. Additionally, we analyze the linguistic shifts induced by the alignment and which features are used by detectors to detect MGT texts. Our results show that detectors can be easily fooled with relatively few examples, resulting in a significant drop in detection performance. This highlights the importance of improving detection methods and making them robust to unseen in-domain texts.