Detecting Fluent Optimization-Based Adversarial Prompts via Sequential Entropy Changes

Multi-turn prompt injection follows a known attack path -- trust-building, pivoting, escalation but text-level defenses miss covert attacks where individual turns appear benign. We show this attack path leaves an activation-level signature in the model's residual stream: each phase shift moves the activation, producing a total path length far exceeding benign conversations. We call this adversarial restlessness. Five scalar trajectory features capturing this signal lift conversation-level detection from 76.2% to 93.8% on synthetic held-out data. The signal replicates across four model families (24B-70B); probes are model-specific and do not transfer across architectures. Generalization is source-dependent: leave-one-source-out evaluation shows each of synthetic, LMSYS-Chat-1M, and SafeDialBench captures distinct attack distributions, with detection on real-world LMSYS reaching 47-71% when its distribution is represented in training. Combined three-source training achieves 89.4% detection at 2.4% false positive rate on a held-out mixed set. We further show that three-phase turn-level labels(benign/pivoting/adversarial) unique to our synthetic dataset are essential: binary conversation-level labels produce 50-59% false positives. These results establish adversarial restlessness as a reliable activation-level signal and characterize the data requirements for practical deployment.

We investigate which language model evasion attacks survive state-of-the-art adversarial fine-tuning, developing strategies that sweep the top 5 positions on the ELOQUENT 2026 Voight-Kampff leaderboard. While adversarial fine-tuning trivially closes the 2025 winning evasion recipes, we uncover a fundamental asymmetry in detector vulnerability: pushing generated text out of the detector's training distribution reliably defeats adversarial detection, whereas pulling it into the distribution (e.g., mimicking human training data) fails completely. Exploiting this, we introduce two novel out-of-distribution attack families - cross-decade register attacks and modernist stream-of-consciousness form. Both strategies easily bypass adversarial closure, achieving up to approximately 50x higher fool rates than previous methods while preserving naturalness. Furthermore, experiments show that the obvious deployer countermeasure (augmenting training data with period prose) fails to close the vulnerability. Our findings show that the tested detector families, including adversarially fine-tuned ones, exhibit persistent vulnerabilities under structural out-of-distribution shifts, a mechanism that directly powers our leading competition performance.

Existing white-box jailbreak attacks against aligned LLMs typically append discrete adversarial suffixes to the user prompt, which visibly alters the prompt and operates in a combinatorial token space. Prior work has avoided directly optimizing the embeddings of the original prompt tokens, presumably because perturbing them risks destroying the prompt's semantic content. We propose Prompt Embedding Optimization (PEO), a multi-round white-box jailbreak that directly optimizes the embeddings of the original prompt tokens without appending any adversarial tokens, and show that the concern is unfounded: the optimized embeddings remain close enough to their originals that the visible prompt string is preserved exactly after nearest-token projection, and quantitative analysis shows the model's responses stay on topic for the large majority of prompts. PEO combines continuous embedding-space optimization with structured continuation targets and an adaptive failure-focused schedule. Counterintuitively, later PEO rounds can benefit from heuristic composite response scaffolds that are not natural standalone templates, yet ASR-Judge shows that the resulting gains are not merely empty formatting or scaffold-only outputs. Across two standard harmful-behavior benchmarks and competing white-box attacks spanning discrete suffix search, appended adversarial embeddings, and search-based adversarial generation, PEO outperforms all of them in our experiments.