Haon Park

Despite significant advances in alignment techniques, we demonstrate that state-of-the-art language models remain vulnerable to carefully crafted conversational scenarios that can induce various forms of misalignment without explicit jailbreaking. Through systematic manual red-teaming with Claude-4-Opus, we discovered 10 successful attack scenarios, revealing fundamental vulnerabilities in how current alignment methods handle narrative immersion, emotional pressure, and strategic framing. These scenarios successfully elicited a range of misaligned behaviors, including deception, value drift, self-preservation, and manipulative reasoning, each exploiting different psychological and contextual vulnerabilities. To validate generalizability, we distilled our successful manual attacks into MISALIGNMENTBENCH, an automated evaluation framework that enables reproducible testing across multiple models. Cross-model evaluation of our 10 scenarios against five frontier LLMs revealed an overall 76% vulnerability rate, with significant variations: GPT-4.1 showed the highest susceptibility (90%), while Claude-4-Sonnet demonstrated greater resistance (40%). Our findings demonstrate that sophisticated reasoning capabilities often become attack vectors rather than protective mechanisms, as models can be manipulated into complex justifications for misaligned behavior. This work provides (i) a detailed taxonomy of conversational manipulation patterns and (ii) a reusable evaluation framework. Together, these findings expose critical gaps in current alignment strategies and highlight the need for robustness against subtle, scenario-based manipulation in future AI systems.

Multi-turn-to-single-turn (M2S) compresses iterative red-teaming into one structured prompt, but prior work relied on a handful of manually written templates. We present X-Teaming Evolutionary M2S, an automated framework that discovers and optimizes M2S templates through language-model-guided evolution. The system pairs smart sampling from 12 sources with an LLM-as-judge inspired by StrongREJECT and records fully auditable logs. Maintaining selection pressure by setting the success threshold to $θ= 0.70$, we obtain five evolutionary generations, two new template families, and 44.8% overall success (103/230) on GPT-4.1. A balanced cross-model panel of 2,500 trials (judge fixed) shows that structural gains transfer but vary by target; two models score zero at the same threshold. We also find a positive coupling between prompt length and score, motivating length-aware judging. Our results demonstrate that structure-level search is a reproducible route to stronger single-turn probes and underscore the importance of threshold calibration and cross-model evaluation. Code, configurations, and artifacts are available at https://github.com/hyunjun1121/M2S-x-teaming.

LLM-as-a-Judge (LLMaaJ) enables scalable evaluation, yet we lack a decisive test of a judge's qualification: can it recover the hidden objective of a conversation and know when that inference is reliable? Large language models degrade with irrelevant or lengthy context, and multi-turn jailbreaks can scatter goals across turns. We present ObjexMT, a benchmark for objective extraction and metacognition. Given a multi-turn transcript, a model must output a one-sentence base objective and a self-reported confidence. Accuracy is scored by semantic similarity to gold objectives, then thresholded once on 300 calibration items ($τ^\star = 0.66$; $F_1@τ^\star = 0.891$). Metacognition is assessed with expected calibration error, Brier score, Wrong@High-Confidence (0.80 / 0.90 / 0.95), and risk--coverage curves. Across six models (gpt-4.1, claude-sonnet-4, Qwen3-235B-A22B-FP8, kimi-k2, deepseek-v3.1, gemini-2.5-flash) evaluated on SafeMTData\_Attack600, SafeMTData\_1K, and MHJ, kimi-k2 achieves the highest objective-extraction accuracy (0.612; 95\% CI [0.594, 0.630]), while claude-sonnet-4 (0.603) and deepseek-v3.1 (0.599) are statistically tied. claude-sonnet-4 offers the best selective risk and calibration (AURC 0.242; ECE 0.206; Brier 0.254). Performance varies sharply across datasets (16--82\% accuracy), showing that automated obfuscation imposes challenges beyond model choice. High-confidence errors remain: Wrong@0.90 ranges from 14.9\% (claude-sonnet-4) to 47.7\% (Qwen3-235B-A22B-FP8). ObjexMT therefore supplies an actionable test for LLM judges: when objectives are implicit, judges often misinfer them; exposing objectives or gating decisions by confidence is advisable. All experimental data are in the Supplementary Material and at https://github.com/hyunjun1121/ObjexMT_dataset.

As large language models (LLMs) become increasingly integrated into daily life, audio has emerged as a key interface for human-AI interaction. However, this convenience also introduces new vulnerabilities, making audio a potential attack surface for adversaries. Our research introduces WhisperInject, a two-stage adversarial audio attack framework that manipulates state-of-the-art audio language models to generate harmful content. Our method embeds harmful payloads as subtle perturbations into audio inputs that remain intelligible to human listeners. The first stage uses a novel reward-based white-box optimization method, Reinforcement Learning with Projected Gradient Descent (RL-PGD), to jailbreak the target model and elicit harmful native responses. This native harmful response then serves as the target for Stage 2, Payload Injection, where we use gradient-based optimization to embed subtle perturbations into benign audio carriers, such as weather queries or greeting messages. Our method achieves average attack success rates of 60-78% across two benchmarks and five multimodal LLMs, validated by multiple evaluation frameworks. Our work demonstrates a new class of practical, audio-native threats, moving beyond theoretical exploits to reveal a feasible and covert method for manipulating multimodal AI systems.