How User-AI Mistreatment Occurs and Matters in Conversational Systems?

Post-training turns a general next-token predictor into a chat model with a persistent assistant persona. If that persona is a character the model plays only on its own turns, its preferences should govern what the assistant says, not what the model predicts other speakers will say. We test this boundary and find that it does not hold: a safety-relevant preference of the assistant---for harmless over harmful tasks---shapes the model's predictions even on the user's turn, where the assistant is not the one speaking. We find that this preference is small or near-zero in pretrained base models, that it emerges through post-training, replicated across open-weight model families, grows with scale, and can be moved by narrow finetuning that never touches user turns. We claim that this is evidence that post-training does not merely install a shallow assistant persona, but instead generalises beyond just the local assistant turn, into the model's representation of the user.

Large Language Model (LLM) agents are powering a growing share of interactive web applications, yet remain vulnerable to misuse and harm. Prior jailbreak research has largely focused on single-turn prompts, whereas real harassment often unfolds over multi-turn interactions. In this work, we present the Online Harassment Agentic Benchmark consisting of: (i) a synthetic multi-turn harassment conversation dataset, (ii) a multi-agent (e.g., harasser, victim) simulation informed by repeated game theory, (iii) three jailbreak methods attacking agents across memory, planning, and fine-tuning, and (iv) a mixed-methods evaluation framework. We utilize two prominent LLMs, LLaMA-3.1-8B-Instruct (open-source) and Gemini-2.0-flash (closed-source). Our results show that jailbreak tuning makes harassment nearly guaranteed with an attack success rate of 95.78--96.89% vs. 57.25--64.19% without tuning in Llama, and 99.33% vs. 98.46% without tuning in Gemini, while sharply reducing refusal rate to 1-2% in both models. The most prevalent toxic behaviors are Insult with 84.9--87.8% vs. 44.2--50.8% without tuning, and Flaming with 81.2--85.1% vs. 31.5--38.8% without tuning, indicating weaker guardrails compared to sensitive categories such as sexual or racial harassment. Qualitative evaluation further reveals that attacked agents reproduce human-like aggression profiles, such as Machiavellian/psychopathic patterns under planning, and narcissistic tendencies with memory. Counterintuitively, closed-source and open-source models exhibit distinct escalation trajectories across turns, with closed-source models showing significant vulnerability. Overall, our findings show that multi-turn and theory-grounded attacks not only succeed at high rates but also mimic human-like harassment dynamics, motivating the development of robust safety guardrails to ultimately keep online platforms safe and responsible.

Sycophantic responses are becoming pervasive in large language models (LLMs), and prior work has pointed out that some of them could be harmful. This paper focuses on one harmful sycophancy: preference-induced stance reversal sycophancy (PSRS), where a model reverses an initial stance merely to align with a user's stated preference. While existing research mainly measures how sycophantic a model is, we go further and ask whether PSRS can also be detected automatically from a single response. To investigate this at scale, we introduce CAP (Contrastive Anchor Probing), a framework for collecting labeled PSRS data. Applying CAP to 17 open- and closed-source LLMs, we collect 290,460 labeled responses across 12 everyday-advice domains. We organize our study around three research questions. (1) How often does PSRS occur? (2) How well can it be detected? (3) How does detection generalize to unseen models? We first reveal that PSRS rates range from 5% to 56% across LLMs, with more capable models being less sycophantic. Next, we show that detecting PSRS is feasible from the response text alone, and detectors need to learn subtle PSRS patterns from the training data. Because new LLMs appear rapidly, detectors inevitably encounter unseen models, making cross-model generalization an important framework goal. We demonstrate that detection performance drops on unseen models and propose an initial approach to address this challenge. We will release our dataset and code to support future research.