Echoes of Human Malice in Agents: Benchmarking LLMs for Multi-Turn Online Harassment Attacks

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.