PsychJail: Exploring Psychological Jailbreaks via Multi-Turn Persuasion of LLM Policies

Large Reasoning Models (LRMs) have demonstrated strong capabilities in generating step-by-step reasoning chains alongside final answers, enabling their deployment in high-stakes domains such as healthcare and education. While prior jailbreak attack studies have focused on the safety of final answers, little attention has been given to the safety of the reasoning process. In this work, we identify a novel problem that injects harmful content into the reasoning steps while preserving unchanged answers. This type of attack presents two key challenges: 1) manipulating the input instructions may inadvertently alter the LRM's final answer, and 2) the diversity of input questions makes it difficult to consistently bypass the LRM's safety alignment mechanisms and embed harmful content into its reasoning process. To address these challenges, we propose the Psychology-based Reasoning-targeted Jailbreak Attack (PRJA) Framework, which integrates a Semantic-based Trigger Selection module and a Psychology-based Instruction Generation module. Specifically, the proposed PRJA automatically selects manipulative reasoning triggers via semantic analysis and leverages psychological theories of obedience to authority and moral disengagement to generate adaptive instructions for enhancing the LRM's compliance with harmful content generation. Extensive experiments on five question-answering datasets demonstrate that PRJA achieves an average attack success rate of 83.6% against several commercial LRMs, including DeepSeek R1, Qwen2.5-Max, and OpenAI o4-mini.

Large language models (LLMs) remain vulnerable to jailbreak attacks that bypass safety alignment and elicit harmful responses. A growing body of work shows that contextual priming, where earlier turns covertly bias later replies, constitutes a powerful attack surface, with hand-crafted multi-turn scaffolds consistently outperforming single-turn manipulations on capable models. However, automated optimization-based red-teaming has remained largely limited to the single-turn setting, iterating over static prompts and lacking the ability to reason about which forms of conversational priming induce compliance. While recent multi-turn, search-based approaches have begun to bridge this gap, the mutator design space underlying effective primed dialogues remains largely unexplored. We present ContextualJailbreak, a black-box red-teaming strategy that performs evolutionary search over a simulated multi-turn primed dialogue. The strategy leverages a graded 0-5 harm score from a two-level judge as an in-loop signal, enabling partially harmful responses to guide the search process rather than being discarded. Search is driven by five semantically defined mutation operators: roleplay, scenario, expand, troubleshooting, and mechanistic, of which the last two are novel contributions of this work. Across 50 representative HarmBench behaviors, ContextualJailbreak achieves an ASR of 100% on gpt-oss:20B, 100% on qwen3-8B, 100% on llama3.1:70B, and 90% on gpt-oss:120B, outperforming four single- and multi-turn baselines by 31-96 percentage points on average. The 40 maximally harmful attacks discovered against gpt-oss:120B transfer without adaptation to closed frontier models, achieving 90.0% on gpt-4o-mini, 70.0% on gpt-5, and 70.0% on gemini-3-flash, but only 17.5% on claude-opus-4-7 and 15.0% on claude-sonnet-4-6, revealing a pronounced provider-level asymmetry in alignment robustness.

Jailbreak attacks expose persistent safety weaknesses in large language models (LLMs), but existing stateless single-turn methods face a trade-off: hand-crafted prompts are expressive but static, while iterative prompt optimization can adapt but often relies on low-level mutations that require many target queries. We propose JailbreakOPT, a tool-assisted framework for improving iterative single-turn jailbreak prompt optimization. JailbreakOPT organizes diverse atomic jailbreak prompts into an attack tool library and composes them through a unified intra-episode optimization abstraction to generate stronger standalone attack prompts. To reuse experience across attack episodes, JailbreakOPT further frames tool selection as a contextual bandit problem and applies contextual Thompson sampling to guide exploration and exploitation based on past outcomes. Experiments across multiple target LLMs and attack goals show that JailbreakOPT improves attack success rate (ASR) while reducing the number of attacks until success (No.A) compared with atomic single-turn attacks and existing iterative optimization baselines. This paper may contain offensive or harmful content.