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

Large language models (LLMs) are increasingly deployed in education, healthcare, policy advising, and other interactive settings, where users engage them as sustained social interlocutors rather than one-shot query engines. This shift makes jailbreaks a growing safety threat, yet most research emphasizes single-turn prompt optimization or iterative attack refinement, leaving psychologically grounded multi-turn vulnerabilities underexplored. We present PsychJail, a psychology-guided framework for red teaming aligned LLMs through theory-grounded, multi-turn persuasion. PsychJail maps established social-psychological persuasion techniques into a tactic-conditioned attack policy. It factorizes each attacker action into a Change-of-Meaning analysis, tactic selection, and victim-visible message, operationalizing the Persuasion Knowledge Model (PKM). The policy is refined with trajectory-level reinforcement learning using a PKM-gated reward that credits early jailbreak success only when every turn contains a well-formed Change-of-Meaning analysis. Across four aligned victim models, PsychJail achieves the highest average attack success rate (87.3%) and outperforms strong single-turn and multi-turn baselines on every model. We also measure susceptibility at the action that breaks each victim, revealing four distinct model-level fingerprints that identify which persuasion levers affect each model and how broadly. These fingerprints help explain cross-model transfer asymmetry. We interpret them as four candidate psychological profiles-rationalist, credibility-driven, narrative-monoculture, and broadly persuadable-while treating this interpretation as a conjecture requiring future validation. Our findings establish psychological jailbreaks as a distinct red-teaming frontier for increasingly interactive LLMs.