Abstract
Automated red-teaming for LLMs often discovers narrow attack slices, missing diverse real-world threats, and yielding insufficient data for safety fine-tuning. We introduce Persona-Conditioned Adversarial Prompting (PCAP), which conditions adversarial search on diverse attacker personas (e.g., doctors, students, malicious actors) and strategy sets to explore realistic attack scenarios. By running parallel persona-conditioned searches, PCAP discovers transferable jailbreaks across different contexts and generates rich defense datasets with automatic metadata tracking. On GPT-OSS 120B, PCAP increases attack success from 57\% to 97\% while producing 2-6 more diverse prompts covering varied real-world scenarios. Critically, fine-tuning lightweight adapters on PCAP-generated data significantly improves model robustness (recall: 0.36 0.99, F1: 0.53 0.96) with minimal false positives, demonstrating a practical closed-loop approach from vulnerability discovery to automated alignment.
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