LLM-Guided Prompt Evolution for Password Guessing

Passwords remain the dominant online authentication mechanism, and understanding how humans choose them is essential for defensive strength estimation and attack simulation alike. Recent learning-based approaches such as PassGAN and PassGPT have shown that deep generative models can learn password structure directly from leaked corpora. However, both train from random initialization on password data alone. The role of linguistic prior knowledge in password modeling, and what it reveals about how humans create secrets, remains largely underexplored. Here, we address this gap with PassGPT+, which adapts the linguistic prior of GPT-2 to password observations through character-aware tokenization. We also introduce PassDiffusion, the first absorbing-state discrete diffusion model for password generation, as a probe of whether non-autoregressive approaches are competitive. On the RockYou benchmark, PassGPT+ recovers 22.53% of held-out passwords at 108 guesses, a 16% relative gain over PassGPT, and retains 79% of this match rate when transferred without retraining to a disjoint 2020 leak dataset, demonstrating that linguistic priors capture persistent regularities of human password generation. PassDiffusion underperforms by two to three orders of magnitude, indicating that autoregressive modeling is substantially better matched than iterative denoising to the discrete, exact-match nature of password generation.

Jailbreak attacks -- adversarial prompts that bypass LLM alignment through purely linguistic manipulation -- pose a growing operational security threat, yet the field lacks large-scale, reproducible infrastructure for generating, categorizing, and evaluating them systematically. This paper addresses that gap with three contributions. (1) Large-scale compositional jailbreak dataset. We construct 114,000 adversarial prompts by applying 912 composing strategies to 125 harmful seed prompts from JailBreakV-28K. Every prompt is assigned to one of 14 cybersecurity attack categories (e.g., malware, phishing, privilege escalation) via a six-model majority-vote pipeline, and each strategy is ranked by effectiveness per category, enabling principled strategy selection grounded in concrete adversarial objectives. (2) Automated jailbreak generation. We instruction-fine-tune category-aware LLMs on Moderate and Optimal subsets, producing models that synthesize fluent jailbreak prompts from a harmful seed at inference time -- no templates, no gradient search. Our generators achieve perplexity 24-39 versus 40-140 for AutoDAN and AmpleGCG, with safety-filter evasion rates of 0.29-0.51 Mal (LlamaPromptGuard-2-86M), enabling controllable, scalable red-teaming under realistic adversarial conditions. (3) OPTIMUS: a training-free jailbreak evaluator. OPTIMUS is a continuous metric J(S,H) that jointly captures semantic similarity between the harmful seed and the jailbreak (S) and harmfulness probability (H) via calibrated penalty functions. Unlike binary attack success rate (ASR), OPTIMUS requires no task-specific training, generalizes across evolving strategies, and exposes a stealth-optimal regime (S*=0.57, H*=0.43) that ASR misses. Experiments across 114,000 prompts confirm that OPTIMUS separates Weak, Moderate, and Optimal jailbreaks with category-level evidence binary evaluation cannot supply.

LLM coding agents now generate code at an unprecedented scale, yet LLM-generated code introduces cybersecurity vulnerabilities into codebases without human involvement. Even when frontier models are explicitly asked to write secure production code with relevant weaknesses to avoid in context, we find that they still produce verifiable vulnerabilities on average 23% of the time across a corpus of 250 benign coding prompts. We introduce SecureForge, an automated pipeline that both audits security risks of frontier models and produces auditing-informed secure system prompts that reduce output security vulnerabilities while maintaining unit test performance. SecureForge first identifies benign prompts that produce statically detectable vulnerabilities, and then amplifies them into a large synthetic prompt corpus of diverse scenarios using a Markovian sampling technique to jointly maintain error rates and prompt diversity. This corpus is then used to iteratively optimize the system prompts to reduce output security vulnerabilities. On frontier models, SecureForge yields a statistically significant Pareto improvement in both unit test success and output security, with output vulnerabilities reduced by up to 48%. The resulting system prompts transfer zero-shot to in-the-wild coding agent prompts, without any exposure to real user prompt distributions during optimization.