paperMay 2026Unreviewed

The Art of the Jailbreak: Formulating Jailbreak Attacks for LLM Security Beyond Binary Scoring

Ismail Hossain, Tanzim Ahad, Md Jahangir Alam, Sai Puppala, Syed Bahauddin Alam, Sajedul Talukder

Abstract

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 Jail

Framework mappings

OWASP Top 10 for LLM Applications

LLM01Prompt Injection

MITRE ATLAS

AML.T0054LLM Jailbreak

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Cite

@misc{hossain2026art,
  title = {{The Art of the Jailbreak: Formulating Jailbreak Attacks for LLM Security Beyond Binary Scoring}},
  author = {Ismail Hossain and Tanzim Ahad and Md Jahangir Alam and Sai Puppala and Syed Bahauddin Alam and Sajedul Talukder},
  year = {2026},
  month = may,
  eprint = {2605.09225},
  archivePrefix = {arXiv},
  url = {https://arxiv.org/abs/2605.09225}
}