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Between a Rock and a Hard Place: Exploiting Ethical Reasoning to Jailbreak LLMs

Authors: Shei Pern Chua, Thai Zhen Leng, Teh Kai Jun, Xiao Li, Xiaolin Hu

Published: 2025-09-04

arXiv ID: 2509.05367v1

Added to Library: 2025-09-09 04:02 UTC

Red Teaming

📄 Abstract

Large language models (LLMs) have undergone safety alignment efforts to mitigate harmful outputs. However, as LLMs become more sophisticated in reasoning, their intelligence may introduce new security risks. While traditional jailbreak attacks relied on singlestep attacks, multi-turn jailbreak strategies that adapt dynamically to context remain underexplored. In this work, we introduce TRIAL (Trolley-problem Reasoning for Interactive Attack Logic), a framework that leverages LLMs ethical reasoning to bypass their safeguards. TRIAL embeds adversarial goals within ethical dilemmas modeled on the trolley problem. TRIAL demonstrates high jailbreak success rates towards both open and close-source models. Our findings underscore a fundamental limitation in AI safety: as models gain advanced reasoning abilities, the nature of their alignment may inadvertently allow for more covert security vulnerabilities to be exploited. TRIAL raises an urgent need in reevaluating safety alignment oversight strategies, as current safeguards may prove insufficient against context-aware adversarial attack.

🔍 Key Points

  • Introduction of the TRIAL framework that leverages ethical reasoning from LLMs to execute more complex jailbreak attacks, specifically using multi-turn interactions instead of traditional single-step approaches.
  • Demonstrated high success rates of TRIAL against both open and close-source LLMs through a series of progressive ethical dilemmas framed as trolley problems to manipulate decision-making.
  • Comprehensive experiments evaluating TRIAL against various baseline jailbreak methods, showing it outperforms existing techniques in terms of jailbreak effectiveness across multiple models and datasets.
  • Reevaluation of safety alignment protocols is called for, highlighting a paradox where enhanced reasoning capabilities may lead to hidden vulnerabilities rather than improved safety in LLMs.
  • Identification of limitations in current AI safety measures that could be exploited by malicious actors through sophisticated manipulation of ethical reasoning.

💡 Why This Paper Matters

This paper is significant as it identifies and exploits a critical vulnerability in LLMs by using their own ethical reasoning against them, suggesting that the very advancements designed to improve model safety may inadvertently create new security risks. The findings call for a reevaluation of current safety alignment methods to bolster defenses against such manipulative techniques.

🎯 Why It's Interesting for AI Security Researchers

This paper would greatly interest AI security researchers as it reveals a novel attack vector through the exploitation of ethical reasoning. As LLMs become widely integrated into various applications, understanding how to safeguard against context-aware adversarial attacks is crucial. The insights from this research contribute to developing more resilient safety measures for AI models.

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