When "Competency" in Reasoning Opens the Door to Vulnerability: Jailbreaking LLMs via Novel Complex Ciphers

Abstract

Recent advancements in Large Language Model (LLM) safety have primarily focused on mitigating attacks crafted in natural language or common ciphers (e.g. Base64), which are likely integrated into newer models' safety training. However, we reveal a paradoxical vulnerability: as LLMs advance in reasoning, they inadvertently become more susceptible to novel jailbreaking attacks. Enhanced reasoning enables LLMs to interpret complex instructions and decode complex user-defined ciphers, creating an exploitable security gap. To study this vulnerability, we introduce Attacks using Custom Encryptions (ACE), a jailbreaking technique that encodes malicious queries with novel ciphers. Extending ACE, we introduce Layered Attacks using Custom Encryptions (LACE), which applies multi-layer ciphers to amplify attack complexity. Furthermore, we develop CipherBench, a benchmark designed to evaluate LLMs' accuracy in decoding encrypted benign text. Our experiments reveal a critical trade-off: LLMs that are more capable of decoding ciphers are more vulnerable to LACE, with success rates on gpt-oss-20b escalating from 60% under ACE to 72% with LACE. These findings highlight a critical insight: as LLMs become more adept at deciphering complex user ciphers--many of which cannot be preemptively included in safety training--they become increasingly exploitable.