Benchmarking Large Language Models for Cryptanalysis and Mismatched-Generalization (2505.24621v1)

Abstract: Recent advancements in LLMs have transformed natural language understanding and generation, leading to extensive benchmarking across diverse tasks. However, cryptanalysis a critical area for data security and encryption has not yet been thoroughly explored in LLM evaluations. To address this gap, we evaluate cryptanalytic potential of state of the art LLMs on encrypted texts generated using a range of cryptographic algorithms. We introduce a novel benchmark dataset comprising diverse plain texts spanning various domains, lengths, writing styles, and topics paired with their encrypted versions. Using zero-shot and few shot settings, we assess multiple LLMs for decryption accuracy and semantic comprehension across different encryption schemes. Our findings reveal key insights into the strengths and limitations of LLMs in side-channel communication while raising concerns about their susceptibility to jailbreaking attacks. This research highlights the dual-use nature of LLMs in security contexts and contributes to the ongoing discussion on AI safety and security.