Benchmarking Large Language Models for Cryptanalysis and Side-Channel Vulnerabilities

Utsav Maskey, Chencheng Zhu, Usman Naseem
5/30/2025
cs.CL

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Abstract

Recent advancements in large language models (LLMs) have transformed natural language understanding and generation, leading to extensive benchmarking across diverse tasks. However, cryptanalysis - a critical area for data security and its connection to LLMs' generalization abilities - remains underexplored in LLM evaluations. To address this gap, we evaluate the cryptanalytic potential of state-of-the-art LLMs on ciphertexts produced by a range of cryptographic algorithms. We introduce a benchmark dataset of diverse plaintexts, spanning multiple domains, lengths, writing styles, and topics, paired with their encrypted versions. Using zero-shot and few-shot settings along with chain-of-thought prompting, we assess LLMs' decryption success rate and discuss their comprehension abilities. Our findings reveal key insights into LLMs' strengths and limitations in side-channel scenarios and raise concerns about their susceptibility to under-generalization-related attacks. This research highlights the dual-use nature of LLMs in security contexts and contributes to the ongoing discussion on AI safety and security.

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@article{maskey2025benchmarking,
  title  = {Benchmarking Large Language Models for Cryptanalysis and Side-Channel Vulnerabilities},
  author = {Utsav Maskey and Chencheng Zhu and Usman Naseem},
  year   = {2025},
  eprint = {2505.24621},
  archivePrefix = {arXiv},
  url    = {http://arxiv.org/abs/2505.24621v2}
}

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