# Benchmarking Large Language Models for Cryptanalysis and Side-Channel Vulnerabilities

arXiv: https://arxiv.org/abs/2505.24621 · HTML: https://mlsanity.com/paper/2505.24621/

## Key facts

- Cited by 5 papers in the map (data through 14 Oct 2026).
- Builds on 20 of its 55 references that are in the map.
- First posted on arXiv 30 May 2025.

## Builds on (most cited first, 20 of 20)

- [Language Models are Few-Shot Learners](https://mlsanity.com/paper/2005.14165/) (2020)
- [GPT-4 Technical Report](https://mlsanity.com/paper/2303.08774/) (2023)
- [BERTScore: Evaluating Text Generation with BERT](https://mlsanity.com/paper/1904.09675/) (2019)
- [Jailbroken: How Does LLM Safety Training Fail?](https://mlsanity.com/paper/2307.02483/) (2023)
- [Baseline Defenses for Adversarial Attacks Against Aligned Language Models](https://mlsanity.com/paper/2309.00614/) (2023)
- [Jailbreaking Leading Safety-Aligned LLMs with Simple Adaptive Attacks](https://mlsanity.com/paper/2404.02151/) (2024)
- [Detecting Language Model Attacks with Perplexity](https://mlsanity.com/paper/2308.14132/) (2023)
- [GPT-4 Is Too Smart To Be Safe: Stealthy Chat with LLMs via Cipher](https://mlsanity.com/paper/2308.06463/) (2023)
- [PandaLM: An Automatic Evaluation Benchmark for LLM Instruction Tuning Optimization](https://mlsanity.com/paper/2306.05087/) (2023)
- [Exploiting Programmatic Behavior of LLMs: Dual-Use Through Standard Security Attacks](https://mlsanity.com/paper/2302.05733/) (2023)
- [SafeDecoding: Defending against Jailbreak Attacks via Safety-Aware Decoding](https://mlsanity.com/paper/2402.08983/) (2024)
- [ArtPrompt: ASCII Art-based Jailbreak Attacks against Aligned LLMs](https://mlsanity.com/paper/2402.11753/) (2024)
- [Defending Against Alignment-Breaking Attacks via Robustly Aligned LLM](https://mlsanity.com/paper/2309.14348/) (2023)
- [Defending Large Language Models Against Jailbreak Attacks via Layer-specific Editing](https://mlsanity.com/paper/2405.18166/) (2024)
- [TELeR: A General Taxonomy of LLM Prompts for Benchmarking Complex Tasks](https://mlsanity.com/paper/2305.11430/) (2023)
- [When "Competency" in Reasoning Opens the Door to Vulnerability: Jailbreaking LLMs via Novel Complex Ciphers](https://mlsanity.com/paper/2402.10601/) (2024)
- [SALSA: Attacking Lattice Cryptography with Transformers](https://mlsanity.com/paper/2207.04785/) (2022)
- [Llama Guard 3-1B-INT4: Compact and Efficient Safeguard for Human-AI Conversations](https://mlsanity.com/paper/2411.17713/) (2024)
- [Two Heads are Better than One: Nested PoE for Robust Defense Against Multi-Backdoors](https://mlsanity.com/paper/2404.02356/) (2024)
- [Unsupervised Cipher Cracking Using Discrete GANs](https://mlsanity.com/paper/1801.04883/) (2018)

## Built on by (most cited first, 5 of 5)

- [Should LLM Safety Be More Than Refusing Harmful Instructions?](https://mlsanity.com/paper/2506.02442/) (2025)
- [CryptoQA: A Large-scale Question-answering Dataset for AI-assisted Cryptography](https://mlsanity.com/paper/2512.02625/) (2025)
- [SafeConstellations: Mitigating Over-Refusals in LLMs Through Task-Aware Representation Steering](https://mlsanity.com/paper/2508.11290/) (2025)
- [Do Clinical Question Answering Systems Really Need Specialised Medical Fine Tuning?](https://mlsanity.com/paper/2601.12812/) (2026)
- [CESBench: Benchmarking Large Language Models on Cryptographic Engineering Security for IoT Devices](https://mlsanity.com/paper/2609.21344/) (2026)

## Abstract (arXiv)

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.