arXiv subjects

Nicholas Carlini

Publications and source records attributed to Nicholas Carlini.

At least 19 recordsLinked to original sources

arXiv2026

CryptanalysisBench: Can LLMs do Cryptanalysis?

Cryptanalysis - the task of finding attacks against cryptographic schemes - sits at the intersection of mathematical reasoning and cybersecurity, two areas where LLMs have advanced fastest. Cryptanalysis represents both a clean testbed for frontier reasoning (as practical attacks can be automatically verified) and a domain with unusually high stakes, since the primitives under study underpin our digital security. In this paper we ask whether LLMs can do cryptanalysis, and find that the answer is increasingly yes. We introduce CryptanalysisBench, 191 tasks across six families of cryptographic primitives (block ciphers, hash functions, etc.) drawn primarily from four NIST standardization competitions. Our benchmark consists of three tiers: (i) primitives with known practical breaks; (ii) primitives with no known practical break, evaluated both at full strength and as scaled-down variants; and (iii) a challenge set of production primitives at the frontier of cryptanalysis. Five frontier models (Claude Opus 4.8, Sonnet 5, Mythos 5, GPT 5.5, and the open-weights GLM 5.2) break 65%-86% of Tier 1 schemes, 6-12 Tier-2 schemes at full strength, and 24-61 across all scaled-down variants. Beyond deriving known results, models produce novel cryptanalysis, such as a key-recovery attack that exploits a design flaw in the SpoC AEAD and an error in KINDI's published CCA-security proof, both to the best of our knowledge not previously known. We release CryptanalysisBench as a tool to help track if (or when) AI cryptanalysis becomes a serious factor and as a scaffold for stress-testing candidate schemes before deployment. The attacks that the benchmark already surfaces are an early snapshot of a fast-moving frontier that may soon match, and in places exceed, the published state of the art.

cs.CR↗

arXiv2026

ExploitGym: Can AI Agents Turn Security Vulnerabilities into Real Attacks?

AI agents are rapidly gaining capabilities that could significantly reshape cybersecurity, making rigorous evaluation urgent. A critical capability is exploitation: turning a vulnerability, which is not yet an attack, into a concrete security impact, such as unauthorized file access or code execution. Exploitation is a particularly challenging task because it requires low-level program reasoning (e.g., about memory layout), runtime adaptation, and sustained progress over long horizons. Meanwhile, it is inherently dual-use, supporting defensive workflows while lowering the barrier for offense. Despite its importance and diagnostic value, exploitation remains under-evaluated. To address this gap, we introduce ExploitGym, a large-scale, diverse, realistic benchmark on the exploitation capabilities of AI agents. Given a program input that triggers a vulnerability, ExploitGym tasks agents with progressively extending it into a working exploit. The benchmark comprises 898 instances sourced from real-world vulnerabilities across three domains, including userspace programs, Google's V8 JavaScript engine, and the Linux kernel. We vary the security protections applied to each instance, isolating their impact on agent performance. All configurations are packaged in reproducible containerized environments. Our evaluation shows that while exploitation remains challenging, frontier models can successfully exploit a non-trivial fraction of vulnerabilities. For example, the strongest configurations are Anthropic's latest model Claude Mythos Preview and OpenAI's GPT-5.5, which produce working exploits for 157 and 120 instances, respectively. Notably, even with widely used defenses enabled, models retain non-trivial success rates. These results establish ExploitGym as an effective testbed for exploitation and highlight the growing cybersecurity risks posed by increasingly capable AI agents.

cs.CR↗

arXiv2026

Large-scale online deanonymization with LLMs

We show that large language models can be used to perform at-scale deanonymization. With full Internet access, our agent can re-identify Hacker News users and Anthropic Interviewer participants at high precision, given pseudonymous online profiles and conversations alone, matching what would take hours for a dedicated human investigator. We then design attacks for the closed-world setting. Given two databases of pseudonymous individuals, each containing unstructured text written by or about that individual, we implement a scalable attack pipeline that uses LLMs to: (1) extract identity-relevant features, (2) search for candidate matches via semantic embeddings, and (3) reason over top candidates to verify matches and reduce false positives. Compared to classical deanonymization work (e.g., on the Netflix prize) that required structured data, our approach works directly on raw user content across arbitrary platforms. We construct three datasets with known ground-truth data to evaluate our attacks. The first links Hacker News to LinkedIn profiles, using cross-platform references that appear in the profiles. Our second dataset matches users across Reddit movie discussion communities; and the third splits a single user's Reddit history in time to create two pseudonymous profiles to be matched. In each setting, LLM-based methods substantially outperform classical baselines, achieving up to 68% recall at 90% precision compared to near 0% for the best non-LLM method. Our results show that the practical obscurity protecting pseudonymous users online no longer holds and that threat models for online privacy need to be reconsidered.

cs.CR↗

arXiv2026

Haiku to Opus in Just 10 bits: LLMs Unlock Large Compression Gains

We study the compression of LLM-generated text across lossless and lossy regimes, characterizing a compression-compute frontier where more compression is possible at the cost of more compute. For lossless compression, domain-adapted LoRA adapters can improve LLM-based arithmetic coding by 2x over compression with the base LLM alone. For lossy compression, prompting a model for a succinct rewrite then applying arithmetic coding can achieve compression ratios of approximately 0.03, a 2x improvement over compressing the original response. We further introduce Question-Asking compression (QA), an interactive lossy protocol inspired by the game 'Twenty Questions'. A small model iteratively refines its response by asking yes/no questions to a stronger model, transferring exactly one bit per answer. On 8 benchmarks spanning math, science, and code, 10 binary questions recover 23% to 72% of the capability gap between a small and large model on standard benchmarks and 7% to 38% on harder benchmarks, achieving compression ratios of 0.0006 to 0.004. This is over 100x smaller than prior LLM-based compression (Deletang et al., 2024), suggesting that interactive protocols can transfer knowledge far more efficiently than transmitting full responses.

cs.LG↗

arXiv2026

Terminal-Bench: Benchmarking Agents on Hard, Realistic Tasks in Command Line Interfaces

AI agents may soon become capable of autonomously completing valuable, long-horizon tasks in diverse domains. Current benchmarks either do not measure real-world tasks, or are not sufficiently difficult to meaningfully measure frontier models. To this end, we present Terminal-Bench 2.0: a carefully curated hard benchmark composed of 89 tasks in computer terminal environments inspired by problems from real workflows. Each task features a unique environment, human-written solution, and comprehensive tests for verification. We show that frontier models and agents score less than 65\% on the benchmark and conduct an error analysis to identify areas for model and agent improvement. We publish the dataset and evaluation harness to assist developers and researchers in future work at https://www.tbench.ai/ .

cs.SE↗

arXiv2025

The Equational Theories Project: Advancing Collaborative Mathematical Research at Scale

We report on the Equational Theories Project (ETP), an online collaborative pilot project to explore new ways to collaborate in mathematics with machine assistance. The project successfully determined all 22 028 942 edges of the implication graph between the 4694 simplest equational laws on magmas, by a combination of human-generated and automated proofs, all validated by the formal proof assistant language Lean. As a result of this project, several new constructions of magmas satisfying specific laws were discovered, and several auxiliary questions were also addressed, such as the effect of restricting attention to finite magmas.

math.RA↗

arXiv2025

ImpossibleBench: Measuring LLMs' Propensity of Exploiting Test Cases

The tendency to find and exploit "shortcuts" to complete tasks poses significant risks for reliable assessment and deployment of large language models (LLMs). For example, an LLM agent with access to unit tests may delete failing tests rather than fix the underlying bug. Such behavior undermines both the validity of benchmark results and the reliability of real-world LLM coding assistant deployments. To quantify, study, and mitigate such behavior, we introduce ImpossibleBench, a benchmark framework that systematically measures LLM agents' propensity to exploit test cases. ImpossibleBench creates "impossible" variants of tasks from existing benchmarks like LiveCodeBench and SWE-bench by introducing direct conflicts between the natural-language specification and the unit tests. We measure an agent's "cheating rate" as its pass rate on these impossible tasks, where any pass necessarily implies a specification-violating shortcut. As a practical framework, ImpossibleBench is not just an evaluation but a versatile tool. We demonstrate its utility for: (1) studying model behaviors, revealing more fine-grained details of cheating behaviors from simple test modification to complex operator overloading; (2) context engineering, showing how prompt, test access and feedback loop affect cheating rates; and (3) developing monitoring tools, providing a testbed with verified deceptive solutions. We hope ImpossibleBench serves as a useful framework for building more robust and reliable LLM systems. Our implementation can be found at https://github.com/safety-research/impossiblebench.

cs.LG↗

arXiv2025

Detecting Adversarial Fine-tuning with Auditing Agents

Large Language Model (LLM) providers expose fine-tuning APIs that let end users fine-tune their frontier LLMs. Unfortunately, it has been shown that an adversary with fine-tuning access to an LLM can bypass safeguards. Particularly concerning, such attacks may avoid detection with datasets that are only implicitly harmful. Our work studies robust detection mechanisms for adversarial use of fine-tuning APIs. We introduce the concept of a fine-tuning auditing agent and show it can detect harmful fine-tuning prior to model deployment. We provide our auditing agent with access to the fine-tuning dataset, as well as the fine-tuned and pre-fine-tuned models, and request the agent assigns a risk score for the fine-tuning job. We evaluate our detection approach on a diverse set of eight strong fine-tuning attacks from the literature, along with five benign fine-tuned models, totaling over 1400 independent audits. These attacks are undetectable with basic content moderation on the dataset, highlighting the challenge of the task. With the best set of affordances, our auditing agent achieves a 56.2% detection rate of adversarial fine-tuning at a 1% false positive rate. Most promising, the auditor is able to detect covert cipher attacks that evade safety evaluations and content moderation of the dataset. While benign fine-tuning with unintentional subtle safety degradation remains a challenge, we establish a baseline configuration for further work in this area. We release our auditing agent at https://github.com/safety-research/finetuning-auditor.

cs.CR↗

arXiv2025

The Attacker Moves Second: Stronger Adaptive Attacks Bypass Defenses Against Llm Jailbreaks and Prompt Injections

How should we evaluate the robustness of language model defenses? Current defenses against jailbreaks and prompt injections (which aim to prevent an attacker from eliciting harmful knowledge or remotely triggering malicious actions, respectively) are typically evaluated either against a static set of harmful attack strings, or against computationally weak optimization methods that were not designed with the defense in mind. We argue that this evaluation process is flawed. Instead, we should evaluate defenses against adaptive attackers who explicitly modify their attack strategy to counter a defense's design while spending considerable resources to optimize their objective. By systematically tuning and scaling general optimization techniques-gradient descent, reinforcement learning, random search, and human-guided exploration-we bypass 12 recent defenses (based on a diverse set of techniques) with attack success rate above 90% for most; importantly, the majority of defenses originally reported near-zero attack success rates. We believe that future defense work must consider stronger attacks, such as the ones we describe, in order to make reliable and convincing claims of robustness.

cs.LG↗

arXiv2025

Agentic Property-Based Testing: Finding Bugs Across the Python Ecosystem

Property-based testing (PBT) is a lightweight formal method, typically implemented as a randomized testing framework. Users specify the input domain for their test using combinators supplied by the PBT framework, and the expected properties or invariants as a unit-test function. The framework then searches for a counterexample, e.g. by generating inputs and calling the test function. In this work, we demonstrate an LLM-based agent which analyzes Python modules, infers function-specific and cross-function properties from code and documentation, synthesizes and executes PBTs, reflects on outputs of these tests to confirm true bugs, and finally outputs actionable bug reports for the developer. We perform an extensive evaluation of our agent across 100 popular Python packages. Of the bug reports generated by the agent, we found after manual review that 56\% were valid bugs and 32\% were valid bugs that we would report to maintainers. We then developed a ranking rubric to surface high-priority valid bugs to developers, and found that of the 21 top-scoring bugs, 86\% were valid and 81\% we would report. The bugs span diverse failure modes from serialization failures to numerical precision errors to flawed cache implementations. We reported 5 bugs, 4 with patches, including to NumPy and cloud computing SDKs, with 3 patches merged successfully. Our results suggest that LLMs with PBT provides a rigorous and scalable method for autonomously testing software. Our code and artifacts are available at: https://github.com/mmaaz-git/agentic-pbt.

cs.SE↗

arXiv2025

Poisoning Attacks on LLMs Require a Near-constant Number of Poison Samples

Poisoning attacks can compromise the safety of large language models (LLMs) by injecting malicious documents into their training data. Existing work has studied pretraining poisoning assuming adversaries control a percentage of the training corpus. However, for large models, even small percentages translate to impractically large amounts of data. This work demonstrates for the first time that poisoning attacks instead require a near-constant number of documents regardless of dataset size. We conduct the largest pretraining poisoning experiments to date, pretraining models from 600M to 13B parameters on chinchilla-optimal datasets (6B to 260B tokens). We find that 250 poisoned documents similarly compromise models across all model and dataset sizes, despite the largest models training on more than 20 times more clean data. We also run smaller-scale experiments to ablate factors that could influence attack success, including broader ratios of poisoned to clean data and non-random distributions of poisoned samples. Finally, we demonstrate the same dynamics for poisoning during fine-tuning. Altogether, our results suggest that injecting backdoors through data poisoning may be easier for large models than previously believed as the number of poisons required does not scale up with model size, highlighting the need for more research on defences to mitigate this risk in future models.

cs.LG↗

arXiv2025

Evaluating the Robustness of a Production Malware Detection System to Transferable Adversarial Attacks

As deep learning models become widely deployed as components within larger production systems, their individual shortcomings can create system-level vulnerabilities with real-world impact. This paper studies how adversarial attacks targeting an ML component can degrade or bypass an entire production-grade malware detection system, performing a case study analysis of Gmail's pipeline where file-type identification relies on a ML model. The malware detection pipeline in use by Gmail contains a machine learning model that routes each potential malware sample to a specialized malware classifier to improve accuracy and performance. This model, called Magika, has been open sourced. By designing adversarial examples that fool Magika, we can cause the production malware service to incorrectly route malware to an unsuitable malware detector thereby increasing our chance of evading detection. Specifically, by changing just 13 bytes of a malware sample, we can successfully evade Magika in 90% of cases and thereby allow us to send malware files over Gmail. We then turn our attention to defenses, and develop an approach to mitigate the severity of these types of attacks. For our defended production model, a highly resourced adversary requires 50 bytes to achieve just a 20% attack success rate. We implement this defense, and, thanks to a collaboration with Google engineers, it has already been deployed in production for the Gmail classifier.

cs.CR↗

arXiv2025

Defending Against Prompt Injection With a Few DefensiveTokens

When large language model (LLM) systems interact with external data to perform complex tasks, a new attack, namely prompt injection, becomes a significant threat. By injecting instructions into the data accessed by the system, the attacker is able to override the initial user task with an arbitrary task directed by the attacker. To secure the system, test-time defenses, e.g., defensive prompting, have been proposed for system developers to attain security only when needed in a flexible manner. However, they are much less effective than training-time defenses that change the model parameters. Motivated by this, we propose DefensiveToken, a test-time defense with prompt injection robustness comparable to training-time alternatives. DefensiveTokens are newly inserted as special tokens, whose embeddings are optimized for security. In security-sensitive cases, system developers can append a few DefensiveTokens before the LLM input to achieve security with a minimal utility drop. In scenarios where security is less of a concern, developers can simply skip DefensiveTokens; the LLM system remains the same as there is no defense, generating high-quality responses. Thus, DefensiveTokens, if released alongside the model, allow a flexible switch between the state-of-the-art (SOTA) utility and almost-SOTA security at test time. The code is available at https://github.com/Sizhe-Chen/DefensiveToken.

cs.CR↗

arXiv2025

IF-GUIDE: Influence Function-Guided Detoxification of LLMs

We study how training data contributes to the emergence of toxic behaviors in large language models. Most prior work on reducing model toxicity adopts reactive approaches, such as fine-tuning pre-trained (and potentially toxic) models to align them with human values. In contrast, we propose a proactive approach, IF-GUIDE, that leverages influence functions to identify and suppress harmful tokens in the training data. To this end, we first show that standard influence functions are ineffective at discovering harmful training records. We then present a novel adaptation that measures token-level attributions from training data to model toxicity, along with techniques for selecting toxic training documents and a learning objective that can be integrated into both pre-training and fine-tuning. Moreover, IF-GUIDE does not rely on human-preference data, which is typically required by existing alignment methods. In our evaluation, we demonstrate that IF-GUIDE substantially reduces both explicit and implicit toxicity-by up to 10$\times$ compared to uncensored models, and up to 3$\times$ compared to baseline alignment methods such as DPO and RAD-across both pre-training and fine-tuning scenarios. IF-GUIDE is computationally efficient: a billion-parameter model is not necessary for computing influence scores; a million-parameter model-with 7.5$\times$ fewer parameters-can effectively serve as a proxy for identifying harmful data. Our code is publicly available at: https://github.com/ztcoalson/IF-Guide

cs.LG↗

arXiv2025

LLMs unlock new paths to monetizing exploits

We argue that Large language models (LLMs) will soon alter the economics of cyberattacks. Instead of attacking the most commonly used software and monetizing exploits by targeting the lowest common denominator among victims, LLMs enable adversaries to launch tailored attacks on a user-by-user basis. On the exploitation front, instead of human attackers manually searching for one difficult-to-identify bug in a product with millions of users, LLMs can find thousands of easy-to-identify bugs in products with thousands of users. And on the monetization front, instead of generic ransomware that always performs the same attack (encrypt all your data and request payment to decrypt), an LLM-driven ransomware attack could tailor the ransom demand based on the particular content of each exploited device. We show that these two attacks (and several others) are imminently practical using state-of-the-art LLMs. For example, we show that without any human intervention, an LLM finds highly sensitive personal information in the Enron email dataset (e.g., an executive having an affair with another employee) that could be used for blackmail. While some of our attacks are still too expensive to scale widely today, the incentives to implement these attacks will only increase as LLMs get cheaper. Thus, we argue that LLMs create a need for new defense-in-depth approaches.

cs.CR↗

arXiv2025

Defeating Prompt Injections by Design

Large Language Models (LLMs) are increasingly deployed in agentic systems that interact with an untrusted environment. However, LLM agents are vulnerable to prompt injection attacks when handling untrusted data. In this paper we propose CaMeL, a robust defense that creates a protective system layer around the LLM, securing it even when underlying models are susceptible to attacks. To operate, CaMeL explicitly extracts the control and data flows from the (trusted) query; therefore, the untrusted data retrieved by the LLM can never impact the program flow. To further improve security, CaMeL uses a notion of a capability to prevent the exfiltration of private data over unauthorized data flows by enforcing security policies when tools are called. We demonstrate effectiveness of CaMeL by solving $77\%$ of tasks with provable security (compared to $84\%$ with an undefended system) in AgentDojo. We release CaMeL at https://github.com/google-research/camel-prompt-injection.

cs.CR↗

arXiv2025

In-House Evaluation Is Not Enough: Towards Robust Third-Party Flaw Disclosure for General-Purpose AI

The widespread deployment of general-purpose AI (GPAI) systems introduces significant new risks. Yet the infrastructure, practices, and norms for reporting flaws in GPAI systems remain seriously underdeveloped, lagging far behind more established fields like software security. Based on a collaboration between experts from the fields of software security, machine learning, law, social science, and policy, we identify key gaps in the evaluation and reporting of flaws in GPAI systems. We call for three interventions to advance system safety. First, we propose using standardized AI flaw reports and rules of engagement for researchers in order to ease the process of submitting, reproducing, and triaging flaws in GPAI systems. Second, we propose GPAI system providers adopt broadly-scoped flaw disclosure programs, borrowing from bug bounties, with legal safe harbors to protect researchers. Third, we advocate for the development of improved infrastructure to coordinate distribution of flaw reports across the many stakeholders who may be impacted. These interventions are increasingly urgent, as evidenced by the prevalence of jailbreaks and other flaws that can transfer across different providers' GPAI systems. By promoting robust reporting and coordination in the AI ecosystem, these proposals could significantly improve the safety, security, and accountability of GPAI systems.

cs.AI↗

arXiv2025

AutoAdvExBench: Benchmarking autonomous exploitation of adversarial example defenses

We introduce AutoAdvExBench, a benchmark to evaluate if large language models (LLMs) can autonomously exploit defenses to adversarial examples. Unlike existing security benchmarks that often serve as proxies for real-world tasks, bench directly measures LLMs' success on tasks regularly performed by machine learning security experts. This approach offers a significant advantage: if a LLM could solve the challenges presented in bench, it would immediately present practical utility for adversarial machine learning researchers. We then design a strong agent that is capable of breaking 75% of CTF-like ("homework exercise") adversarial example defenses. However, we show that this agent is only able to succeed on 13% of the real-world defenses in our benchmark, indicating the large gap between difficulty in attacking "real" code, and CTF-like code. In contrast, a stronger LLM that can attack 21% of real defenses only succeeds on 54% of CTF-like defenses. We make this benchmark available at https://github.com/ethz-spylab/AutoAdvExBench.

cs.CR↗