Matthew Jagielski

Jailbreaking Jailbreaks: A Proactive Defense for LLMs

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.

Untrusted Content Masking for Web Agents with Security Guarantees

Defenses that provide security guarantees against prompt injection attacks rely on strict isolation between trusted instructions and untrusted data. In text-based environments such as tool-use APIs, this separation arises naturally: agents can reason from interface definitions without ever processing untrusted content. Extending these guarantees to web agents faces a fundamental challenge: to perceive and interact with their environment, web agents must first observe the rendered page, which intermingles trusted content with untrusted content. This structural entanglement removes the trust boundary on which security guarantees depend, undermining provable defenses for web agents. In this paper, we present Untrusted Content Masking (UCM), a simple and effective approach that restores this boundary in web environments. We leverage a key structural insight: a webpage's Document Object Model (DOM) encodes sufficient information to distinguish trusted from untrusted regions without reading their content. Our framework exploits this by redacting untrusted regions before they reach the agent and routing interaction through a sandboxed interface with strict privilege separation, thereby enabling agents to observe and interact with their environment while remaining isolated from adversarial content. The code is publicly available.