Chai: Agentic Discovery of Cryptographic Misuse Vulnerabilities
Authors: Corban Villa, Sohee Kim, Austin Chu, Alon Shakevsky, Raluca Ada Popa
Organizations: UC Berkeley
Abstract
AI-assisted vulnerability discovery has proven effective for bug classes like memory safety, where instrumentation confirms memory violations and efficiently filters false positives. Many dangerous vulnerability classes, such as cryptographic misuse, however, lack any comparable instrumentation. In this work, we present Chai, an AI-based system that discovers and validates cryptographic misuse vulnerabilities through naturally occurring signals. To achieve this, Chai rethinks the classical technique of differential testing by leveraging AI to 1) improve precision for detecting real security issues in libraries, and 2) repurpose commonly overlooked discrepancies as leads for tangible vulnerabilities in downstream applications. In doing so, Chai inverts the prevailing paradigm of AI vulnerability discovery: instead of auditing one codebase for many flaws, it catalogs flaws at the library level and propagates them across a cryptographic dependency graph, delivering compounding efficiency gains. We evaluate Chai across X.509, JWT, and SAML libraries. Chai discovered a previously unknown critical vulnerability in an SSL library that powers billions of devices, along with security bugs in one library behind a major web browser and another in major Linux distributions. In total, these techniques surfaced over 100 vulnerabilities.
LLM-based analyzers have begun finding real vulnerabilities in mature open-source projects: AISLE's analyzer is credited with more than 280 CVEs across 78 projects, including OpenSSL, curl, and GnuTLS. We introduce HoF-Bench (named after AISLE's public Hall of Fame), a benchmark built from 95 of these public AI-discovered CVEs across eight repositories pinned at vulnerable commits. Analyzers receive source and target-file scope but not CVE identifiers, descriptions, fixes, or expected mechanisms; a detector-blinded frontier-model judge credits only findings that identify the same code path, root cause, attack condition, and impact. A deliberately minimal LLM-based analyzer rediscovers up to 65 of the 95 CVEs (68%) under this strict protocol. No frontier model performs detection anywhere in the study. The ten detector backbones are five open-weight models (21B--284B total parameters, 3--13B active) and five proprietary small or "flash"-tier models. All of them run in the fixed scaffold with four repeated passes, an optional generated-context stage, and a replayable multi-round triage stage (7,600 model--CVE pass records). Difficulty is strongly structured by language; the CVEs missed by every model concentrate in C infrastructure code. HoF-Bench provides a compact test bed for comparing vulnerability scanners, their reliability across repeated runs, and the candidate volume they create. The dataset is available at https://huggingface.co/datasets/aisleinc/HoF-Bench.
AI has the potential to transform cybersecurity by enabling systems that can autonomously detect, analyze, and remediate software vulnerabilities. However, existing cybersecurity evaluations of AI systems are limited in scale or scope, and fail to capture the end-to-end lifecycle of real-world software vulnerability discovery and remediation. To address this gap, we propose CyberGym-E2E, a large-scale and realistic end-to-end cybersecurity benchmark that comprehensively evaluates AI agents' abilities across the full lifecycle of vulnerability discovery, PoC generation, and patch generation. CyberGym-E2E is comprehensive and scalable, as we build an automated, agent-enhanced pipeline for transforming open-source vulnerability data into realistic evaluation environments. Currently, the benchmark consists of 920 real-world vulnerabilities across 139 different open-source projects.
The advent of agentic vulnerability detection is already becoming a watershed moment for software security. Audits conducted entirely by autonomous LLM agents are uncovering critical vulnerabilities in fundamental software underpinning digital society. Many of these vulnerabilities remained masked for years, surfacing only now with AI agents. Yet the reasoning behind these discoveries remains alarmingly opaque and unvalidated. What assumptions did the agent make about a function's inputs when it deemed that function to be secure? Failures in reasoning and incorrect assumptions can lead to missed vulnerabilities and reduce trust in agentic analysis. We propose a security-specification-first paradigm that (1) exposes the agent's tacit assumptions explicitly as security specifications and (2) continuously refines those specifications via runtime falsification. We realize our approach in Code-Augur, a novel harness for agentic vulnerability detection. Given a codebase, Code-Augur analyzes each component of the system for vulnerable code. When it deems a component to be secure, it commits the local invariants behind that judgment as in-source assertions. In parallel, Code-Augur leverages a guided fuzzer to attempt to falsify those assumptions. When the fuzzer triggers an assertion, this either reveals a genuine vulnerability or a flawed specification to refine. In both cases, this process grounds the agent's understanding, aligning its view of code intent with how the code actually behaves. On real-world subjects, Code-Augur effectively leverages security specifications to detect more vulnerabilities than other state-of-the-art agents. Additionally, Code-Augur found 22 new vulnerabilities in key open-source projects. Compared to curated specialized models like Claude Mythos, Code-Augur offers effective agentic vulnerability detection built on widely available LLMs like Sonnet and DeepSeek.